Boothbay Harbor Schooner: Maine Coastline Sailing

Embark on a 2-hour sail in Boothbay Harbor. Discover lighthouses, wildlife, and remote islands aboard the classic Schooner Eastwind.

Duration: 2 hours
Cancellation: 24 hours
Highlights
  • Boothbay Harbor Region - Our docks are centrally located in Boothbay Harbor’s historic waterfront. You are just steps away from 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
  • On-board restrooms
  • BYOB snacks and drinks (non-alcoholic)
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, 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
(179 Ratings)
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Aokuyiga
Aug 17, 2026
Great sailing day - We had a great sail with Captain Josh and Hallie. The boat is beautiful, and both Josh and Hallie made the informative and fun. Would highly recommend this trip.
Review provided by Tripadvisor
Dorothea_s
Aug 14, 2026
Beautiful way to spend an afternoon - This was a very relaxing way to spend an afternoon. Haley and Josh took very good care of us and were extremely knowledgeable of the area. It was a small group tour which made getting photos and talking with the crew easy on a beautiful schooner.
Review provided by Viator
Julia_p
Aug 13, 2026
Epic sailing trip - Such a wonderful experience. Captain and cocaptain were spectacular. Friendly and helpful. Great trip. We will do it again.
Review provided by Viator
Melissa_m
Aug 11, 2026
Fun time with knowledge... - Fun time with knowledge staff who share interesting info along the way. Perfect couple os hours spent on the water.
Review provided by Viator
Michael_c
Aug 11, 2026
We had a wonderful... - We had a wonderful afternoon sailing on the Eastwind. The well organized and friendly staff, comfortable and well-maintained ship and beautiful weather made for the perfect day.
Review provided by Viator
Rick_v
Aug 10, 2026
Relaxing and scenic. The... - Relaxing and scenic. The captain and first mate were upbeat and friendly . They answered all questions and thoroughly provided information about the area.
Review provided by Viator
Terry_f
Aug 6, 2026
It's a beautiful trip.... - It's a beautiful trip. The captain and his partner were very professional, polite and informative. We would definitely do this again.
Review provided by Viator
Rick_h
Jul 30, 2026
Great sailing adventure in Boothbay Harbor - Great cruise to see Boothbay Harbor. It was even a little cloudy and was still a great adventure. Learn a lot about sailing and the area. Make sure you find pier 4 for departure it’s a little tricky to find.
Review provided by Viator
Tracylfearon
Jul 29, 2026
Great way to spend an afternoon! - Matt (Capt) and Brian (mate) were awesome! Personable, professional, and informative. The boarding process was easy, with seats assigned so groups were able to be guaranteed a seats together. Drink menus were offered and service was swift. The weather was perfect and we were treated to seal and porpoise sightings. We didn’t go out as far as I thought we would, and I wish there was narration/information about what we were seeing. I don’t think either of those things detracted from the experience, though. I highly recommend this as great activity while visiting Maine!
Review provided by Viator
Alisa_o
Aug 6, 2026
August 2026 - If never sailing, great first time. But for other the vessel pretty much zigzags with harbor a few times. Did see the light house but not much else. The crew was great but overall disappointed in the experience since really did not travel anywhere.
Review provided by Viator