sailboat rides portland maine

Sailing daily from Fore Points Marina beginning in May 2024!

Relax and enjoy the best views of Portland aboard Nautilus

Grab your favorite bottle of wine and step aboard for an experience you'll always remember. Sail past lighthouses, the historic Fort Gorges, and learn about the rich history of Portland Harbor from our seasoned and passionate crew.

Sail Casco Bay with Us

Book a sailing adventure for a day trip, sunset cruise or your own private charter in Portland, Maine!

11:00 AM - 1:00 PM | Morning Sail

3:00 PM - 5:00 PM | Afternoon Sail

$80 per Person | $450 Private Charter

Public sails depart daily to explore Maine’s diverse and scenic Portland Harbor.

Choose our first trip for a calm morning outing, or join us in the afternoon when the wind picks up. Get on the water with Nautilus Sailing Company for a uniquely memorable Portland, Maine excursion.

SUNSET SAILS

6:00 - 8:00 PM | Sunset Sail

Fall Hours May Vary

$95 per Person | $550 Private Charter

Public sunset sails depart each evening to enjoy golden hour views of Maine’s diverse and scenic Portland Harbor.

Bring your camera and favorite cocktail and get on the water with Nautilus Sailing Company to enjoy the best sunset views of Portland, Maine.

CUSTOM CHARTERS

Starting at $450 |  Call for a Quote

Need an extra hour or some additional flexibility? From intimate wedding ceremonies, to memorable anniversary celebrations, to unique bachelor and bachelorette parties, to corporate outings, our custom private charters are fully customizable to meet your needs.

Call to plan your ideal Portland Harbor sail charter and make your next special event epic!

BOOKING CALENDAR

Have a date in mind? View our Booking Calendar below:

Designed and built to look and feel like the sailing vessels of days gone by, our 37' ketch Nautilus perfectly combines traditional form and modern function.

With a large cockpit and wide cabin tops, you'll find plenty of comfortable seating options for all. The spacious cabin offers ample space for lounging, eating, or a brief respite from the elements. The galley has all the amenities of home, including an ice box and stove, and there is also a large head with push button facilities-- everything you need to create your ideal Portland excursion. Join us! We're certain you'll be glad you did.

Step aboard the sailboat Nautilus and experience the real magic of Casco Bay.

Relax and unwind as we silence the motor and let the wind take us sailing past lighthouses, between the islands, past historic forts, and even alongside playful porpoises and seals. With Captain Sam and first mate Crow as your seasoned guides, sit back and enjoy the view while you learn about our treasured Maine coast.

• What is the maximum passenger capacity? Nautilus's passenger capacity is 6 people maximum. This is determined by the U.S. Coast Guard so it is not flexible.
• Do infants count towards passenger capacity? Yes. The passenger limit is based on the number of lives aboard, rather than by seating room.
• Do you take same-day bookings? YES we do! Our booking software with FareHarbor allows for same-day bookings. If a sail during a time slot you are interested in appears to be greyed out, you can give us a call to see if there are any seats remaining. One important thing to note: if the crew are not currently on the boat, it will take us roughly one hour to arrive at the boat and complete an all-systems safety check, so please call as far in advance as possible.
• Is alcohol allowed on board? Yes! Please bring your favorite beverage (BYOB). For maximum Maine immersion, pick up some locally made favorites from Portland’s incredible craft brewery scene, like Bissel Brothers, Rising Tide, Belleflower, and Liquid Riot (or any from almost two dozen other local breweries - you can’t go wrong). For those who don’t like beer, seek out Maine Craft Distilling’s Blueshine Lemonade or Après’ Pine Rickey hard seltzer for a uniquely Maine flavor!
• Will we tip (heel) over? As a sailboat, the Nautilus is designed to lean to one side or the other with the pressure of the wind in her sails, with the extent of that heeling depending on the strength of the wind. If you’d like a more spirited sail, we recommend checking the forecast for winds of 13 knots (roughly 15 miles per hour) or higher. Morning and Sunset Sails tend to be the calmest, while Afternoon Sails are generally more lively. In Portland we usually receive the strongest winds in May, June, September, and October, while July and August are the calmest months.
• Is there a bathroom on board? Yes! We have a marine toilet, also called a head. The marina also has facilities for all guests in the form of 3 single-stall restrooms.
• Are there any amenities or utensils on board? We can provide bottled water, napkins, paper plates, utensils, and cups.
• Is smoking allowed on board? No, we don’t allow smoking while on the vessel.
• Is cannabis/marijuana allowed on board? Despite Maine’s decriminalization of recreational cannabis, we’re afraid we cannot allow any federally banned drug on board the vessel at this time. Our business, like all other U.S.-based commercial marine activity, is regulated by the US Coast Guard and as such must obey Federal law. If you do enjoy some of Portland’s many dispensaries, we ask you not to indulge while you’re out sailing with us.
• What is your general cancellation policy? Please cancel one week in advance of your sail to receive a full refund. Cancellations made with under one week’s notice will not receive a refund unless they are due solely to sudden illness (see covid-19 policy below).
• What happens if it rains? In the event of poor weather or unsafe conditions determined by the Captain at the time of the sail, a full refund will be issued.
• Do you have a covid-19 / illness refund policy? If you become sick with covid-19, the flu, or any other contagious illness and need to cancel, you will receive a full refund. We appreciate your help in not spreading any illnesses to the crew!

Reserve Now

Reserve tickets with Sail Portland Maine for the most beautiful boat cruise on the Casco Bay. We offer daily two-hour public or private trips where you’re guaranteed a crowd-free, intimate, and unique adventure aboard our sailboat, Eleanor Hawkes , or our Classic Motor Yacht, the Calista Ann ! 

Your Guide to the BEST Maine Sailing Tours | Windjammers, Sailboats, & Schooner Tours

Everyone knows that Maine has a stunning coastline and breathtaking views of the Atlantic Ocean from pristine beaches to rugged cliff walks. But, have you ever considered seeing Maine from the water? Set sail on an exciting adventure on one of the best Maine sailing tours onboard a windjammer, sailboat, or schooner.

We think it’s the best way to view the Maine coast , and what could be more exhilarating than setting sail out of a Maine harbor aboard a tall-masted schooner? Down the coastline from the Downeast & Acadia region to the Southern Maine Coast , there are so many sailing excursions to choose from.

The best part? You can sit back and relax while someone else does the sailing and navigating. Or, you may lend a hand and hoist a sail if you prefer. There’s no better way to experience the beauty of Maine than on a historic sailing trip, so check out these options for your next visit to Maine.

Downeast & Acadia Sailing Tours

Downeast windjammer cruise lines.

If you’re looking for a variety of options for sailing, Downeast Windjammer Cruise Lines in Bar Harbor has you covered. Offering a Sunset Sail, a Morning Sail, and an Afternoon Sail, there’s a wonderful experience no matter the time of day. Each sail has its own vibe.

The Sunset Sail is the most popular cruise that Downeast offers. It includes live folk music, beer, and wine for sale. Or, enjoy sailing in Frenchman Bay during the Morning Sail, which is more relaxed but still offers breathtaking views of Acadia National Park .

The Afternoon Sail is perfect for those looking for a narration during the sail. The captain will point out points of interest, regale you with the local history, and discuss wildlife.

No matter the sail, you can bring a picnic of snacks along, and most sails are pet-friendly.

Downeast Sailing Adventures

Southwest Harbor

Step aboard the Real Maine for an unforgettable experience sailing around the Cranberry Islands, Acadia, and Somes Sound. This tour will take you by lighthouses, past gorgeous homes on the shore, and by working fishing boats.

Book a private charter or a group day sailing adventure for up to six passengers. Downeast Sailing Adventures has daily sails on its 33-foot boat Surprise and its 38-foot boat Swan .

