1. Sail Portland Maine

    sailboat tours portland maine

  2. Schooner Sailing Portland Maine

    sailboat tours portland maine

  3. Portland, Maine Boat Tours, Sails, and Public & Private Charters

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  4. Historical Sail Boat Used by Tourist for Sailing Tour in the Bay of

    sailboat tours portland maine

  5. 2024 Guide To The BEST Maine Sailing Tours

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  6. Photo Gallery

    sailboat tours portland maine


  1. Whitewater Rafting in Maine

  2. William Bligh: Paceship East Wind: The Grand Tour!

  3. Boat to walking tour teaches about value of island ecosystems in Maine

  4. Ships, Sailboats On Display At Maine Boatbuilders Show

  5. Bought a sailboat with ZERO sailing experience

  6. Experience Portland Maine


  1. Sail

    Windjammer Sails. Sail with us for a two-hour Windjammer Sail on Casco Bay in Portland, Maine — the perfect way to experience the beauty of the rugged coastline, complete with lighthouses, seals, and seabirds. Pack a meal, bring your favorite wine or beer, and sit back and relax as you slip through the pristine waters of Casco Bay.

  2. Portland, Maine Boat Tours, Sails, and Public & Private Charters

    Every day we offer two-hour public or private charters that might have you cruising past lighthouses, historic forts, and seals swimming in the harbor of Casco Bay. At Sail Portland Maine we offer intimate, crowd-free, professionally-captained and crewed excursions aboard our vessels, the Eleanor Hawkes or the Calista Ann.

  3. Sailing Tours Maine

    Explore Portland, Maine, with our exclusive tours that offer unique insights into local culture, cuisine, and nature unlike anywhere else. Professional Crew. Sail with confidence knowing that our skilled and experienced crew prioritizes your safety, comfort, and enjoyment on every voyage. BYOB and Snacks!

  4. Portland Maine Sailboat Adventures

    A sailboat charter business offering scenic and historic tours. Book your adventure! Explore the beauty of Maine from the sea. Sail past lighthouses, picturesque islands, lobster boats, and historic Fort Gorges. ... ©2023 Portland Maine Sailboat Adventures. Contact Alex at [email protected]. Day Sail. Every day, June through ...

  5. Nautilus Sailing Company

    Book a sailing adventure for a day trip, sunset cruise or your own private charter in Portland, Maine! DAY SAILS &. PRIVATE CHARTERS. 11:00 AM - 1:00 PM | Morning Sail. 3:00 PM - 5:00 PM | Afternoon Sail. $80 per Person | $450 Private Charter. Hop on one of our 2-hour morning or afternoon sails to explore Maine's diverse and scenic Portland ...

  6. THE 10 BEST Portland Boat Rides & Cruises

    per adult. 24. Sunrise/Sunset Boat Tour, Portland's Casco Bay, Bird's Eye Maine. Sunset Cruises. 2 hours. Embark on an unforgettable Sunrise or Sunset boat tour of Casco Bay in Portland, Maine, where nature, history, and natural…. Free cancellation. from. $390.

  7. SeaPortland

    Maine Island Rum Tasting and Boat Tour. Embark on a one-of-a-kind rum tasting adventure with Sea Portland and Three of Strong Spirits. Cruise Casco Bay to House Island aboard the Elizabeth Grace for a 90-min journey through Portland' Maine's candid history with prohibition and rum. Learn More.

  8. Portland Schooner Co.

    Cruises + Tours; Indoor Fun; Kid-Friendly; Museums + Historic Sites; Outdoor Activities; Shop; ... Portland, Maine 04101 . P. (207) 766-2500 . T. (877) 246-6637 ... sailing aboard our Maine schooners is a unique adventure. Two-hour day sails, lighthouse cruises, special events and private charters are available.

  9. Reserve Your Boat Cruise in Portland, Maine

    Enjoy a two-hour public or private boat cruise on the Casco Bay with Sail Portland Maine. Choose from our sailboat, Eleanor Hawkes, or our motor yacht, Calista Ann, and experience the beauty and history of Portland, Maine.


    6:00 - 8:00 PM | Sunset Sail. Fall Hours May Vary. $95 per Person | $550 Private Charter 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.

  11. Casco Bay Custom Charters

    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.

  12. Portland: Schooner Tall Ship Cruise on Casco Bay

    Set sail on a two-hour cruise from Portland along the rugged coast of Casco Bay. Pack a meal and your favorite wine or beer, and sit back and relax as you slip through the peaceful waters of Maine. Enjoy views of lighthouses, seals, and other coastal wildlife aboard a famous schooner tall ship. Join the crew to hoist the sails or take a turn at ...

