Schooner Eastwind 2 Hour Day Sail in Boothbay Harbor
Recommended by 90% of travelers
Maine, USA
- 2 hours (approx.)
Why travelers loved this
·
Overview
What's Included
- Restroom on board
- BYOB snacks and drinks (non-alcoholic)
- Gratuities
- Alcoholic BeveragesSelection of beer, wine and liquor drinks available for purchase
Meeting and Pickup
Meeting point
- 20 Commercial St, Boothbay Harbor, ME 04538, USA
In Boothbay Harbor, look for the sign that says "Schooner Eastwind."
End point
This activity ends back at the meeting point.Ticket Redemption Point
20 Commercial St, Boothbay Harbor, ME 04538, USA
Itinerary
1
Boothbay Harbor Region
2 hours • Admission Ticket Free
Additional Info
- Confirmation will be received at time of booking
- Not wheelchair accessible
- Near public transportation
- Infants must sit on laps
- Most travelers can participate
- This tour/activity will have a maximum of 28 travelers
Supplied by
Cancellation Policy
You can cancel up to 24 hours in advance of the experience for a full refund.
Traveler Photos
Featured review
Kimberly_C
Easy to access and we boarded our Schooner, the Eastwind … helmed by Capt Josh & first mate, Maricin - where we sailed amongst a fierce and competitive regatta competition! Out to the edge of the Atlantic Ocean … it was a gorgeous day and we enjoyed some great winds and heeled beautifully … and, of course … more lighthouses … the best seen was Burnt Island Light … we were just a wee bit too far to zoom in on Ram Island Lighthouse — we tried! It was a spectacular afternoon of sailing. Highly recommend.
Reviews
4.6
based on 141 reviews
Sort by: Most insightful
Katherine_B, Jul 2026
The ride was beautiful with lovely coastline to take in and frolicking dolphins and seals along the way. The crew was entertaining and made the trip a blast.
Response from Host, Jul 2026
Thank you so much for your wonderful review! ⛵😊 We’re thrilled to hear you enjoyed the beautiful coastline and had the extra treat of seeing dolphins and seals along the way. Those wildlife moments make a sail truly special!
We’re also delighted that our crew helped make your trip fun and entertaining. They love sharing the experience with our guests and creating lasting memories on the water. Thank you for sailing with us, and we hope to welcome you aboard again soon for another unforgettable adventure! 🌊🐬☀️
Suzanne_S, Jul 2026
Time on the water in the schooner was lovely. The captain and crew were friendly and helpful. The views were great. I had hoped to go a little farther out of the bay, but it was still great and would highly recommend.
Response from Host, Jul 2026
Thank you so much for your kind review! ⛵😊 We're delighted to hear you enjoyed your time on the water and that our captain and crew helped make the experience so enjoyable. We appreciate your feedback about venturing farther out into the bay, and we're glad the beautiful views still made for a memorable sail. Thank you for your recommendation—we hope to welcome you aboard again soon!
Nicole_F, Jul 2026
We had a great time on the schooner - we were also lucky that the weather was perfect, sunny and just the right amount of wind to make it amazing! The crew was great too, friendly and knowledgeable.
Response from Host, Jul 2026
Thank you so much for the wonderful review! ⛵😊 We're delighted to hear you had such a beautiful day on the water with perfect sailing conditions. It's great to know our friendly and knowledgeable crew helped make your experience even more memorable. Thank you for sailing with us, and we hope to welcome you back aboard for another amazing adventure soon!
Gegory_W, Jul 2026
This was a great experience the captain was wonderful his first mate was absolutely wonderful. They were very informative and made our trip especially nice.
Response from Host, Jul 2026
Thank you so much for the wonderful review! ⛵😊 We're delighted to hear you had such a great experience. It's wonderful to know the captain and first mate made your trip so enjoyable with their knowledge and hospitality. We truly appreciate your kind words and hope to welcome you aboard again for another memorable sail soon!
Patricia_M, Jul 2026
The crew was friendly and accommodating. Captain Matt is a confident and knowledgeable sailor, and shared interesting facts about the Maine coast and history. Ryan was very attentive and helpful.
Response from Host, Jul 2026
Thank you so much for the wonderful review! ⛵😊 We're delighted to hear you enjoyed your sail with Captain Matt and Ryan. We'll be sure to share your kind words with them. It's great to know Captain Matt's knowledge of the Maine coast and history, along with Ryan's attentive service, helped make your experience so enjoyable. We hope to welcome you aboard again soon!
Jeannette_K, Jun 2026
Matt and Brian were great, Matt was full of information, made the experience very enjoyable ! Answered many questions and allowed the guests to help with the sails.
Response from Host, Jun 2026
Thank you so much for the kind review! ⛵😊
We’re thrilled to hear Matt and Brian helped make your sail such an enjoyable experience. Matt will especially love knowing his knowledge and storytelling added to your time on the water, and that you enjoyed getting hands-on with the sails—that’s always a guest favorite.
