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, an ideal way to admire the stunning rugged coastline, featuring lighthouses, seals, and seabirds.
(Note: This is not a narrated tour, but our crew is more than happy to answer any questions you may have about the sights).
People of all ages are welcome, whether you’re nine…

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
(131 Ratings)
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Katie_s
Oct 8, 2025
The crew was great, its a... - The crew was great, its a great sailing experience on beautifully restored sailboats. Sunset cruise was beautiful. Be sure to wear layers.
Review provided by Viator
Jayse7814hf
Oct 7, 2025
Top Notch Experience! - Amazing experience! We were on a boat with Captain Noah who was equally knowledgeable and fun. Bring a drink and lean into the heel! I would definitely do it again.
Review provided by Tripadvisor
899sherylc
Oct 4, 2025
Beautiful sunset cruise - Absolutely gorgeous sunset cruise ride through the bay. So relaxing and the staff were so friendly and knowledgeable.
Review provided by Tripadvisor
Dan_p
Oct 4, 2025
Wonderful experience! ... - Wonderful experience! Great views and crew! The sailboat was amazing and overall I'd recommend to anyone in the area.
Review provided by Viator
Emily_b
Oct 4, 2025
Great Afternoon activity! - The experience was exactly as described. We brought wine and cups. Crew was friendly and blankets were provided.
Review provided by Viator
Kyle_r
Sep 29, 2025
Sail Away - Beautiful night to be sailing. Crew and captain were a joy ! Would do it again! Saw several lighthouses.
Review provided by Viator
Kaitlyn_v
Sep 28, 2025
Sunset Views were stunning. - Chill and beautiful experience with fun and welcoming guides. The sunset cruise was a perfect anniversary celebration.
Review provided by Viator
Meg_m
Oct 10, 2025
Sunset cruise - This was a lovely experience. Definitely wear layers although they have plenty of blankets. We had beautiful blue skies and saw the sun set. The only negative was that they must have overbooked the trip and there wasn’t enough space for everyone to sit. Otherwise great experience. If you’re driving there is a parking garage next to the meeting place. Be sure to get there early as it fills up quickly.
Review provided by Viator
Kenst973uw
Oct 10, 2025
Great crew and ship. - The crew was exceptionally kind helpful and cordial. The schooner was absolutely amazing and beautiful. Remember how cold and windy it can be on the water and dress accordingly.
Review provided by Tripadvisor
B9283crmaryd
Oct 4, 2025
Wouldn’t recommend if you want a sunset cruise. - Family of 4 adults on the sunset cruise and we were all left puzzled. We have done sunset cruises before and actually enjoyed watching the sun set. This tour just turned a big circle in the bay which was pleasant enough if that was all you are looking for in a sunset cruise. The masts were down about 20-25 minutes before sunset and we were off the boat well before sunset. The photo advertised is far from accurate.
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).