Sail Acadia

Northeast Harbor & Southwest Harbor

Sail Acadia offers trips out of two harbors, Northeast Harbor and Southwest Harbor . Sailing trips can be either shared or privately chartered. Private charters can be catered to your preferences with sailing instructions or a stop at an island for a picnic included.

Book a morning sail for calm waters with gentle sea breezes and good opportunities to view local wildlife. The morning sail is suggested for first-timers and children.

Or, book an afternoon sail for stronger winds that will make the sailboat cruise faster. This sail typically sees seals along the route, and the captain will often give a narration of the wildlife and history of the area.

Another option is a sunset sail for a romantic experience. This sail will have you seeing gorgeous sunset views on calm waters.

Schooner Tours in MidCoast Maine

Schooner stephen taber.

If you’re looking for an all-inclusive overnight experience, book a sail aboard the 150-year-old Stephen Taber . Each sail includes accommodations in one of 12 cabins, meals, wine (on evening sails), a lobster bake and barbecue on the beach, and evening entertainment.

Guests can choose from a themed trip or a private charter from Rockland Maine . Themed trips are a lot of fun and span from three to six nights, depending on your preference.

Enjoy trips such as Culinary Explorations; ‘Wine, Dine, and Chocolate;’ Yacht Racing Regatta; Penobscot Bay’s Hidden Gems; and more. These trips are sure to be memorable experiences, and by the end of the trips, you’ll feel like family with the other guests on board.

Here are more MidCoast Maine boat tours that are part of the Maine Windjammer Association like the Schooner Stephen Taber : Schooner American Eagle | Captain Tyler King | Rockland, ME Windjammer Angelique | Captain Dennis Gallant & Candace Kuchinski | Camden ME Schooner Grace Bailey | Captain Sam Sikkema | Rockland, ME Schooner Heritage | Captains Sean Grims & Ben Welzenbach | Rockland, ME Schooner Ladona | Captain J.R. Braugh  | Rockland, ME Schooner Lewis R. French | Captain Becky Wright and Nathan Sigouin | Camden, ME Schooner Mary Day | Captain Barry King and Jen Martin | Camden, ME

A Morning in Maine

If you’re strapped for time and want a shorter sail, A Morning in Maine’s sailing trips are a wonderful experience. The two-hour sailing adventures take place aboard a 55-foot ketch that passes lighthouses and other schooners.

The morning trip is perfect for those looking for calm sailing. The mid-afternoon sail has windier conditions for a faster sail. Evening and sunset sails feature beautiful sunset views and a relaxing ride. Guests are often given the chance to try to steer the boat as well.

Schooner Surprise

The Schooner Surprise has been sailing for over 105 years, with 30 of those years setting sail out of Camden Maine . Guests can book a two-hour sail with views of the lighthouse, summer houses and views of Penobscot Bay .

These family-friendly sails let guests, including children, take the wheel while out at sea. Special sails include a Full Moon Sail that features live music during sunset and a trip lasting two hours into the night. Or, book a fireworks view sail or a Birding and Marine Life Tour with an ornithologist.

Portland & Casco Bay Sailing Tours

Portland schooner co..

Portland Schooner Co. sets sail from Portland Maine and cruises through Casco Bay for a delightful trip along the coastline and past lighthouses and ocean life, like seals. On the two-hour sail, bring your own picnic and even alcoholic beverages for a relaxing, scenic time on the water.

These sails are perfect for all ages. Sails take place throughout the day on one of the five historic wooden schooners. The sails are relaxing and do not include narration, but the crew is available to answer any questions that guests may have.

Maine Sailing Adventures

Maine Sailing Adventures offers traditional two-hour and themed sails through Casco Bay . What sets it apart from other sailing companies is its unique themed sails. Try an acoustic sail that features live music. Or, try a wine sail that includes a wine tasting for adults.

Have you ever heard of a yoga sail? This ship can accommodate up to 12 guests for a yoga class that you won’t experience anywhere else. Enjoy amazing views of the water while working on your poses.

Sail Portland Maine

If you’re looking for an intimate sailing adventure, Sail Portland Maine has you covered. Guests can choose a private charter or a public trip. The public trips’ capacity is 12 people, so you know that your sail won’t be too crowded.

Day and sunset trips are two hours in length and pass by all of the famous Casco Bay features — like historic forts, lighthouses, and if you’re lucky to spot them, seals. Guests are welcome to bring their own food and drinks, while bottled water is complimentary on board.

Schooner Tours on the Southern Maine Coast

The pineapple ketch.

Kennebunkport

There’s no better way to see the Kennebunk River than sailing on it. The Pineapple Ketch departs from Nonantum Resort for a dazzling trip along the river and the Kennebunkport coastline.

You’ll see gorgeous seasonal cottages, including the famous cottage of President George H.W. Bush. Enjoy views of the Goat Island Lighthouse, local harbors, seabirds, and seals.

Each sail includes complimentary bottled water and sodas, but guests are also welcome to bring their own food and beverages.

Silverlining Sailing

Silverlining Sailing offers one of the most intimate sails in Ogunquit Maine . Each boat has the capacity for up to six passengers, making for a small group sail. Sails typically last two hours, departing from the quaint Perkins Cove village.

There are five trips daily (weather permitting) from early morning through to a sunset sail in the evening. Enjoy stunning ocean views, gorgeous waterfront homes, views of local beaches, and harbors.

Since this is a smaller group sail, guests get the opportunity to try their hand at taking the wheel and steering the schooner.

Broad Reach Adventures

Broad Reach Adventures has two-hour sails, half-day and full-day sails, and chartered sails from Saco Maine , so there’s a sail to accommodate your busy schedule.

Each one allows guests to see beautiful views of the Saco River, Saco Bay, Biddeford Pool, Old Orchard Beach , and lighthouses along the way. Longer sails provide guests with the opportunity to disembark and explore uninhabited islands.

A unique feature that Broad Reach Adventures offers is the opportunity to add a massage or professional photographer. These experiences are available on certain dates and times, so book ahead if you’re interested in these add-ons.

Sailing Lessons & Boat Rentals

If you want to learn to sail, sailing instruction is often available as part of your charter package.  Private charters  of sailboats on the Maine coast allow experienced sailors to explore the coastline on their own.

Private sailors will find  hotel marinas  for lodging in Maine’s best harbors. If you time your sailing cruise right, you might witness seals, porpoises, whales, or other tall ships.

Watching the sunrise from the deck of a schooner is one of life’s simplest, most satisfying pleasures. Of course, the spectacular Maine scenery is always included on your sail.

Set Sail on Sailboat & Schooner Tours From Maine This Season

Now that you know about all of the sailing trip options, it’s time to set sail into the open waters of Maine. From two-hour trips of the bays and harbors to overnight excursions, there’s an experience awaiting you on your next getaway.

Each Maine sailing company offers its own unique trips aboard safe, well-maintained schooners. Relax, unwind, and feel the ocean breeze in your hair as you cruise through the lapping waves of Maine’s Atlantic shoreline.

The VisitMaine.Net team is the small team of authors and editors that research and write our in-depth guides throughout the site and update past articles to make sure they're still super valuable to you. We have one goal: to help you fall more in love with the state of Maine!

