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Boothbay Harbor Schooner: Maine Coastline Sailing
4.6
87 Ratings
Boothbay Harbor
Embark on a 2-hour sail in Boothbay Harbor. Discover lighthouses, wildlife, and remote islands aboard the classic Schooner Eastwind.
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.
- 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)
- On-board restrooms
- BYOB snacks and drinks (non-alcoholic)
What's Not Included
- Gratuities
- Alcoholic beverages
- 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…
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 Boothbay Harbor for almost 50 years, have a strong local following, and have been featured in national, best-selling publications.
We have the best sailing vessel for exploring Boothbay Harbor. We use an onboard engine to get us to the sailing grounds quickly. The size of our vessel is perfect for exploring all the areas of our rocky harbor to see life along the Maine coast. There are no obstructions on our deck other than the masts, so you always have a full 360-degree view from every seating position.
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.
For a full refund, cancel at least 24 hours before the scheduled departure time.
Customer Ratings
4.6
(87 Ratings)
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1 star
William_l
Jul 8, 2025
Family Celebration - The 2 hour voyage took us to the outer harbor. It was extremely relaxing and interesting to see the area from a totally different perspective. Lots of small islands, incredible houses and other amazing vessels . We traveled with three young children, ages 4,10 and 12, as well as 2 seniors and 6 adults. Very family friendly. The crew was incredibly knowledgeable and easy to engage in conversation. Drinks were available. Everyone throughly enjoyed their time on the schooner. We were reluctant to purchase tickets in advance of weather reports but with Viator’s flexible cancellation policy, which we used to cancel one ticket, there was no risk. A wonderful excursion for a reasonable cost which we would highly recommend.
Review provided by Viator
Meganfmantey
Jul 7, 2025
Family Friendly - Great way to explore Boothbay Harbor and see some of the coast of Maine. The Eastwind crew was professional, knowledgeable, and hospitable. It was a great addition to our time at the midcoast and our out of town visitors enjoyed exploring via a schooner. Definitely recommend!
Review provided by Tripadvisor
Donna
Jul 4, 2025
GREAT COUPLE OF HOURS - A group of 4 friends/family went on the 12:30 sailing yesterday. It was warm 78°, sun was shining, water was beautiful. The crew of Christina, Simeon and Josh were fun, interesting and knowledgeable. E we got back to shore with about 5 minutes to spare before the skies opened up and the hard rain began. It was a good day
Review provided by Tripadvisor
Christineka4745es
Jun 23, 2025
Boothbay Harbor Sail - It was a beautiful and a great trip. Josh the captain and Christina were the best. I help pull up the sails with Christina and Josh answered all our questions. I would definitely do this with this company again.
Review provided by Tripadvisor
Guide66970155213
Jun 22, 2025
Sailing with Captain Josh & Christina! Highlight of our trip! - We had such a wonderful time! My daughter loved getting hands-on and helping with the ropes, and Christina was so generous with her time—sharing stories and chatting with us about her sailing experience. Captain Josh was fantastic, answering all our questions and entertaining us pointing out highlights of Boothbay Harbor with great stories. The crew was both professional and personable. I felt completely confident in their care. Don’t miss this when you visit and ask for Captain Josh and Christina!
Review provided by Tripadvisor
Eileen
Jun 1, 2025
Sunset Sail - Wonderful crew!!
Marison answered all our questions about the area, lobster fishing and sailing while CA Luke and Josh navigated the harbor.
Highly recommend.
Just remember to tuck a hat in your pocket and dress in layers regardless of how warm it was on land😉
Review provided by Tripadvisor
Northstar36728177652
Oct 5, 2024
Beautiful Sail. - A beautiful day to sail and see beautiful scenery. Crew were friendly and attentive. Enough commentary to make it interesting without disrupting the ambience. Highly recommend
Review provided by Tripadvisor
Paulss9133lq
Jun 30, 2025
The schooner Eastwind 2: hardly sailing. - It was a nice, leisurely tour of the harbor, but the captain, Josh, was more interested in palaver than sailing. I never saw a sailboat go from close hauled (heading as close as possible towards the wind) to a broad reach (heading away from the wind) without adjusting sails. Josh did not bother. Every boat in the harbor was flying a jib, but our jib was not raised. His crew said it was because "we didn't need it." She had only about a year and a half sailing experience in Florida and was really more attuned to selling drinks. If you want to sit on a boat and see Boothbay Harbor for $50 per person, why not go? If you want to enjoy a little sailing on a schooner, don't bother.
Review provided by Tripadvisor
Bethany
Jun 14, 2025
Unexpected rudeness - We had a truly lovely evening aboard the ship celebrating our 30th wedding anniversary, thanks to the fantastic crew. The onboard staff went above and beyond to make the evening special, and their warmth and professionalism deserve every bit of praise—so much so that I made sure to tip generously.
Unfortunately, our experience was overshadowed by a deeply unpleasant interaction with the man working the dock. Despite not having any guidance on what time to arrive, we were at the dock and boarded with time to spare. Unfortunately, we were repeatedly rushed in an aggressive and unnecessary way—receiving calls, texts, and even being yelled at to move faster. We were shocked. Frankly, it’s hard to understand behavior like that from someone in the hospitality business. The boat left on time, so the stress and rudeness served no purpose other than to dampen what should’ve been a joyful start to the evening.
It’s disappointing to leave fewer stars than the crew deserves, but that one individual soured the overall experience. I hope management takes note—because the team onboard is doing exceptional work, and they deserve better representation at the dock.
Review provided by Tripadvisor
Nora_l
May 12, 2025
Boat was not going that... - Boat was not going that day. We drove from
Belfast on Mothers Day. I got tickets online some time ago.We were told that boats not going until end of month.
My grandson was so disappointed.
I will not recommend you to friends who come to Maine often to visit their family
Review provided by Viator
