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
4.6
(55 Ratings)
5 stars
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1 star
Maureen_h
Sep 23, 2025
Wonderful, peaceful, and... - Wonderful, peaceful, and fun experience. It was so nice to get out on the water at sunset in a quiet way. The crew was great, the weather was perfect and the sunset was stunning.
Review provided by Viator
Lollyandy1
Sep 21, 2025
Relaxing and beautiful - Captain was very knowledgeable and made the trip interesting. Very relaxing and beautiful! Great way to see the coast and islands.
Review provided by Tripadvisor
Fearless713520
Sep 12, 2025
Perfect way to spend a beautiful evening! Awesome! - We had a wonderful time! The ship was beautiful and the crew was so friendly and knowledgeable. We shared a perfect evening! We had brought delicious lobster sandwiches, which we had purchased from a small, but wonderful lobster bar just minutes away from the boarding location. Drinks onboard were very reasonably priced and the entire experience was peaceful, fun and very special! Couldn't have asked for a more beautiful sunset or a more enjoyable evening! Thank you! We plan on going back next summer when our son comes to visit.
Review provided by Tripadvisor
Katherine_s
Sep 11, 2025
Very fun! They had a cash... - Very fun! They had a cash bar and an added bonus was that they had blankets on board in case you got cold. Would definitely recommend!
Review provided by Viator
Victoriaju1797sc
Sep 9, 2025
Sailing - Thank you for the wonderful adventure aboard the Eastwind Schooner. We enjoyed the sunset evening cruise. Highly recommended!
Review provided by Tripadvisor
991jenniferc
Sep 3, 2025
A good time with Captain Josh & Simeon - Captain Josh and Simeon took us around on the Eastwind Schooner for our sunset cruise. Drinks were plentiful if you wanted it. We brought lobster rolls to enjoy. A cannon was shot! We got'em! ;) Excellent views of sunset. Highly recommend!!! Fun times!!
Review provided by Tripadvisor
Ryan_m
Sep 2, 2025
Sara and Marrison were... - Sara and Marrison were excellent. It was the perfect weather, and the view of the sunset was serene.
Review provided by Viator
Joe
Aug 27, 2025
A fantastic cruise with a beautiful view. - We took the sunset cruise. It was great. The captain and his first mate were knowledgeable, attentive and entertaining. My family had a great time. I would wholeheartedly recommend this cruise to everyone I know.
Review provided by Tripadvisor
Kathleensn597fy
Jul 26, 2025
Sunset Sail - We brought our Vermont family on the East Wind sunset sail yesterday, 7/25/25 It was a very relaxing, enjoyable sailing and the crew, Captain Luke and first mate, Simeon were fun, professional and accommodating. The views of the Cuckholds, the shoreline and Boothbay were beautiful. We thoroughly enjoyed the sunset and peaceful sail. I would recommend this to both couples and families. As Mainers, they made us proud!
Review provided by Tripadvisor
Doug
Aug 22, 2025
Great sailing and Sunset…..one problem - First of all the crew did a great job in accommodating the passengers. The boat was very clean and shipshape. It was fun to see some of the passengers who raised the sails both children and adults teamed up. A great experience for all. The only negative we experienced and it was very unpleasant was the water that was pumping out of a small pvc tube . The water was flushing out to the port side thereby getting our shoes very wet. It would have been ok to get our shoes wet however it was toilet water coming out, it had a strong urine oder which was detected by all of us on the port side forward. This really upset the four of us that were affected by this. We had no problems paying the $60 per person to enjoying the experience, it was really sad that our experience was tainted by the discharge of toilet water. Shame on you!
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).