Similar Posts

9 Breathtaking Winter Hikes in Southern Maine

Winter hikes in Southern Maine aren’t just along beautiful beaches, but who are we kidding? That’s one of the best parts! The great thing…

Maine Tides and Tide Chart Resources

Maine tides are like Maine weather, constantly changing. Mainers who depend on the water need to know the ebb and flow. For your Maine…

Guide to Wells Maine Condominium Resorts

Wells is a well-loved vacation town in Maine. You name, it you can enjoy it in Wells. Miles of sandy beaches – check, amusement parks –…

Guide to Hotels, Bed and Breakfasts, Vacation Rentals, & Other Lodging in Harpswell Maine

Renowned for its rugged beauty and maritime charm, Harpswell Maine offers a serene getaway with a network of over 200 offshore islands within Casco…

ULTIMATE Guide of Things to Do in Kennebunkport Maine

Looking for the best things to do in Kennebunkport Maine? We’ve got you covered with the best attractions, activities, dining, lodging, and more! Kennebunkport…

16 Delicious Restaurants in Sanford Maine

Sanford Maine is a beautiful, scenic city in Maine that offers walking trails and views of historic mills and factories. But, did you know…

Leave a Reply Cancel reply

Your email address will not be published. Required fields are marked *

Save my name, email, and website in this browser for the next time I comment.

VisitMaine.Net – The unofficial guide to exploring the great state of Maine. Not affiliated with any official tourism entities.

Copyright VisitMaine.Net 2023 Images Courtesy Greg and Heather Burke unless otherwise noted.

Portland, Maine Historic Fort & Lighthouse Tours

Family friendly civil war fort tours, maine’s iconic lighthouses tour, and 21+ sunset cruises. a local craft beer, canned cocktail, or wine is included for every guest.

• Most Popular!
• User All Ages
• Hour Glass 2 Hours

Fort Tour on a Private Island

Casco Bay’s stone fortresses are captivating characters in the story of Maine history. For the first time, SeaPortland is bringing you to the historic site Fort Scammel via the Elizabeth Grace . Join us for a boat tour no other Portland harbor tour company can offer.    

• Hour Glass 1.5 Hours

Sunset Lighthouse Harbor Cruise

 There is nothing quite like a Maine sunset, especially from the water . Aboard the Elizabeth Grace , with local craft beers in hand, we will take you on a stunning journey through the waters of Casco Bay. Don’t miss this tour!

Scenic Lighthouse Harbor Tour

This epic tour is the best way to take in the historic lighthouses, stone forts, and rocky islands that make Casco Bay a world-renowned destination.

SeaPortland brings you straight into the heart of authentic Maine.

Aboard the Elizabeth Grace and other vessels in our fleet, we show you the parts of Casco Bay unseen by most. We provide experiences that strike at the heart of what makes this part of the world so magical.

Join us for boat tours of previously unexplored early nineteenth-century forts. Bathe in the warm lights of a summer sunset over the water. Breathe in the ocean air while viewing Maine’s famous lighthouses. Toast local craft beverages. What could be better?

Join us for a tour today.

• Chevron down Is there a head (bathroom) on the boat?

There is no bathroom on board the boat. We highly recommend using the facilities before boarding.If you are on the Private Island Fort Tour there is a bathroom on the island.

• Chevron down Can I purchase more drinks on the boat?

No, this is a sightseeing/historical focused tour that happens to include one drink (Fort Tour) or two drinks (Lighthouse and Sunset cruise). If we catch a group trying to sneak more drinks we will end the tour immediately for those in the party.

• Chevron down Should I tip the crew?

Yes. The boat crew is there to help keep you safe and to tell you about the sights in the harbor. They work hard to make it a great experience. Treat them with respect and listen to them. The crew will split tips and for those wondering 20% is the common amount.

• Chevron down Can we bring our own alcohol on board?

No, we have our own license that prohibits guests from bringing their own alcohol on the boat.

• Chevron down Can we bring food on board?

Yes, feel free to bring food on board. We just ask that you also take any trash away with you as well.

• Chevron down Do we have to be 21 to take a tour?

Yes for our Lighthouse and Sunset Tour you must be 21. If you want to book a private charter please contact us and we can work with you if you have people in the group under 21. For our Fort Tour it is great for all ages.

• Chevron down What should I wear?

Dress appropriately for the weather. We will have a canopy which will protect you from direct sunlight and rain, however it can be significantly cooler out on the water so we recommend bringing a jacket. On the Fort Tour we highly encourage closed toed shoes.

• Chevron down Where should I park?

Street parking has a maximum of 2 hours. Many lots are privately owned, and most of those are managed by a professional parking company. There are a couple of lots very close to the departure location, and an interactive map of parking options close by can be found here at Parkopedia . 20 Custom House Wharf – There is a small pay by the hour lot at our point of departure. This is first come first serve.

• Ocean Gateway city lot – 2 Commercial St, Portland. (Seasonal: April through October) $15.00 per 24 hour period. Pay at the kiosk or through the Passport App with a credit card and display the receipt face up inside on the vehicle’s front dashboard.
• Hub Furniture private lot – 291 Fore St, Portland (typically no more than $15/day)
• Simba Parking private lot – 216 Fore St, Portland (typically no more than $15/day)
• Fore Street Parking Garage – 427 Fore Street, Portland
• Fisherman’s Wharf private lot – 202 Commercial Street, Portland
• Custom House Parking Garage – 25 Pearl Street, Portland
• Chevron down Will the tour get cancelled?

Our tours run rain or shine as long as wind and sea conditions are deemed by the captain to be safe. The Elizabeth Grace is set up to keep guests sheltered in case of wet or windy weather. We watch the weather forecasts closely, and if we are concerned conditions will not be favorable or safe, we will contact you ahead of time. This is New England and weather changes quickly so sometimes this can happen right before the tour.

We may also have to cancel if we do not meet our minimum requirement to operate. Again we will be in touch with you to discuss options.

• Chevron down What is your Cancellation Policy?

We operate rain, shine, as long as the waters are safe and we have met our minimum number of guests to operate the tour.

All ticket sales are **final.** Tours cannot be exchanged, rescheduled, or refunded. But life happens! We offer ticket insurance for public tours which allows you to cancel or reschedule your tour with at least 24 hours’ notice, and we will reschedule or reimburse you for your full tour ticket price (minus ticketing fee and insurance fee).

**Private Tours:** Cancellation of a private tour for any reason 5 days or more (120 hours or more before tour start time) will result in the forfeiture of the full non-refundable deposit amount. Cancellations of private tours for any reason under 5 days will result in the agreed amount of the full tour charged to the booking party.

THE 10 BEST Portland Boat Rides & Cruises

Boat rides & cruises in portland.

• Fishing Charters & Tours
• Kayaking & Canoeing
• Speed Boats Tours
• Surfing, Windsurfing & Kitesurfing
• Dolphin & Whale Watching
• Up to 1 hour
• 1 to 4 hours
• 4 hours to 1 day
• 5.0 of 5 bubbles
• 4.0 of 5 bubbles & up
• 3.0 of 5 bubbles & up
• 2.0 of 5 bubbles & up
• Portland Head Light
• Spring Point Ledge Lighthouse
• Fort Gorges
• Likely to Sell Out
• The ranking of tours, activities, and experiences available on Tripadvisor is determined by several factors including the revenue generated by Tripadvisor from these bookings, the frequency of user clicks, and the volume and quality of customer reviews. Occasionally, newly listed offerings may be prioritized and appear higher in the list. The specific placement of these new listings may vary.

