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
(24 Ratings)
5 stars
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1 star
Judith_s
Jul 15, 2025
Wonderful sunset cruise.... - Wonderful sunset cruise. Great captain and crew! Beautiiful night, gorgeous sunset. Highly recommend
Review provided by Viator
Michael_f
Jun 22, 2025
Applejack Sail - Only to be prepared for cooler temps on the water with warmer clothes. Wonderful 2 hour sail. Captain Sean (sp) and first mate Brian (sp) absolutely engaging and so knowledgeable on the history of the area. We thoroughly enjoyed the sail!
Review provided by Viator
220macyh
Jun 22, 2025
Highly recommend - I cannot express how amazing this was! I took my mom out for a delayed Mother's Day gift. The process was easy and the views were spectacular- but we sat with Captain Sean and had the best time hearing all his stories. It was the most entertaining time and I want to do it again!
Review provided by Tripadvisor
Amy_h
Jun 6, 2025
Amazing Schooner adventure - The sunset Schooner sailboat trip was amazing! Our 3 guides were very knowledgeable and made our experience fun! The crew also gave our group a very informative safety lesson. They were friendly and included members of the group in raising the sails. The all outside seating added to the authentic sailing experience. It was a lovely relaxing sail. Members of my group purchased on board and enjoyed a glass of Preseco as the sun was beautifully setting. It was early June so wearing a light jacket was a must. We even spotted a harbor seal as we left the dock.
Review provided by Viator
Marshas680
May 30, 2025
Sunset sail out of Boothbay Harbor - Super relaxed sunset sail! Always wanted to sail and this 2 hour sunset sail was perfect! Katie and Brian were fun to chat with and we loved the experience!
Review provided by Tripadvisor
Peter_s
Oct 8, 2024
Very enjoyable evening - Very knowledgeable, friendly staff lovely evening. Calm waters. Enjoyed ourselves. Lovely scooter. Thanks
Review provided by Viator
Gregory_b
Sep 19, 2024
Great way to see the coast - Captain Kate was great !! Shaun was awesome too. Had a great time. We were told a lot about the area we were sailing through. Hit some fog but it brought a new fun adventure too. Highly recommend
Review provided by Viator
Marilee_m
Sep 1, 2024
What an experience! My... - What an experience! My best time ever on a boat. Gorgeous boat and lovely town but what made it unique was the Captain. What an incredible man with the most experience at sea you will ever meet. An experience to last a lifetime and I couldn’t recommend this more to anyone who will listen. A total must when in Booth Bay
Review provided by Viator
C7478qplindaf
Nov 15, 2024
Very small and quaint. Watch when you go. - Boothbay Harbor was beautiful but if you are visiting do it before Columbus Day weekend. Pretty much of the town closes up after Columbus Day. There were a few shops open and a few restaurants but it is a small town to begin with. I enjoyed it but….
Review provided by Tripadvisor
Kim_k
Sep 13, 2024
Cool ship - This was a very cool ship with a lot of history. I would have enjoyed hearing more about it . Beautiful evening and wonderful sail!
Review provided by Viator
From $60
up to 6 guests
1 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).