Afternoon Windjammer Cruise Along the Coast of Portland Maine
Overview
Available languages
2 hours
Mobile ticket
Sail with us for a two-hour Windjammer Sail on Casco Bay in Portland, Maine — the perfect way to experience the beauty of the rugged coastline, complete with lighthouses, seals, and seabirds
(NOTE: This is NOT a narrated tour, but our crew is happy to answer any questions you have about the sites).
Pack a meal, bring your favorite wine or beer, and sit back and relax as you slip through the pristine waters of Casco Bay. All ages are welcome! Whether you are nine years old or 99, sailing aboard one of our Maine historic schooners is a unique adventure. All of our wooden windjammers were built in Maine and three are listed on the National Register of Historic Places.
Additional Info
Infants and small children can ride in a pram or stroller
Public transportation options are available nearby
Specialized infant seats are available
Suitable for all physical fitness levels
What To Expect
Casco Bay
Enjoy the beauty of the rugged coastline, complete with lighthouses and seals, as we slip through the pristine waters of Casco Bay.
Options
Afternoon Windjammer Cruise Along the Coast of Portland Maine
Duration: 2 hours
What‘s Included
Life jackets
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!
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
Reviews
193 reviews
Total reviews and rating from Viator & Tripadvisor
Yes, but...
618kathim,Jun 11, 2026
- Review from Tripadvisor
4.00Loved the ride but wished they would identify what we're seeing and act more like tour guides than just drivers. Very casual; captain spoke with people seated near him, but we couldn't hear. Big mixup and they took off without us, just 4 minutes late (due to ship immigration), (meaning they actually left early, by the time it took to maneuver out of docking spot, etc.). They let us on the next cruise, but we had to wait 2.5 hours. We'd even called that morning and left a message about the immigration process making us late, but they never listened to messages. We'd still recommend the cruise, as it is beautiful and we're giving grace as it was only the 1st and 2nd cruise of the season, so they obviously had some bugs to work out and very young employees.
Sail in the sun
Cheryl C,Jun 9, 2026
- Review from Tripadvisor
5.00Beautiful cruise on a sunny day with great crew
The Best Part of Our Long Weekend in Portland
6billd,Jun 9, 2026
- Review from Tripadvisor
5.00Sailing Portland Bay in a windjammer was the ultimate experience for our 3-day visit to Portland. Boarding was easy, but seating was pretty close on the deck structures. There were about 55 people aboard, plus 3 crew. We sailed for about 2 hours back and forth across the harbor bay. The wind was up, but the waves were easy, and the sun was warm. (Nobody got seasick. Yay!) Seeing Portland and the many islands from a sailing vessel really gave us a feel for the historical context of the this lovely area. The romance of sailing on the beautiful vessel inspire one fella to propose to his girl while we were mid-cruise.
Wonderful sailing experience ⛵️
O3912XQamandac,Jun 6, 2026
- Review from Tripadvisor
5.00The pier location was difficult to locate near the cruise terminal & I did have to call to make sure we were in the correct spot but everything else was completely amazing! Our captain, Noah and Deckhand, Courtney were a lot of fun and very knowledgeable. Would do this again!
Smooth sailing
kirk w,Jun 5, 2026
- Review from Viator
5.00Pleasant way to spend a couple of hours to see the islands. Easy to find. Friendly crew. Good sites to see along the way.
Great time
carriemL7291VM,Oct 27, 2025
- Review from Tripadvisor
5.00It 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
Great experience!
Suzan V,Oct 24, 2025
- Review from Viator
5.00Wonderful experience with the captain and crew. Even got to help raise the sails. Lovely seeing Portland and the lighthouses by water!
Relaxing Trip on a Beautiful October Day
elainebC525VW,Oct 20, 2025
- Review from Tripadvisor
4.00We 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!
Great cruise excursion for families!
16stevend,Oct 19, 2025
- Review from Tripadvisor
5.00We 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.
Beautiful sail
2016Judy,Oct 18, 2025
- Review from Tripadvisor
5.00Beautiful and peaceful respite from everything. This isn’t a sail where your are spieled dialogue which is a welcome change. Thoroughly recommend.
Related Experiences
Operated by Portland Schooner Co.