  13. 2024 Guide To The BEST Maine Sailing Tours

    Portland & Casco Bay Sailing Tours Portland Schooner Co. Portland. 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.

  14. Portland: Schooner Tall Ship Cruise On Casco Bay

    Enjoy a 2-hour Portland Schooner Tall Ship Cruise on Casco Bay for just over $100 per person. Free cancellation up to 24 hours before departure for stress-free planning. Encounter seals, seabirds, and dolphins while sailing on a famous schooner tall ship. Maine State Pier is the meeting point for a memorable journey with breathtaking views of ...

  15. Portland Maine Traditional Windjammer Sailing Tour 2024

    See a new vantage on Portland and the Maine coast—and enjoy a relaxing excursion out on the water—on this sailing tour. Make your own way to the Maine State Pier, and hop aboard a traditional, Maine-built windjammer. Once you set sail, soak up the sea breezes, look out for seals, and even take a turn at hoisting the sails or behind the ship's wheel.

  16. Kennebunkport & Portland Maine Boat Tours

    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. Book Now. Learn More. From $89.00. Portland, Maine. 2.25 hours.

  17. Portland, Maine Boating Adventures

    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! Book Now. Learn More. From$149.

  18. Portland ME Boat Tours

    The Scenic Route Maine Tours. A family-owned and operated tour company sharing what we love about our charming city and the state of Maine. Kayak trips, brew tours, foodie tours and seal cruises; cruises and tours are the perfect way to experience the coastal and inland areas of Portland Maine.

  19. Portland Maine Cruises, Casco Bay Tours and Boat Rides

    56 Commercial Street, Portland, Maine 04101 Phone: (207) 774-7871 Fax: (207) 774-7875 Email: moc.s 1721182880 enily 1721182880 abocs 1721182880 ac@of 1721182880 ni 1721182880 Year-round ferry services, scenic cruises and boat tours from Portland, Maine to the islands of Casco Bay, including: Peaks, Little Diamond, Great Diamond, Diamond Cove ...

  20. Portland Discovery

    MOST POPULAR LAND TOUR! 1 hour and 45 minutes. April 27 - October 27. Adult: $45 • Children: $30. Enjoy a 1 hour and 45 minutes, fully narrated trolley tour of scenic and historic Portland and visit Maine's oldest lighthouse, Portland Head Light for a 30 minutes stop. The childhood home of Henry Wadsworth Longfellow, the Victoria Mansion ...

  21. The BEST Portland, Maine Cruises & boat tours 2024

    The best Portland, Maine Cruises & boat tours are: Portland: Sightseeing Cruise to Portland Head Light. Portland: Casco Bay Sunset and Lighthouse Cruise. Portland: Schooner Tall Ship Cruise on Casco Bay. Portland: Sunset Lighthouse Cruise in Casco Bay with Drinks.

  22. Maine Duck Tours

    For all of our tour details, please visit our Portland Maine Tour page. Top 10 Boat Tours & Water Sports in Portland! Family fun! 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.

  23. Private Lighthouse Sightseeing Charter on a Vintage Lobster Boat

    100% PRIVATE TOUR! Step aboard a vintage Maine Lobster Boat for a private, 2-hour lighthouse viewing & sightseeing charter. Leave the crowds behind as we tour the islands of Casco Bay and pass by 4 lighthouses, historic 19th century forts, and the scenic Maine Coast. Charters depart from Portland's Old Port.

  24. Boat Tours Portland Maine FAQs

    Book Your Casco Bay Boat Tour in Portland, Maine. Come cruise aboard the Eleanor Hawkes, a traditional friendship sloop, or our newly acquired cocktail cruiser, the Calista Ann, and enjoy a trip of a lifetime on the most unique boat tours Portland Maine has to offer. Book your charter with Sail Portland Maine today!

  25. Cruise Return to Portland and Livestream

    The TSSOM will arrive in Portland, Maine, on July 16, 2024, at the Portland Ocean Terminal. This is the final stop of the 2024 Summer Training Cruise, and students will begin disembarking on Thursday, July 18, starting at 12:00. Please join us in welcoming back everyone aboard after a successful voyage, either in person or via the livestream.

  26. GLEAM Sailing to partner with Casco Bay Custom Charters to offer

    Casco Bay Custom Charters, Portland's premiere private boat charter company, is excited to announce a partnership with GLEAM Sailing from Newport, Rhode Bangor, ME 84

  27. Sports Digest: Falmouth native Chris Poole claims significant sailing win

    He finished third in the Tour de France in 2021 and won the 2019 Giro d'Italia. British rider Simon Yates was second, 37 seconds behind Carapaz. Pogacar slightly increased his lead over Jonas ...