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 - Experience the stunning rugged coastline, adorned with lighthouses and seals, as the journey glides through the clear waters of Casco Bay.
  • Portland - Admire the beautiful skyline of Portland, Maine’s largest city, founded in 1786. Witness Portland’s bustling waterfront as fishing boats set sail and return to the wharves, which are…
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 enjoy the stunning rugged coastline, featuring lighthouses, seals, and seabirds.
(NOTE: This is NOT a narrated tour, but our crew is more than willing to answer any questions you may have about the sights).
People of all ages are welcome, whether you’re…

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
4.7
(199 Ratings)
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J
Aug 5, 2026
Would recommend - This was a very nice cruise. A beautiful boat with history. We got to ride on Bagheera, who used to be a racing yacht on the Great Lakes. Staff on the boat were very knowledgeable and happy to answer any questions. We had beautiful weather and a very calming time. To note, we were going to bring dinner with us but we're glad we didn't. The setup wouldn't suit such a decision but you'll have enough room to have some drinks and snacks. It was a tight fit with the amount of people on board, everyone had a spot to sit.
Review provided by Tripadvisor
Mariere3335ue
Aug 3, 2026
Authentic Adventures on the Water - We had an amazing time! Captain and his workers were so great and friendly. Definitely an A+ exeprience. I would totally do this again when I am back in town!!!
Review provided by Tripadvisor
Larry_l
Aug 2, 2026
Fun on the sea - Fantastic views, and a very helpful staff. It was great to see Portland from a different perspective, and get a closer look at some of the islands and lighthouses.
Review provided by Viator
Bianca_t
Jul 28, 2026
Great experience! We... - Great experience! We bright wine and snacks and were so glad we did! The captain was super nice and knowledgeable
Review provided by Viator
B6527vsgaryt
Jul 27, 2026
Wonderful Time Sailing! - My wife and I had a great time sailing. The crew was friendly and knowledgeable and the entire experience was fantastic.
Review provided by Tripadvisor
Sara_g
Jul 25, 2026
Do it! - This was an amazing experience!!! You spend a lot of time on the water and the views are unbeatable.
Review provided by Viator
Nicole_s
Jul 25, 2026
This was such a great... - This was such a great evening activity! The people operating the ship were very friendly and attentive, and I felt very safe the whole time! I went solo and ended up sitting next to a really awesome family- even invited me to dinner with them after! Was a wonderful night for a sail, and I’m so glad I went! 10/10 recommend!!
Review provided by Viator
Susanks7503im
Aug 2, 2026
A lovely way to spend an evening - It’s always a pleasure sailing, and we got a perfect evening. The crew were pleasant. I felt as though it could have been more engaging though not sure what I expected.
Review provided by Tripadvisor
Dennis_p
Aug 3, 2026
Seniors Beware - This is not a tour for seniors! There are no chairs or benches, no guard rails (there is a rope line, but you can’t lean on it that goes around most of the schooner. ) So you sit on the boat, but there are no handles to make you feel secure when the boat is pitching towards the water, which happens at every turn. There is no narrated interesting bits of information unless you are fortunate to sit near the captain. The ride basically goes near the Portland Lighthouse and then goes in circles for an hour. They tell you that you can bring food and alcoholic drinks, but it’s windy, you’re trying to not slip from wherever your sitting, there are no tables or cup holders, thus not too pleasant or really feasible. Also, it is very difficult to get up and move, so most people are just stuck where they are for two hours.
Review provided by Viator
Cathy_d
Jul 29, 2026
Fogged out! - The cruise was canceled because of heavy fog. It was not safe to cruise. They said our money would be refunded.
Review provided by Viator
From $77
up to 15 guests
1 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).