Boothbay Harbor Schooner: Maine Coastline Sailing

Experience Boothbay Harbor’s best sunset sail. Explore Maine’s coastline, lighthouses, and wildlife aboard the Schooner Eastwind. Book your unforgettable two-hour voyage today.

Duration: 2 hours
Cancellation: 24 hours
Highlights
  • Boothbay Harbor Region - Our docks are centrally located in the historic waterfront of Boothbay Harbor. Just steps away, you’ll find excellent inns, shops, restaurants, and various water activities. We collaborate with and support our waterfront community and are eager to guide you to all the wonderful experiences nearby.
What's Included
  • BYOB drinks and snacks (non-alcoholic)
  • On-board restrooms
What's Not Included
  • Gratuities
  • Alcoholic beverages
Additional Information

Sail away from it all on your two-hour voyage aboard Boothbay Harbor’s schooner to relax and see the Maine coastline. Lighthouses, fishing lobstermen, wildlife, and remote islands accessible only by boat dot the seascape.
Our goal is for you to experience the best two-hour classic sailing trip in the world. We have been working on this experience in…

Location
20 Commercial St
Commercial Street
In Boothbay Harbor, please look for the sign that says "Schooner Eastwind."
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings
4.7
(73 Ratings)
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1 star
Tammy
Aug 9, 2026
Beautiful day! Definitely worth it. - Ryan and Matt were great! Gave us some history and very friendly.
Review provided by Tripadvisor
Kerrisnnek
Jul 24, 2026
Sunset Sail - Had a wonderful time out on the Eastwind for their sunset cruise. We had a perfect night with the wind working in our favor. It was a nice and relaxing experience and highly recommend it instead of your typical larger sunset/sightseeing boat. Captain Justin and Hallie added to the experience both being very personable and knowledgeable.
Review provided by Tripadvisor
Navigator14695004364
Jul 24, 2026
Beautiful and relaxing - My family of 5 really enjoyed our sunset cruise. We were in capable hands with Captain Josh and first mate, Hallie. A beautiful and relaxing end to our trip. Highly recommend!
Review provided by Tripadvisor
Expedition428150
Jul 22, 2026
Fun family trip - You can make plans, but Mother Nature will always do what she wants. No sunset for the sunset tour, but it was still a wonderful experience. Even with the little bit of rain at the end of the excursion, I'd absolutely do it again.
Review provided by Tripadvisor
Amy_b
Jul 14, 2026
Sunset sail - Sunset sail was relaxing. A little overcast and breeze was a perfect change from the warm day. The crew was friendly and accommodating. Highly recommend!
Review provided by Viator
Kelli_h
Jun 26, 2026
Great sunset cruise - Captain Josh and Halle were amazing. The trip was informative about how a.sailboat works. They were super friendly
Review provided by Viator
Q48jxsharonp
Jun 3, 2026
Great experience with this crew - Great experience with a great crew…
Review provided by Tripadvisor
Mfbmbb
Oct 10, 2025
MB4 (NC) & mb (NY) Boothbay trip '25. - Sarah and Christina were great, highly recommend. Sarah and Christina were great, highly recommend. Sarah and Christina were great, highly recommend.
Review provided by Tripadvisor
B867pxlindag
Oct 6, 2025
Schooner Eastwind Sunset Sail - The Schooner Eastwind Sunset Sail was wonderful. A two hour sailing experience with a sunset near the end? Who could ask for more. Captain Katie and Marisen both handles the schooner with ease and grace. We lucked out with the weather this late in the season, but definitely dress in layers, it can get cold out there. They did have plenty of blankets for those that were chilly. Sunset was beautiful, my husband and I enjoyed it very much.
Review provided by Tripadvisor
O4029ldrichardr
May 23, 2026
It's worth it 👌 - Good trip, definitely worth the money. Didn't see much wildlife.
Review provided by Tripadvisor
From $60
up to 12 guests
1 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).