1. Harbor Lights and Sights Cruise

2. Private Island Fort Tour in Casco Bay: Boat Cruise & Island Tour

3. Sunset Lighthouse Harbor Cruise from Portland's Old Port

4. Lighthouse Lovers Cruise in Portland

5. Maine Whale Watching Tour in Portland

6. Portland Tall Ship Cruise on Casco Bay

7. Sunset Sea Kayak Tour of Casco Bay

8. Seven Portland Lighthouses Tour

9. Guided RIB Boat Adventure of Casco Bay

10. Private Lighthouse Sightseeing Charter on a Vintage Lobster Boat

11. Sunset Lighthouse Cruise Tour from Casco Bay

12. Scenic Lighthouse Boat Cruise from Portland's Old Port

13. Private Sunset Charter on a Vintage Lobster Boat

14. Mere Point Oyster Farm Tour

15. Half Day Private Boat Charter from Portland

16. New England Fall Foliage Private Lobster Boat Cruise

17. Stand Up Paddleboard Tour with Complimentary Oyster Tasting

18. Special Times Casco Bay Sunrise or Sunset Cruise

19. Stand-Up Paddle Sunset Tour in Portland

20. Portland Tall Ship Private Charter on Casco Bay

Keep the fun going with other experiences in the area.

Luxury Catamaran Sailing Charters in Maine

Schooner Applejack Sunset Sail Tour in Boothbay Harbor

Schooner Apple Jack 2-Hour Day Sail from Boothbay Harbor

Scenic Sebago Lake Historical Tour by Kayak

Fall Covered Bridge Kayak Tour, Southern Maine

Sail Away: Explore Maine's Coastal Beauty on a 2-Hour Excursion

Golden Hour Escape: Private Sunset Sail in Coastal Maine

Sea Kayak to an Island Tour in Casco Bay

Discover Maine's Coastal Charms: Half-Day Scenic Sail

Sunset Tour by Kayak on Sebago Lake Maine

What travelers are saying.

Private Boat Tours and Island Adventures

Inquire about our tours.

Email Address

Interested In Interested In Family Adventures and Island Fort Excursions Maine Craft Beer Cruises Old Port Waterfront Tours Private Harbor and Lighthouse Tours

About Old Port Charters

Kids will enjoy exploring the island forts and geocaching treasure hunts on our interactive boating trips to multiple islands in Casco Bay. Adults can hop on board for a Maine craft beer cruise around the waterfront or our famous island bar hopping booze cruise.

Our Featured Charter Tours

Family Adventures and Island Fort Excursions

Maine Craft Beer Cruises

Private Harbor and Lighthouse Tours

Old Port Waterfront Tours

Private boat rides in the Old Port with fantastic up close views of Portland’s working waterfront.

Best Harbor Tours

Fun day exploring Fort Gorges.

Harbor Tours Portland Maine

A beautiful day for a lighthouse tour!

What Past Customers Say

Casco Bay Custom Charters

Embark on an unforgettable journey: customizable private boat charters & tours of casco bay, celebrating a decade on the water.

Experience Casco Bay’s Splendor with Our Private Boat Charters & Tours. 

At Casco Bay Custom Charters, we invite you to explore the captivating beauty of Maine from the unique vantage point of our classic wooden vessels. For the past decade, we’ve shared more than just boat tours. Our charters are personal introductions to the coastal landscapes, lighthouses, and culinary delights that define our region. 

With a focus on customization, each voyage with us is tailored to uncover the genuine essence of Casco Bay, enhanced by our commitment to exceptional service. Led by experienced crews passionate about sharing their knowledge and love for Maine, we ensure your journey is not only enjoyable but truly memorable.

SEARCH CHARTERS BY GROUP SIZE

Designed for exclusivity, our charters accommodate intimate groups of up to 6 guests or larger gatherings of 7-16. Our friendly captains and knowledgeable stewards ensure a personalized boating experience.

Small Groups aboard MONHEGAN

Intimate cruises for up to 6 on a vintage lobster boat

Learn More »

Large Groups aboard MARIE L

Classic coastal tours for up to 16

DINING CHARTERS

The best way to eat locally-sourced Maine cuisine is aboard our Dining Charters. Specialty menu dining charters, chef’s dinner sunset cruises, and bottomless mimosa brunch cruises available. Local catering and all-inclusive drink upgrades are available aboard EVERY Casco Bay Custom Charter!

Private Sunset Dinner Cruise

Small Groups (up to 6 guests) aboard MONHEGAN

Bottomless Mimosas & Croissant Brunch

Large Groups (7-16 guests) aboard MONHEGAN

ELOPE ON A PRIVATE ISLAND

Experience the magic of saying ‘I do’ on a private island with our Fortland Elopement Package. Escape to Fortland for an intimate, and unique wedding ceremony set against the backdrop of a stunning coastal landscape. An unforgettable way to share your vows and begin your new adventure in love

FORTLAND ISLAND ELOPEMENT PACKAGE

Unique, intimate wedding ceremonies on Fortland.

SAIL WITH GLEAM

For a limited-time, we’re partnering with GLEAM to offer sailing charters off the coast of Maine. GLEAM is a fully restored vintage 12 meter yacht that hosts up to 13 guests. Each captivating sailing excursion includes captain and crew for an effortless Maine summer sail.

GLEAM Private Sailing Charters

Sailing Excursions along Maine's Coast

CREATE YOUR OWN CUSTOM CHARTER

Tailor any of our curated tours and experiences for your group’s needs, from corporate bleisure to family-friendly outings and celebrations. Collaborate with our team to craft your perfect day, selecting from diverse food, beverage, and tour itinerary options. Your bespoke Maine adventure awaits.

Unforgettable 5-Star Maine Experiences ⭐⭐⭐⭐⭐

Embrace authentic maine with casco bay custom charters.

Journey with us and unlock the essence of Maine on our signature boat tours. Enjoy the serenity of coastal cruises while indulging in gourmet locally-sourced food and craft beverages. Our classic wooden vessels offer a truly authentic Maine experience for unforgettable memories.

Eager for an unparalleled experience? Book your private boat charters and coastal tours to navigate the beautiful waters of Casco Bay!

Dump out your bucket list.

This is the adventure you’ve been looking for..

Windjamming is, quite literally, like nothing else on Earth. By turns exhilarating, relaxing, surprising, and nurturing, it’s like no other vacation you’ve ever experienced.

Wake up to the quiet solitude of Maine’s coast, find renewal in the wind and sun, and surprise yourself as you help steer the ship. Aboard our vessels, with itineraries tossed to the wind, our guests find both a spark of adventure and time to reflect.

Is there a sailor in your soul?

Welcome to the Maine Windjammer Association – the largest fleet of traditional tall ships in the Americas. Our iconic windjammers offer multi-day, all-inclusive, sailing adventure cruises in one of the most acclaimed cruising grounds in the world.

When you sail aboard a Maine Windjammer Association vessel, you can be sure that your hosts hold themselves to the highest standards of safety and quality. As your captain and guide they will treat you to honest, heartfelt Maine hospitality and personalized attention.  Explore our fleet and offerings to find your perfect cruise.

The Windjamming Experience

Simply put, windjamming is about reconnecting with our essential enjoyment of life. It’s about gorgeous scenery, human connection, soul-nourishing meals, and taking time for both adventure and reflection. Our playground is the sparkling sea and the spruce-clad granite islands that rise from it.

Whether you join us for a three-night cruise or a week, we promise you a total escape from the ordinary. Be prepared to get closer than you ever have before to breathtaking wildlife like eagles, seals and porpoises, to visit some of North America’s most spectacular coastal scenery, charming villages and unspoiled islands, and to savor the freshest, fire-cooked Downeast fare. With only 16-31 guests on our ships, you’ll experience the kind of honest, heartfelt hospitality that keeps our guests coming back year after year.

Welcome to the only place in the world where schooners play in abundance. Where steady breezes, glittering bays, and literally thousands of islands make Penobscot Bay one of the most revered cruising grounds on earth.

On our small ship cruises, we have complete liberty to explore secret anchorages, remote fishing villages, and charming gallery towns. Schooners have been an intrinsic part of the Maine Coast for centuries, and there is something very special about rounding the point and arriving at anchorage under sail. Come touch this culturally distinct, pristine and physically breathtaking part of America.

