sailboat rides portland maine

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 ! 

Portland, Maine Historic Fort & Lighthouse Tours

• Most Popular!

Fort Tour on a Private Island

• User Kid Friendly
• Hour Glass 2 Hours

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.    

Sunset Lighthouse Harbor Cruise

• Hour Glass 1.5 Hours

 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.

• 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.

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.

Private Boat Tours and Island Adventures

Inquire about our tours.

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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

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!

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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.

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

Sailing daily from Fore Points Marina beginning in May 2024!

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 porpoise and seals. With Captain Nick or Captain Sam  as your seasoned guide, sit back and enjoy the view while you learn about our treasured Maine coast.

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.

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.

Private cruises individually tailored to exceed expectations. Include an experienced captain and deckhand.

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.

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.

NaviTour connects travelers to local tour guides, who offer an exciting range of unique trips!

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.

Cruise on a 85-ft, two-deck harbor cruiser, outfitted with a full galley and well-stocked bar.

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.

Leave ordinary at the dock and experience the beauty of Casco Bay like never before with individually tailored private charters aboard vintage Maine vessels!

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.

EARLY BIRD SPECIAL! BOOK IN MARCH AND GET 10% OFF. USE CODE: MARCH10.

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.

Maine Windjammer Cruises®

Maine Windjammer Cruises

Swift is a very special vessel designed in 1935 by Murray Peterson, a masterful naval architect famous for his coaster designs.  Originally intended as a luxury yacht, she was launched in 1983 after nearly twenty years of love and dedication to build her.

A diagram of Swift below decks and a more detailed description is on our Accommodations page.

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Copyright Maine Windjammer Cruises. Site by Adventure Advertising . All rights reserved.

THE 10 BEST Portland Boat Tours

Boat tours in portland.

• Gear Rentals
• Fishing Charters & Tours
• Nature & Wildlife Tours
• 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
• New England Eco Adventures - Portland
• Spring Point Ledge Lighthouse
• Fort Gorges
• Bug Light Park
• Casco Bay Custom Charters
• Ram Island Ledge Light
• Halfway Rock Lighthouse
• Portland Tall Ship Cruise Casco Bay
• Portland Breakwater Lighthouse
• Casco Bay Islands
• Two Lights State Park
• SeaPortland
• 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. Portland Tall Ship Cruise on Casco Bay

2. Guided RIB Boat Adventure of Casco Bay

3. Private Lighthouse Sightseeing Charter on a Vintage Lobster Boat

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

5. Private Sunset Charter on a Vintage Lobster Boat

6. Maine Whale Watching Tour in Portland

7. Portland Tall Ship Private Charter on Casco Bay

8. Seven Portland Lighthouses Tour

9. New England Fall Foliage Private Vintage Lobster Boat Cruise

10. Mere Point Oyster Farm Tour

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

Sea Kayak to an Island Tour in Casco Bay

Sunset Tour by Kayak on Sebago Lake Maine

Scenic Sebago Lake Historical Tour by Kayak

Fall Covered Bridge Kayak Tour, Southern Maine

What travelers are saying.

• Portland Tall Ship Cruise on Casco Bay
• Sunset Lighthouse Harbor Cruise from Portland's Old Port
• Seven Portland Lighthouses Tour
• Portland Maine Islands in Time Sunset Cruise
• Guided RIB Boat Adventure of Casco Bay
• Portland Discovery Land & Sea Tours
• Rocky Bottom Fisheries
• Lucky Catch Cruises
• Maine Duck Tours
• Wine Wise Events
• Sail Portland Maine
• Portland Schooner Co.
• Nautilus Sailing Company

Casco Bay Custom Charters

Private boat charters in portland, maine, search charters by group size.

Casco Bay Custom Charters offers 100% private charters for couples, families, and large groups up to 16 aboard classic Maine, wooden vessels. 

Small Groups (up to 6 guests)

aboard MONHEGAN

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Large Groups (7-16 guests)

aboard MARIE L

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

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

You’ve Finally Found Authentic Maine

Immerse yourself in the quintessential Maine experience with Casco Bay Custom Charters. Our tours blend the serene beauty of Maine’s coastline with the richness of locally sourced food and drinks, all while delivering unparalleled customer service. Aboard our exquisite wooden vessels, each journey is more than a cruise; it’s an authentic Maine adventure, steeped in tradition and natural wonder.

Enjoy an unforgettable boat charter from Portland, Maine! ⭐⭐⭐⭐⭐

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

Book your pedal boat booze cruise!

Now taking reservations for summer, 2024! 

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 unlike any other.

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!

• 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
• 2023 Cruising Casco Bay Concert Series