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
4.6
(126 Ratings)
5 stars
4 stars
3 stars
2 stars
1 star
Michaelb18735
Oct 22, 2025
Wonderful trip - Fantastic time and the skipper and her family were excellent. Could not ask for a better time. The boat, the education, and the learning experience were great.
Review provided by Tripadvisor
Chitteroc
Oct 5, 2025
Beautiful ship, with a... - Beautiful ship, with a small number of passengers and a really fun crew. Our Captain Sarah and Mate Christine were excellent!
Review provided by Viator
Don_b
Oct 4, 2025
Smooth sailing - It was a windy fall day so make sure you bring a jacket under those circumstances otherwise dress accordingly
Review provided by Viator
Myra_s
Oct 3, 2025
Great Time - Amazing. Fun. Beautiful views. Great captain and mate. Such a good time with interactive hoisting the sails.
Review provided by Viator
Sherri_d
Oct 3, 2025
BEST afternoon ever!!! - The Captain and crew were AMAZING!! They were kind and funny….. very attentive to the needs of those sailing. They even had blankets! Reasonably priced…. BEAUTIFUL schooner!!!! Would STRONGLY recommend this!
Review provided by Viator
Jordandb3492sy
Oct 2, 2025
10/10 Sarah and Christina - We had the BEST time at the 10:30 2 hour sail with Captain Sarah and Christina! They had great stories, service, and recommendations on the area. Would highly recommend!
Review provided by Tripadvisor
Steve_d
Sep 30, 2025
Boothbay Harbor Schooner Sail - Outstanding sailing experience, we thoroughly enjoyed it! Captain and 1st mate were very enjoyable and engaging with everyone.
Review provided by Viator
P4424umjilla
Oct 13, 2025
Boothbay sail - Was a beautiful calm day. The crew were friendly, very approachable and even let people help hoist the sail. Only thing I would have liked was maybe some information about the area or folk tales or something like what sea life they encounter or fish in the area. Was actually hoping to see some sealife
Review provided by Tripadvisor
Heather_p
Sep 28, 2025
Sailboat ride - It was a nice sailboat ride out to Island and back. It was a cloudy cool day, no wildlife was seen. No narration on the boat..
Review provided by Viator
Rick_y
Oct 7, 2025
Crew was meh! - After sailing on the Eastwind no less than a dozen times in the last 14 years, this trip was our least favorite. There was a fairly good wind but we spent more time under power than we did under full sail. We spent a fair amount of time just dead in the water. Also, rather than continuing to sail closer to Ocean point and Ram Island, she cut the trip short, headed back toward Boothbay, then literally tacked back and forth, 3 or 4 times at the mouth of the harbor (presumably to fill up the balance of the 2 hours). The crew was friendly, but gave little information about the Harbor sights unless asked. The guests who were enjoying their first trip on Eastwind probably enjoyed it well enough, but for those who may have taken the trip in the past, it wasn’t up to the standards that we’ve seen.
Review provided by Viator