Explore by Schedule

Use our cruise finder below to explore sailing options that fit your schedule. If your dates are flexible, or you just want to learn more, visit our fleet page and each vessel’s website. Reservations can be made directly with the Windjammer of your choice. Have fun exploring! Whichever vessel you choose, you are sure to have the sailing adventure of a lifetime.

Find My Trip

Leave your fancy clothes home for this low key, relaxing cruise. Experience quiet morning sunrises; the wind and sun on your face as you fly sailing across the water; beautiful scenery; and the most amazing (and never ending!) food. Maine lobster cooked right on the beach, ocean swims, and music night. This is a trip for making lifetime memories.

Stay in the Know

With our monthly newsletter, you’ll receive tips and hints from folks who have sailed as well as information about the best dining and attractions the area has to offer, special packages, windjammer history, events, and more!

You can request a mailed or digital packet of brochures, or you can find individual ships’ brochures under each listing on the fleet page.

You are using an outdated browser. Please upgrade your browser to improve your experience. We recommend Google Chrome.

TOURS STARTING ON 5/25 - WE'RE LOOKING FORWARD TO SEEING YOU!

Portland, Maine Boating Adventures

Explore casco bay in a custom-built rib boat where everyone gets a front-row seat see the crown jewel of maine on our exciting, adventure boat tours and excursions.

Your family doesn’t want to be crammed onto a crowded big boat tour of  Casco Bay. You want to have the time of your life zipping around Maine’s most postcard-perfect lighthouses, forts, wildlife,  and surrounding islands, with a small, select group and a front-row seat.

Only New England EcoAdventures blends education, excitement, and adventure into each Casco Bay adventure and offers first-class accommodations that let you see and sustain the stunning Southern Maine ecosystem.

We get there faster. We stay longer. And we go places other boat tours can’t reach—in a style they can’t match.

Upcoming Portland Boat Tour Adventures

• Most Popular!
• Map Marker Portland, Maine
• Hour Glass 1.5 hours
• Star Outline Seal watching , Lighthouse tour , Scenic cruise

Best of Casco Bay

Depart with us from bustling Portland Harbor as we tour one of Maine’s most picturesque boating destinations. Casco Bay is littered with islands, historic forts, wildlife, birds, and lighthouses in our unique 14-passenger RIB boat.

• Hour Glass 3 hours
• Star Outline Whale watching

Adventure Whale Watch – Portland

Experience the breathtaking beauty of the Atlantic Ocean on our whale-watching tour departing from Portland, Maine. Set sail from the historic harbor, where you’ll board a comfortable vessel equipped for a thrilling marine adventure.

• Hour Glass 2.5 hours
• Star Outline Oyster Farm Tour

Mere Point Oyster Farm Tour

Join us on a scenic ride of Casco Bay on our way to tour one of Maine’s premier oyster farms. Along the way we will cruise through some of Casco Bay’s less visited waters for great wildlife viewing before arriving at Mere Point Oyster Farm.

• Hour Glass 2.25 hours
• Star Outline Lighthouse tour

Portland’s Ultimate Lighthouse Tour

Experience the picturesque beauty of the Maine coastline with our exhilarating boat tour from Portland, Maine. This guided adventure will take you on a breathtaking journey along the rugged shoreline to view more lighthouses than any other tour in the state!

• Star Outline Scenic cruise

Small Group Adults-Only Sunset Adventure

Grab your favorite adult beverage and join us on an adults-only, intimate, sunset adventure that you won’t soon forget!

Portland, Maine and Casco Bay New England EcoAdventures let you learn, live, and love the Maine life like a local.

Our premium RIB boat takes you through Portland’s working waterfront where you’ll enjoy the islands, forts, lighthouses, vibrant seal colonies and seabirds.

Salty breezes and brilliant sunsets. Fresh, buttery lobster, blueberry pie, and craft beers. Shoals of playful dolphins and pods of majestic whales. Gentle cruises through scenic vistas and adrenaline-fueled, wind-whipped speedboat runs across sparkling waves.

We give you so many wonderful ways to truly experience the southern Maine lifestyle—and every guest gets a front-row, 360-degree view and in-depth insight into the wonders all around you.

Our Customers Rave About Us

The boat ride was so much fun and so much more intimate than a big boat. It can def. get a bit choppy at times but the seats are well cushioned which makes for a great adventure. Captain and staff are very nice and experienced. We saw some seals and 2 humpbacks which def. gave us a great show smacking their fins into the water. We would highly recommend this adventure. Regardless of what wildlife you will sight the boat ride on its own is worth the trip. Thx again.

It included stopping at an area to watch seals, a lighthouse and the history, seeing the Bush estate and their boat, and tons of thrills riding the waves! It was not rough as we thought and you don't get soaked; just a little bit of sea spray which was nice on a hot day. Captain Gary was knowledgeable and fun by throwing in humor now and then. We were glad for the little pockets in front of our seats to put our phones and jackets. We'll be back for another tour next summer and we really want to experience their Hampden Beach location.

We had a great time on our hour long scenic thrill ride! My husband and I took my dad as a belated Father’s Day gift (he loves a good rush) and we were not disappointed. The seats were neat. They were three vertical rows that you had to straddle. There was a handle bar in front of you. We felt safe and comfortable. It was a tremendous thrill. My only complaint is that I wish it lasted longer! Because of this, I’m excited to book another trip with them in the coming years, whether it’s the whale watch or the lighthouse tour. My family and I stay in Ogunquit nearly every year and this was a great new activity to try in the area! Highly recommend!! Thank you for a great time!

• Chevron down What To Expect
• A first-class adventure tour without any crowds
• A narrated ocean adventure
• Amazing wildlife and scenery
• Amazing photo opportunities
• Custom POD seats for maximum comfort
• 360 Degree views for everyone
• Educational face to face interactions
• A knowledgeable captain
• Chevron down What's Included
• Complimentary water
• Cooler with ice
• Motions sickness wristbands
• Chevron down What You Need to Bring
• Your camera (make sure it’s charged)
• Warm clothing (dressing in layers is always smart)
• Sturdy Footwear (flip flops are fine)
• Chevron down What Not to Bring
• We also recommend NOT wearing a dress
• Chevron down Important Information

After you Book your Tour

• You will be emailed a receipt immediately after you book. The receipt will contain all the necessary information that you will need.
• YOU DO NOT NEED A PHYSICAL TICKET.
• Please meet at the picnic tables outside of Fore Points Marina 20 minutes before your scheduled tour for check-in and wait for the first mate. Fore Points Marina is located at 1 Marina Way in Portland, Maine.
• There is very little storage aboard the boat – please no large bags or coolers.
• If you are taking a child, we have life jackets for children that are between 50lbs and 90lbs.
• If you are pregnant or have a history of back or neck problems, we recommend another tour.

Parking – Traffic can be very bad in Southern Maine in the Summer, please give yourself plenty of time. Parking options are below…

(1) We recommend using the Thames St. Parking Lot which is located directly in front of Fore Points Marina. The address to the lot is Eastern Promenade Trail, Portland, ME 04101. The rates are $5 an hour.

(2) There is also a parking garage on Thames St. It sits on the left before you get to the parking lot. It’s a little further of a walk but it’s sheltered. The rates are $5 an hour.

(3) Walking is always a great option! We’re just a 5 – minute walk from the hustle and bustle of Commercial St.

• Chevron down Additional Information

Browse our  Frequently Asked Questions for any additional information you may need or call us at 207-502-8040.

Guided Tours + Cruises

Sample the sights and sounds of the region.

