Windjammer Sail: Explore Casco Bay's Scenic Coastline

Sail Casco Bay on a historic Maine schooner. Enjoy lighthouses, seals, and seabirds. Bring your favorite drink and relax on this unique adventure.

Duration: 2 hours
Cancellation: 24 hours
Highlights
  • Casco Bay - Experience the stunning rugged coastline, adorned with lighthouses and seals, as the journey glides through the clear waters of Casco Bay.
What's Included
  • Life jackets
What's Not Included
  • Food and Drink—But feel free to bring your own!
  • 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 about the sights).
Bring along a meal, your favorite wine or beer, and unwind as…

Location
56 Commercial St
Commercial Street
Please check your reservation to see the meeting point for your cruise. The Maine State Pier location: 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
4.7
(298 Ratings)
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1 star
Ruth
Aug 2, 2026
Delightful 2-hour sailing cruise in Casco Bay! - The captain and one woman crew were welcoming and impressive, providing an authentic sailing experience. They were happy to answer any questions, and invited guests to help hoist the sails.
Review provided by Tripadvisor
Wendy_h
Jul 29, 2026
Great sail! - Super friendly and very knowledgeable crew. Fog really rolled in and felt very safe. It was clear the Captain's had the experience and skill set to handle the fog. Thanks for a great sail even if the weather didn't cooperate so much.
Review provided by Viator
Rodneysu1955kk
Jul 28, 2026
Smooth and Cool - The staff were very professional and knowledgeable about at the history of the Bay. Length of tour was adequate for the area covered.
Review provided by Tripadvisor
Jilllw7438ez
Jul 28, 2026
Effortless - The trip was effortless from start to finish. It was a beautiful day and a nice way to explore the coast.
Review provided by Tripadvisor
Pamela_p
Jul 28, 2026
Windjammer - It was a lot of fun! The crew was friendly and knowledgeable and the sights lovely. We would do it again.
Review provided by Viator
Craig_b
Jul 27, 2026
FANTASTIC experience with... - FANTASTIC experience with a great crew. Highly recommended! Would definitely do this again in a heartbeat.
Review provided by Viator
Allenci1242hd
Jul 24, 2026
Great Crew - Excellent crew. Personable and made a point to chat with all voyagers. Captain Johnathan and his crew of Will and John were first rate. Also fun to be on such a historical vessel.
Review provided by Tripadvisor
Mikhail_m
Jul 23, 2026
Great experience, people... - Great experience, people were nice, captain was great!! Me and my wife had exceptional time onboard.
Review provided by Viator
R5559kbmarkc
Jul 27, 2026
Great - Portland Schooner Co. All aspects of sailing exceeded expectations
Review provided by Tripadvisor
Shorewalkernortheast
Jul 31, 2026
Overpriced and Underwhelmed - Maybe some have had better luck with other boat rides and customer service at this company, but our schooner ride was not in any way worth nearly $70 per person. The day we were there, I'd have paid just to get off the boat! This could have easily been improved if the captain had been attentive to the customer experience. It was hot and oppressively humid with no breeze, which is not the fault of the company. But after motoring away from the pier, the motor was turned off and since there was no breeze, we just sat there. I can see waiting a bit to see if the breeze picks up but when it doesn't, it's time to think of the customers' experience and pivot to another plan. There's no shade on the boat. So we inexplicably sat barely moving, in hot sun with no air for a full hour. Finally someone spoke up and politely asked the captain to turn on the motor. He conceded that he'd only turn on the motor "to keep the schedule" and finally did so. It apparently never occurred to him that it's not fun to pay nearly $70 each to sit still in the hot sun, that he should show us some sights and create a breeze. Customer experience is important; he may just be getting his two hour shift over with, but for some it's a rare chance to get out on the water! The second hour using the motor, we finally went around House Island, which if you know Casco Bay at all, is only about a mile and a half away from the Gateway pier, across the water. That is the entire distance we went in the two hour cruise. I contacted them after this trip but never heard back from anyone. There are NUMEROUS other companies offering cruises which are less expensive and you're guaranteed to actually see the sights, so next time I'll use one that consistently cares about its customers.
Review provided by Tripadvisor
From $69
up to 30 guests
1 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).