Windjammer Sail: Explore Casco Bay's Scenic Coastline
4.6
186 Ratings
Portland

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…

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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
4.6
(186 Ratings)
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Carrieml7291vm
Oct 27, 2025
Great time - It was chilly for most of it, but such a beautiful view! Saw a few seals while we were out and learned more about Portland. Great time
Review provided by Tripadvisor
Suzan_v
Oct 24, 2025
Great experience! - Wonderful experience with the captain and crew. Even got to help raise the sails. Lovely seeing Portland and the lighthouses by water!
Review provided by Viator
16stevend
Oct 19, 2025
Great cruise excursion for families! - We had a great time on this excursion. It was perfect weather that day. We did have to wait a little longer than expected to get on the boat, but it was so nice that day we really didn’t mind. The staff were all very friendly and accommodating. They were very personable and treated us well. We enjoyed the laid back leisurely nature of the experience. I would definitely recommend this excursion for anyone wanted to do something fun right of the cruise ship harbor.
Review provided by Tripadvisor
2016judy
Oct 18, 2025
Beautiful sail - Beautiful and peaceful respite from everything. This isn’t a sail where your are spieled dialogue which is a welcome change. Thoroughly recommend.
Review provided by Tripadvisor
Stephanie
Oct 16, 2025
Epic sailboat ride - The captain and crew were incredibly friendly and made the experience so much fun. The views were absolutely breathtaking, and I even had the chance to participate in raising the sail, which made the trip even more memorable.
Review provided by Tripadvisor
Diane_n
Oct 14, 2025
Great experience - This time of year dress warm! Very relaxing trip around the bay. Crew was knowledgeable about the area.
Review provided by Viator
K5859qrkarenp
Oct 13, 2025
First time on a Schooner - Best time ever! The Crew was very friendly and the Portland Harbor is beautiful! It was our first time on a Schooner and it didn’t disappoint!
Review provided by Tripadvisor
Elainebc525vw
Oct 20, 2025
Relaxing Trip on a Beautiful October Day - We went out on a beautiful day. The schooner was staffed with a skilled crew. We had a lovely view of the bay, and it was a glorious day. A relaxing trip was had!
Review provided by Tripadvisor
Sally_j
Oct 17, 2025
Not for everyone! - Not narrated, just a boat ride!! Expected them to talk about the surrounding area! It was like here is a boat ride down and back now tip us. No food or drink but welcome to bring your own.
Review provided by Viator
Pat_h
Oct 10, 2025
Not for kids!! - The crew was gracious and knowledgeable, but safety was lacking. It was an extremely windy day and they did not offer life jackets, which gave me pause for my six year old. Half way through, we caught a “rogue” wind gust which caused our boat to turn completely sideways and almost tip. One of the passengers went flying, breaking her arm and almost falling in. She was drenched and in distress, causing us to immediately return to shore. Had I not been holding tight onto my child, it would have been a terrifying situation. What was intended to be a two hour casual boat ride ended up being an extremely scary situation for my family. I would not recommend this for children whatsoever.
Review provided by Viator
Check Availability
From $67
From $67
up to 15 guests
1 - Adult
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Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).