When you visit the Greater Portland, Maine region you get a hands-on experience. Get up close and personal with our rocky coastline and sandy beaches. The region is your oyster and you can take on everything from kayak trips to lobstering tours to brews cruises.

Learn More On The Blog

Portland Discovery Land & Sea Tours

The perfect way to experience the coastal and inland areas of Greater Portland Maine.

Offering specialty food cruises, harbor tours, and private charters. Complimentary beer and wine with all cruises!

Visiting Maine and want to see whales, puffins, or the sights? Cap’n Fish is the way to experience Boothbay Harbor.

Portland's iconic ferry system with year-round ferry services, specialty cruises and private charters to the islands of Casco Bay.

Offer boat rentals and water taxi service & the perfect way to see and explore Casco Bay on a private charter.

Join us for a guided tour, pedicab ride, or explore the region at your own pace with a worksman bike rental.

Private sightseeing tours are available for couples and all size groups, from minivan to motor coach.

Highly interactive tours that will educate and entertain you all along the way. Foodie tours, history tours, and more!

Aboard the 74-foot traditional sailing vessel Frances for public day sailing or charter. Weekly special events.

Home to the best tours and activities in Maine. Authentic experiences led by locals. Your gateway to an unforgettable Maine.

Jump aboard New England Eco Adventure’s small, intimate excursions that blend adventure and education into one amazing trip.

Experience unforgettable storytelling—rich with heart, humor, and humanity—on a walking tour with Maine's top-rated guide!

Don't just see Portland- Discover it! Offer a wide variety of sightseeing and charter options by Land and Sea.

Operate a unique multimedia history tour aboard a Vintage Fire Engine. We explore the peninsula of Portland.

Refresh your spirit with a two-hour sail on Casco Bay and witness first-hand the forts, lighthouses, sea life and rugged coastline.

Hosted on a traditional lobster boat, Rugosa’s lobster tour offers the most exclusive, personal, and educational cruise in Kennebunkport.

For 20 years we have been offering cycling, walking, and multi-sport vacations in the most beautiful places in Maine.

Portland's #1 party boat! Join us on the water for a fully immersive way to experience Casco Bay and the islands, all while live bands set the soundtrack.

Explore the best of Maine with private sightseeing tours featuring chef prepared local cuisine and drinks. Unforgettable experiences await on our historic boats.

We offer a variety of fishing charters and tours for all skill levels, from beginners to seasoned anglers. Join us for a fishing or harbor tour!

A unique island experience within Fort Scammel on the private House Island in Casco Bay. Camp and tour the historic island!

A lobstering excursion for all ages while enjoying close-up views of historic lighthouses, civil war forts, and seals.

Maine’s first human-powered party boat. Book individual seats or the whole boat for a private tour of Portland.

All-inclusive tours providing guests a behind-the-scenes look at Maine’s breweries, distilleries, wineries, and more.

Land & sea adventures aboard a modern amphibious vehicle. A quacktastic historical tour of the Old Port and Harbor.

Scenic train ride along beautiful Casco Bay. Activities, historic railroad cars & exhibits.

Experience the Old Port's rich history since 1632. Over 50 historic stops! Memorable tour experiences not to miss!

Join our family owned and operated tour company for unforgettable explorations. Customized year-round tours.

Residents and guides, with enthusiasm and expertise in Portland’s history, food, drinks, art, music, and literature.

A day in the life of a lobsterman from pulling traps and setting traps to examining sea life and selling the catch.

Take a scenic trip aboard the vessel, Pamela B., with Seacoast Tours of Freeport in South Freeport.

We offer unique boat-based tours and experiences on the beautiful waters of Casco Bay!

City & 3 lighthouses Historical Sightseeing Tour with a REAL local, born & raised in Portland!

A family-owned and operated tour company sharing what we love about our charming city and the state of Maine.

• Mailboat Run

Hop on the Mailboat Run! The locals’ favorite way to experience Casco Bay – this true working boat carries passengers, mail and freight to Little Diamond, Great Diamond, Long, Cliff and Chebeague Islands. Year-round availability. Check out our blog for more information!

Narration provided with 10 or more cruise passengers.

Duration : 2.5-3.5 hrs. (times vary based upon route and cargo volume)            Runs : Daily

• Sunrise Run
• Diamond Pass Run
• 2024 Cruising Casco Bay Concert Series

CLOSED FOR 2023 ~ See you in 2024!

Maine Duck Tours

Duck Tours In Portland, Maine

Experience Portland by Land and Sea

Land & sea historical tour of portland and casco bay.

On our history and sightseeing tour of Portland, we’ll travel by land & by sea to explore many different points of interest.

Fun for all ages aboard a modern amphibious vehicle!

As you twist and turn through the Old Port aboard Maine’s famous, modern land and sea vehicle, or “Duck”, we’ll tell you about the legends and lore that have shaped Portland into one of the most historical cities in the nation.

Learn about places of interest to visit and many little known facts about the city that is nicknamed “The Phoenix.” Then, hold onto your tail feathers as we DRIVE into the waters of Casco Bay to view Portland’s working waterfront, Calendar Islands and marine wildlife.  This is Maine sightseeing at it’s best!

For all of our tour details, please visit our Portland Maine Tour page.

Top 10 Boat Tours & Water Sports in Portland!

We did it as a part of our Portland trip with small kids aged 3-7. We all enjoyed the tour of the city as well as the boat time as well. Dugan was very helpful in getting us oriented after the ride as well. Highly recommend this!

What a fun tour, we enjoyed our trip on land and water. Truly, it quacked us up! I would recommend this tour on the beginning of your stay in Portland, it will give you a nice overview of the area.

Dugan and captain Mike did an excellent job. Both were very professional. Dugan was a great host, he was very knowledgeable and friendly-I would highly recommend this tour if you are in Portland.

The Maine Duck Tours is a good way to oversee the city. You get taken on land and water so it is entertaining and fun!

ROCKY BOTTOM FISHERIES

Authentic lobster boat tours in portland, maine.

THIS IS A MAINE EXPERIENCE YOU DON’T WANT TO MISS!

Are you looking for a fun and memorable experience in Portland, Maine? Join us for a harbor tour aboard an authentic Maine fishing boat operated by a local fishing family .

You’ll feel like a true local fisherman as you explore Casco Bay! Whether you’d like to haul and set traps on a lobster tour , soak in the beauty of the Maine coast during a sunset tour, or arrange a private charter for your family or group, we’ve got your adventure covered.

OUR SERVICES

Lobster demos, sunset tours, private charters.

Celebrate your next gathering with a completely customizable private boat tour in Portland, Maine! Our vessels can host wedding parties, corporate outings, family gatherings, and more. Our crew will be your guides, DJs, and photographers as you explore scenic views and take photos at famous lighthouses in Portland.

Inquire today and create memories to last a lifetime!

FRESH MAINE SEAFOOD SHIPPED TO YOU!

Are you craving fresh seafood? We can ship a taste of Maine straight to your doorstep! Our fresh Maine lobsters and scallops are sourced by local fishermen from the pristine waters of Casco Bay in the Gulf of Maine, and can be shipped overnight anywhere in the country! Whether it’s a special occasion or a weeknight dinner, we can send fresh Maine seafood to your table.

Fresh Maine Scallops

Fresh scallops straight from the boat, hauled in by our hardworking fishermen! Our premium Maine scallops are hand-picked and expertly prepared, ready to be enjoyed. Whether you prefer delivery to your doorstep or convenient local pickup, our scallops are the best of the best!

Order Your Scallops now!

Live Maine Lobster

Do you miss the delicious taste of Maine lobster? We understand! Luckily, you don’t need to make a trip to Maine just to satisfy your lobster cravings. With a few clicks, you can enjoy fresh Maine Lobster delivered to your doorstep overnight. Whether you want to create your lobster rolls or host a classic Maine lobster dinner, you can do it all from the comfort of your home.

