Casco Bay Windjammer Sail: Historic Schooner Cruise

Experience a two-hour Windjammer Sail on Casco Bay, Portland, Maine. Enjoy lighthouses, seals, and seabirds. Perfect for all ages. Bring your favorite wine or beer.

Duration: 2 hours
Cancellation: 24 hours
Highlights
  • Casco Bay - Enjoy the beauty of the rugged coastline, complete with lighthouses and seals, as we slip through the pristine waters of Casco Bay.
  • Portland - See the gorgeous skyline of Portland, Maine’s largest city which was established in 1786. Observe Portland’s working waterfront as fishing boats depart and return to the wharves that form…
What's Included
  • Environmentally friendly marine composting toilet
  • Life jackets for adults and children
  • 2 Hour Cruise
What's Not Included
  • Food and drink—But feel free to bring your own!
  • Gratuities
  • Group Narration - Our captain and crew are happy to answer questions about the harbor sights!
Additional Information

Join us for a delightful two-hour Windjammer Sail on Casco Bay in Portland, Maine, the ideal way to enjoy the stunning rugged coastline, featuring lighthouses, seals, and seabirds. Feel free to bring a meal, your favorite wine or beer, and unwind as you glide through the clear waters of Casco Bay. (Please note: This is not a narrated tour, but our crew…

Location
56 Commercial St
Commercial Street
Please check your reservation to see the meeting point for your cruise. We are at the end of the Maine State Pier. Walk past Gate 5 of the Casco Bay Ferry to the dock house on the right-hand side to receive your tickets.
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings
4.8
(91 Ratings)
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Alida_s
Jul 25, 2025
Wonderful Time! - Johnathan did a great job! He answered all our questions and made everyone feel comfortable! Great job!
Review provided by Viator
Walter_l
Jul 24, 2025
Great 2 hours on the... - Great 2 hours on the water. Captain and crew were knowledgeable and well spoken. Enjoyed history of ship.
Review provided by Viator
Cathyandrich
Jul 22, 2025
Outstanding - Friendly and professional. Knowledgeable. Felt very safe with Cpt. Jonathan and crew. Relaxing surrounded by beautiful scenery
Review provided by Tripadvisor
Jordan_m
Jul 14, 2025
Wonderful Time - Even though it was a very foggy night, the sun still peaked through and we really enjoyed the views on the sailboat. We made some friends along the way and really enjoyed talking to the crew! Highly recommend you do this awesome experience.
Review provided by Viator
Bensk5627lb
Jul 8, 2025
Amazing time! - We had an absolute great time with Noah, Lucas, and Kyle. The whole crew was very professional, but knew how to make it fun at the same time. They were very knowledgeable and talented at sailing into the Atlantic. I would highly recommend this experience. Thank you Noah and crew!!!
Review provided by Tripadvisor
Francis_s
Jul 3, 2025
Relaxing Sail - Good wind, great crew and captain. Bring a snack and drink or two with you and enjoy! We had a very nice experience.
Review provided by Viator
O1064hnangelas
Jul 1, 2025
Great views of Portland on a quick trip - Beautiful and relaxing sail around the coast! The crew was top notch, and they made it a wonderful experience. We brought our food and wine, and we had plenty of room to spread out. Amazing sights that gave us a taste of Maine on our first visit.
Review provided by Tripadvisor
Scottsj9505bq
Jul 25, 2025
Nice trip - This was a Nice leisurely sail. Bring a jacket or sweater as it can get chilly. No real dialogue to speak of letting you know what you are seeing. Strictly a sail. Left at 6 back at 8.
Review provided by Tripadvisor
Eric_h
Jun 26, 2025
Dull - No one can control the wind, but it was quiet and we moved very slowly unless the engine was turned on, which was used sparingly, and thus it was rather boring.
Review provided by Viator
663gerriep
Jul 25, 2025
Very disappointed - We booked a birthday sunset sail for 4 ppl. We tried a few yrs ago and was cancelled due to inclement weather. This sail launched, but in my opinion, should not have. There was a significant rain at check-in that continued for 2 hrs. We spent most of the sail below decks. We never felt unsafe, but this was certainly NOT the experience we wanted, or paid for! We left the boat completely soaked and uncomfortable. Very disappointed. I don't recall being offered an option to cancel or reschedule. We were relying on the boat crew to make the call. Never thought they would have sailed given the constant and sometimes heavy rain.
Review provided by Tripadvisor
From $75
up to 15 guests
1 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).