Schooner Applejack: Sunset Sail in Boothbay Harbor

Join Schooner Applejack’s sunset sail in Boothbay Harbor. Spot wildlife, explore islands, and enjoy 360-degree coastal views. Your Maine adventure starts here.

Duration: 2 hours
Cancellation: 24 hours
Highlights
  • Boothbay Harbor Region - Boothbay Harbor is a popular tourist and yachting destination. While here, enjoy studios and galleries featuring over 200 local artists. Known as “vacationland paradise.”
What's Included
  • On-board restrooms
  • BYOB snacks and drinks (non-alcoholic)
What's Not Included
  • Gratuities
  • Alcoholic beverages
Additional Information

Welcome Aboard Schooner Applejack in Boothbay Harbor; your Maine Vacation starts here! Join the Schooner crew for a sunset sail adventure on Boothbay Harbor’s oldest windjammer. Help hoist sails or take a turn at the wheel as we set a course out past Burnt Island Light, Squirrel Island, Ram Island Light and the outer islands of Boothbay. Keep a sharp…

Location
15 Wharf St
Wharf Street
Pier 1 in Boothbay Harbor
Cancellation Policy

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

Customer Ratings
4.9
(41 Ratings)
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Debrafr6475zw
Oct 5, 2025
Great first sailing experience - The whole trip was great. Luke was our captain and Chris Dena was the first mate. They were both wonderful and deserve a raise. 😊
Review provided by Tripadvisor
Ben
Sep 20, 2025
Applejack september sunset sail - Went early September 2025. Weather was perfect. Arrived 15 mins early. Awesome sailing trip. Sunset is the best. Slightly interactive. Beautiful old boat with lots of fun history.
Review provided by Tripadvisor
Lynn_d
Sep 20, 2025
Fun and relaxing experience - It was a fun and relaxing experience. My husband and I have never been sailing before. The captain and his crew were great from the start. Drinks are strong. Canyons and bubble wars were a real treat! The sunset was beautiful. Got some real candid shots. Incredible experience. Highly recommend this sailing trip. Lots if fun!
Review provided by Viator
Heidi_f
Sep 4, 2025
Best experience we had in Maine - We took the sunset cruise. The weather was awesome and the crew, Luke, was amazing. A must do when in Boothbay Harbor!
Review provided by Viator
637gaspert
Sep 2, 2025
Boothbay Harbor sail - As advertised, beautiful sunset cruise on old schooner around the harbor.we were actually on the sister boat Eastwind. hardly a breeze that night, very serene couple of hours . beer,,cocktails served by personable first mate, and captain.maybe 20 people aboard . Boothbay is a heavily touristed town and we were there over Labor Day wknd , in all in nice break from the very commercialized scene in town.
Review provided by Tripadvisor
Crystalcs959yl
Sep 1, 2025
Great experience - My husband and I were absolutely so relaxed. The Captain and Christina were knowledgeable, friendly and experienced. It put me in a space of trust where I could really enjoy the experience. I would readily recommend this experience to family and friends.
Review provided by Tripadvisor
Judy_k
Aug 25, 2025
Wonderful experience.... - Wonderful experience. Crew was awesome. Very enjoyable. Very relaxing , spectacular views. Highly recommend
Review provided by Viator
Avtrav2010
Aug 19, 2025
Fantastic Family Experience - Had an AMAZING time on our sunset sail! Cap’n Josh and Brian were fantastic, provided so much interesting info, ensured that our sail was comfortable and enjoyable, and engaged our son in helping out too! We will definitely come back and do this again.
Review provided by Tripadvisor
Kim_m
Aug 15, 2025
Our family had a... - Our family had a wonderful experience. The waters were very calm and the sunset was beautiful. The crew was excellent.
Review provided by Viator
Nomad09406931893
Oct 2, 2025
Beautiful schooner, peaceful sail. Experienced crew but not informative about the history or geography of the area. - Beautiful schooner and peaceful sail. Crew was pleasant & experienced but not informative about history or geography of the area.
Review provided by Tripadvisor