Place your order today!

READY TO SET SAIL? BOOK A BOAT TOUR IN PORTLAND, MAINE

Rockybottomfisheries.

Bird's Eye Maine

Giving you access to Maine's beautiful and hard to reach places

Private boat charters of Casco Bay

Affordable and reliable service in Casco Bay

Rent your own camper van and explore Maine

About Bird's Eye

Learn about all things Bird's Eye

" Having enjoyed sailing and motoring on the water for all my 96 years, including a stint in the US Navy, I found the cruise with Bird’s Eye Maine and the close up view of the busy Portland Harbor to be great fun! The cruise was well planned and executed by Captain Matt – it was a interesting and lovely boat ride " —  William, 96, Massachusetts

Portland's Party Boat

Baycycle cruise.

Bring your friends on Maine’s human-powered party boat!

• Calendar By Reservation Daily
• Clock 1.5 Hours

Maine BayCycle

Embark on an unforgettable adventure aboard Maine’s premier human-powered party boat – your pedal pub on the water! With 10 pedal stations and room for five additional guests, you have the option to reserve the entire boat for an exclusive tour of Portland, Maine, or simply book individual seats and mingle with fellow pedalers.

Bring along your favorite local brews and snacks, curate the perfect playlist, and prepare for a fantastic experience on the water. Complimentary coolers and ice are provided onboard for your convenience. Bask in the refreshing ocean breeze, soak up the idyllic summer weather, and keep a lookout for seals in the harbor! Our friendly captain ensures that your cycle boat tour of Casco Bay is nothing short of extraordinary.

Ideal for various occasions including wedding parties, bachelor/bachelorette celebrations, birthdays, family reunions, and team-building events, Maine BayCycle offers a truly unique experience.

Don’t miss out on the opportunity to embark on the ultimate booze cruise! Guaranteed fun awaits as you pedal your way around Portland.

Our Portland, Maine boat tours have a maximum of 15 seats, must be booked in advance, and are offered at 11 a.m. (weekends only), 1 p.m., 3 p.m., 5 p.m., and 7 p.m. from Bell Buoy Park, located between Casco Bay Lines and Flatbread Pizza on Commercial Street, Portland, Maine.

Five-Star Reviews on TripAdvisor!

We chartered the boat to kick out my sisters bachelorette weekend in town. It was so much fun. Than, our captain, was great is helping us take photos and letting us play whatever music on the boat. We saw seals right off the peir! It was an amazing start to the weekend everyone loved it.

I went on Maine BayCycle for the first time a few years ago when it first opened, and had the best experience, but last night sealed the deal for us. We were a total of 14 people, including our group of 7, and had the best time out on the ocean with our Captain. The experience is something you could never get from any other boat tour or water activity in Portlan

We had a large group of us, 12, and it was the best time of our whole trip! It was wild and the captain didn’t mind at all! We loved being able to bring our own drinks. We even asked if we could pay for another half hour so we could do it longer but unfortunately the time slots with the next group was too close. Best time ever!

We were very impressed and had a memorable evening peddling out in Casco Bay! Even though there were only 6 of us, we were able to comfortably peddle our way around. Bring your own drinks and music and enjoy the ride! Even better if you can catch good weather and a sunset. We will be back!

Dreams of duck boats foster a winning attitude among Red Sox’ three big prospects

PORTLAND, Maine — “What’s a duck boat?”

Earlier this year, Red Sox prospect Marcelo Mayer interrupted a conversation with assistant director of player development Chris Stasio and teammates Roman Anthony and Kyle Teel for clarification. The group was discussing the documentary “ Four Days In October ” and the remarkable experiences of championship teams in Boston.

But when Stasio mentioned the rides on duck boats through the city, Mayer and Anthony were perplexed. (Teel, who’d been on a Duck Tour during a family trip to Boston as a child, was not.)

As the players heard from Stasio about the parade of champions on amphibious vehicles, they became captivated.

Advertisement

“Every time when we see him, we’re like, ‘You ever been on a Duck Boat? Let’s go!’ ” said Mayer, who now has a duck boat as the wallpaper on his phone.

The prospects could have taken a Duck Tour during the Rookie Development Program in Boston in January. There also are duck boat tours in Portland, Maine.

But Mayer, Teel, and Anthony are resolute that they will not go on such a trip until they have earned one as World Series winners with the Red Sox. They regularly discuss their hopes of doing so.

“It became this ongoing joke that obviously isn’t much of a joke,” said Anthony. “We just pump each other up with it every day.”

“It’s freaking cool,” Teel said about taking a champion’s ride through the city. “That’s why we’re talking about it.”

In a way, of course, the whole line of conversation is preposterous. Anthony is still 19 — he turns 20 next week — and in his second full season of pro baseball. Teel, 21, is less than a year removed from being drafted out of the University of Virginia. Mayer, also 21, is in his third full pro season.

They’re all in Double A, with plenty of development in front of them before they’re even ready for the big leagues. Nonetheless, it is telling that the top three prospects in the Red Sox system are forging an identity built around team success.

“There’s expectations and there’s noise,” Anthony said. “As a group, when you go into it and just try to build off of each other each day and just try to go out there and win — and win where we are right now — it takes the pressure off. Not that there is any to begin with, but it takes that outside noise away.

“It’s a lot easier to play when you’re going out there and the goal is just to win. I think that’s why we’ve won a lot lately. And it’s fun, it’s really fun, regardless of where you are, to be a part of a team that’s winning.”

Teams don’t always appreciate that notion in the minors. Often, winning is treated as an afterthought for players striving to reach the big leagues, and rightly so.

In 2013, the Sox’ Low A full-season affiliate (then in Greenville) went 51-87. Yet it was a hugely successful year, given that Mookie Betts had an offensive breakthrough that redirected his path from relative obscurity to stardom.

A case can be made that the foundation of the 2018 World Series title was laid in no small part after Betts left Greenville, when he played — and won — with minor league teams that featured several future big league teammates.

Betts was part of a wave of prospects whose grouping elevated both individual and collective performances, playing for dominant teams in both High A and Double A. The success those young players experienced in the minors became a critical reference point.

Once in the big leagues, Betts, Travis Shaw, Brian Johnson, Jackie Bradley Jr., and others drew on shared experiences to reassure each other during times of struggle. Those dynamics contributed to a culture in which young, homegrown Red Sox players pushed and pulled each other to a title.

The Sox are hopeful that something similar might be at work in Portland, with results that could be felt for years to come.

“They want to win together. They want to do this together,” said Stasio. “I think that’s real. They’re not focused on poking their head in the big leagues or being an All-Star, accomplishing individual goals. Their goal is to win in Boston as a group and have a special experience with our group.”

Early in 2024, they’re doing that. Portland is 16-11, in first place in the Eastern League. Each win is celebrated with Teel — known to teammates as “DJ Base Monkey” — spinning decks.

Evaluators who have gone through Portland suggest the heralded trio is living up to its billing, even with offensive numbers that have been somewhat dampened by the typical arctic conditions at the start of a Portland season.

Mayer is hitting .276/.316/.448 with three homers, again hitting rockets. Teel, less than 50 games into his pro career, looks like a near-lock to be an everyday catcher based on his mature plate approach (.244/.361/.415) and defensive ability. Anthony has been crushing the ball, with results in May (.333/.467/.542) that have started to align with the quality of his at-bats.

“It’s a really [expletive] good team,” said a rival evaluator, noting that the talent base extends to include Nick Yorke, Wikelman Gonzalez, Eddinson Paulino, and others.

