Windjammer Sail: Morning Cruise on Casco Bay

Join our two-hour Casco Bay Windjammer Sail for stunning views of lighthouses, seals, and historic sites. Perfect for all ages!

Duration: 2 hours
Cancellation: 24 hours
Highlights
  • Casco Bay - Discover the stunning inlet of Casco Bay located in the Gulf of Maine. While exploring the bay, enjoy the serene, refreshing waters as the breeze guides the journey.
  • Portland - Admire the breathtaking skyline of Portland, Maine’s largest city, founded in 1786. Witness Portland’s bustling waterfront as fishing vessels set sail and…
What's Included
  • 2 Hour Cruise
  • Life jackets for adults and children
  • Environmentally friendly marine composting toilet
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 morning Windjammer Sail on Casco Bay in Portland, Maine. This is an ideal opportunity 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…

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
5.0
(20 Ratings)
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Serena_c
Mar 2, 2026
Great Customer Service - I wasn’t able to make it however they were kind enough to call me and offer a different time slot which was highly appreciated
Review provided by Viator
Steven_c
Sep 20, 2025
Try this cruise-you won't be disappointed - We got to sail on a 101 year old schooner. The weather was great but we did not have enough wind to fill the sails. The sails were raised and anyone who was willing was able to join in. It was lovely to see the huge sails ready to push us along . Even if we could not have the wind take across the water-the crew was great. Heill was a great tour guide and so interesting. She answered all our questions and listened to our stories. We felt very safe having her and Jake crew the boat. Our captain was very friendly and made us know we were safe.
Review provided by Viator
Samuel
Sep 2, 2025
Excellent vibes - Friendly crew, great ride around the harbor on a beautiful working sailboat, and all around great vibes. This booking is def more of a ride than a tour— the crew do not have a pre-planned narrative describing the highlights of the bay— but the crew will answer any questions you have and were very friendly.
Review provided by Tripadvisor
Steve_w
Aug 27, 2025
Fun way to get out on the... - Fun way to get out on the water. Leisurely cruise. It isn’t narrated but the crew is happy to answer questions.
Review provided by Viator
Haley_s
Aug 13, 2025
Had such a great time on... - Had such a great time on the Casco Bay Morning Windjammer sail! The breeze was perfect, the views were beautiful, and the crew was super chill and friendly. It’s a really relaxing way to spend the morning in Portland. Oh, and definitely bring your own drinks and snacks if you want — makes it even better. Totally 5 stars from me!
Review provided by Viator
Gisela
Aug 10, 2025
Awesome time with Jacob and Erica! - Thanks to Karen, Jacob and Erica for a wonderful time this morning. We had the luck to have a private sail where they complied to our petitions! They were easy going and very professional! We strongly recommend it!
Review provided by Tripadvisor
R5081twaustind
Aug 3, 2025
Great views! - Went for a bachelor party and had a great time. Beautiful views of the bay and friendly/knowledgeable crew! Would go again!
Review provided by Tripadvisor
Stephen_d
Aug 2, 2025
I got engaged on the... - I got engaged on the timberwind, and the captain and crew were excellent. A great experience and wonderful memory.
Review provided by Viator
Jen_k
Jul 30, 2025
Windjammer cruise - It was nice and relaxing and we enjoyed talking with the crew. The boat was gorgeous and the crew was hardworking and efficient
Review provided by Viator
995belale
Jul 21, 2025
Relaxing sailing - Very relaxing sailing experience. The schooner was in great shape and the crew was excellent. Our captain was very friendly informative and shared lots of fun facts. Would recommend for those looking for a relaxing sailing experience.
Review provided by Tripadvisor
From $61
up to 15 guests
1 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).