Day to day, the work by the prospects is specific and purposeful, whether it’s on swing decisions, defense, or attention to game details. But underlying those efforts is a collective ambition, one that is admittedly audacious.

“The city of Boston wants championships more than anything. We want them just as bad, maybe even more,” said Mayer. “We talk about it every single day — trying to win championships in Boston, bring championships to the city, bring joy to the fans.

“We see it as a challenge. Obviously if you want to win World Series, you’re going to have to deal with a lot of pressure. So in a way it’s good that we have it now, because it’s not going to go away.”

Alex Speier can be reached at [email protected] . Follow him @alexspeier .

Press Herald

Account Subscription: ACTIVE

Questions about your account? Our customer service team can be reached at [email protected] during business hours at (207) 791-6000 .

9 places to nosh on bagels in southern Maine

From old-school spots to foodie favorites, there's a 'hole' lot to try.

You are able to gift 5 more articles this month.

Anyone can access the link you share with no account required. Learn more .

With a Press Herald subscription, you can gift 5 articles each month.

It looks like you do not have any active subscriptions. To get one, go to the subscriptions page .

Loading....

Bread and bagels at The Works Cafe in downtown Portland. Photo by Aimsel Ponti

From New York-style boiled bagels to Montreal-inspired wood-fired ones, there’s lots of great bagels in southern Maine and several shops have the accolades to back that up.

In 2023, Bon Appetit named bagels from Rose Foods and Rover Bagel among the best in the country.

Two years before that,  Food & Wine Magazine put Rover, Forage and Scratch Baking Co. on its list of best bagels in the U.S.

Whether you like yours toasted with cream cheese or as the bread for your breakfast sandwich, you can find plenty of styles and flavors from Biddeford to Brunswick.

BEACH BAGELS

The offerings at Beach Bagels include a French toast and marble bagel, and the cream cheese menu comprises spreads like strawberry, olive and honey walnut. Along with breakfast sandwiches, Beach Bagels has hearty breakfast options like omelets and pancakes. Best of all, you’re steps away from a beach stroll. Just don’t let the seagulls steal your bagel. Advertisement

WHEN: 7 a.m. to 3 p.m. daily WHERE: 34 Old Orchard St., Old Orchard Beach. beachbagels.yolasite.com ______________

Dutchman’s opened in 2022 as a pop-up housed at Nomad pizza in Brunswick’s Fort Andross building. It’s since become a permanent fixture there and uses the pizzeria’s wood-fired ovens to bake its bagels. The hand-shaped, honey-boiled bagels come in plain, roasted garlic, poppy and a bagel-of-the-day flavor.

WHEN: 8 a.m. to 1 p.m. Thursday to Sunday WHERE: Fort Andross, 14 Maine St., Brunswick. dutchmans.me ______________

FORAGE MARKET

Making bagels at Forage Market involves a two-day aging process. The bagels are naturally leavened with wild yeast starter and baked next to a hardwood fire. There are usually five flavors available, including sesame and garlic. Breakfast sandwiches (including vegan options) are available. Forage also has a location in Lewiston. Advertisement

WHEN: 7 a.m. to 1 p.m. Monday to Friday, 8 a.m. to 1 p.m. Saturday and Sunday WHERE: 123 Washington Ave., Portland. foragemarket.com _____________

MISTER BAGEL

There are 10 or so Mister Bagel locations in Maine, including South Portland and Falmouth. It all began with the Portland location, which was the first bagel shop to open in Maine. The late Rick Hartglass started Mister Bagel in 1977, and it is still a family business. Music fans will appreciate the breakfast sandwich menu, which includes The David Bowie (bacon, egg and American cheese), the Jimmy Buffett (egg with roast beef and cheddar) and The Lady Gaga (avocado, salt and pepper, with or without egg).

WHEN: 6:30 a.m. to noon Monday to Friday, 7 a.m. to noon Saturday and Sunday WHERE: 599 Forest Ave., Portland. misterbagelforestave.com ______________

At Rose Foods, the menu varies depending on the day, but there are usually six to eight flavors available. For example, should you pop in on a Friday, you’ll find a poppy and onion bialy (a cousin of the bagel that is not boiled). Rose Foods also makes a number of bagel sandwiches, including the Classic Nova with Nova lox and the Classic Whitefish. Advertisement

WHEN: 7 a.m. to 2 p.m. daily WHERE: 428 Forest Ave., Portland. rosefoods.me

______________

ROVER BAGEL

At Rover Bagel, you’ll find wood-fired plain, poppy, sea salt, sesame and everything bagels available most of the time, and the spread game here is strong with cream cheese options like lemon-thyme-honey cream and chili-garlic.

WHEN: 7 a.m. to 1 p.m. Wednesday to Friday, 8 a.m. to 1 p.m. Saturday, 8 a.m. to noon Sunday WHERE: 10 West Point Lane Suite 10-204, Biddeford (Pepperell Mill). roverbagel.com

______________ Advertisement

SCRATCH BAKING CO.

You haven’t lived until you’ve experienced the line of devoted fans waiting for Scratch Baking Co. to open, especially on weekend mornings. Along with the popular Maine sea salt, plain and other everyday flavors, Scratch has a daily special bagel. There’s honeyed rosemary on Wednesday and jalapeno cheddar on Thursday. Scratch is also famous, at least to locals, for its P-Cheese spread. It’s a pimento cheese recipe made with cheddar, mayo, roasted red peppers and seasoning and was passed down to co-owner and head baker Allison Reid by her grandmother, Mern.

WHEN: 7 a.m. to 1 p.m. Wednesday to Saturday, 7 a.m. to noon Sunday WHERE: 416 Preble St., South Portland. scratchbakingco.com ___________

THE MAINE BAGEL

The Maine Bagel is a drive-thru with several breakfast and other kinds of sandwiches available. With a bagel list that features egg and bialy among the standards, the family-owned spot is the perfect place to stop on your way to Pine Point Beach. The Maine Bagel really shines with a dozen kinds of cream cheese spreads, including raisin-walnut, lox, strawberry, cranberry-nut and bacon-chive.

WHEN: 6:30 a.m. to 2 p.m. Tuesday to Friday, 7 a.m. to 1 p.m. Saturday. WHERE: 117 Route 1, Scarborough. themainebagel.com Advertisement

THE WORKS CAFE

The Works Cafe is an institution on the edge of the Portland’s Old Port. It opened in 1990 as Bagel Works before it changed its name in 2002. The original shop in this regional chain opened in Manchester, Vermont, in 1988, and there are 11 locations around New England, though just the one in Maine. Gone are the ’90s-era banana-walnut bagels and cold pizza cream cheese, but The Works Cafe is still a reliable place to grab a salt, multigrain or cinnamon raisin bagel, among others. The menu also has bowls, sandwiches and smoothies.

WHEN: 6 a.m. to 7 p.m. daily WHERE: 15 Temple St., Portland. workscafe.com

Success. Please wait for the page to reload. If the page does not reload within 5 seconds, please refresh the page.

Enter your email and password to access comments.

Forgot Password?

Don't have a commenting profile? Create one.

Hi, to comment on stories you must create a commenting profile . This profile is in addition to your subscription and website login. Already have a commenting profile? Login .

Invalid username/password.

Please check your email to confirm and complete your registration.

Create a commenting profile by providing an email address, password and display name. You will receive an email to complete the registration. Please note the display name will appear on screen when you participate.

Already registered? Log in to join the discussion.

Only subscribers are eligible to post comments. Please subscribe or login first for digital access. Here’s why .

Use the form below to reset your password. When you've submitted your account email, we will send an email with a reset code.

Send questions/comments to the editors.

Member Log In

Please enter your username and password below. Already a subscriber but don't have one? Click here .

Not a subscriber? Click here to see your options