We truly appreciate you sailing with us and hope to welcome you back aboard for another fun and memorable trip soon! 🌊🌅
Sharon_c, Jun 2026
This was our favorite part of Boothbay‼️ Captain was very knowledgeable and friendly, his helper was quick to answer questions and to help. I absolutely loved the views plus it was so relaxing sailing around the bay. I’d definitely go back again
Response from Host, Jun 2026
Thank you so much for the fantastic review! ⛵😊
We’re honored to hear that sailing with us was your favorite part of Boothbay! It’s wonderful to know you enjoyed the beautiful views, relaxing time on the water, and the friendly, knowledgeable service from both the captain and crew.
Your kind words mean a lot to us, and we’re thrilled you had such a memorable experience. We’d love to welcome you back aboard the next time you’re in Boothbay for another relaxing sail around the bay! 🌊🌅
Tatiana_R, Jun 2026
We enjoyed exploring Boothbay Harbor on this schooner. The captain allows passengers to assist with raising and lowering the sails. We enjoyed learning about the history of this area.
Response from Host, Jun 2026
Thank you for the wonderful review! ⛵😊
We’re so glad you enjoyed exploring Boothbay Harbor from the water and learning about the area's rich history along the way. One of the best parts of sailing on a traditional schooner is the opportunity to get involved, and we’re happy you enjoyed helping raise and lower the sails.
Thank you for joining us, and we hope to welcome you back aboard for another memorable sail in the future! 🌊🌅
Ulla_C, Jun 2026
Wear good shoes and jacket/ rain gear.
You will have a chance to set sail !
Beautiful sailing and views of Maine’s coastline and islands .
Captain Matt and ship mate Haley very informative and knowledgeable.
Comfortable seating and you are free to move around the ship.
Response from Host, Jun 2026
Thank you for the wonderful review! ⛵🌊
We’re so glad you enjoyed the beautiful views of Maine’s coastline and islands and had the chance to help set sail. Those hands-on moments are what make these trips so memorable!
Captain Matt and Haley will be thrilled to hear your kind words about their knowledge and hospitality. We also appreciate the helpful advice for future guests—good shoes and weather-ready layers can make all the difference on the water.
Thank you for sailing with us, and we hope to welcome you back aboard for another adventure soon! 😊
Marlee_V, Jun 2026
Captain Dawson was super knowledgeable and very entertaining. We love the opportunity to raise the sale and steer the skooner. We loved it so much we tried to do it the next day as well.But the weather wouldn't cooperate
Response from Host, Jun 2026
Thank you so much for sharing your experience! ⛵😊
We’re thrilled to hear Captain Dawson was both knowledgeable and entertaining, and that you enjoyed the hands-on experience of raising the sails and steering the schooner—that’s always a guest favorite.
Sorry the weather didn’t cooperate the next day, but we love that you were eager enough to try again! That means a lot. We’d be happy to welcome you back aboard anytime for another chance at smooth sailing and great conditions. 🌅
Rick_Y, Oct 2025
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.
Response from Host, Oct 2025
Thank you for sailing with us again and for being such a loyal guest over the past 14 years — we truly appreciate your continued support. We’re sorry to hear this trip didn’t meet the high standards you’ve come to expect from Eastwind. While our captains always do their best to maximize time under sail, there are times when wind direction or traffic in the harbor requires occasional use of power or course adjustments for safety and timing.
We also appreciate your comments about narration and overall engagement — that’s helpful feedback, and we’ll be sure to review it with the crew so that returning guests continue to enjoy the same memorable experience that first brought them aboard.
We hope you’ll give us another chance to provide the relaxing, full-sail experience you’ve come to know and love.
chitteroc, Oct 2025
Beautiful ship, with a small number of passengers and a really fun crew. Our Captain Sarah and Mate Christine were excellent!
Response from Host, Oct 2025
Thank you so much for sailing with us and for your kind words! We’re so glad you enjoyed the smaller, more personal experience on board and had fun with Captain Sarah and Mate Cristina. They’ll be thrilled to hear your praise. We hope to welcome you back on deck for another adventure soon!
Don_B, Oct 2025
It was a windy fall day so make sure you bring a jacket under those circumstances otherwise dress accordingly
Response from Host, Oct 2025
Thank you for your wonderful review! We’re so glad you had a fun, interactive experience and enjoyed helping hoist the sails. It’s great to hear the views and the crew made your sail memorable. We’d love to welcome you aboard again for another amazing trip!
Myra_S, Oct 2025
Amazing. Fun. Beautiful views. Great captain and mate. Such a good time with interactive hoisting the sails.
Response from Host, Oct 2025
Thank you for your fantastic review! We’re thrilled to hear you had such a fun and interactive experience, and that the captain and mate helped make it memorable. It’s wonderful that you enjoyed the views and even got to help with hoisting the sails. We’d love to have you aboard again for another amazing sail!
Sherri_D, Oct 2025
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!
Response from Host, Oct 2025
Thank you for such a wonderful review! We’re thrilled to hear that the captain and crew made your experience fun, comfortable, and memorable. It’s great to know the little touches, like blankets, added to your sail. We’re so glad you enjoyed the schooner and felt the trip was a great value. Your strong recommendation means the world to us — we’d love to welcome you aboard again!
Steve_D, Sep 2025
Outstanding sailing experience, we thoroughly enjoyed it! Captain and 1st mate were very enjoyable and engaging with everyone.
Response from Host, Oct 2025
Thank you so much for your wonderful review! We’re thrilled to hear you had such an outstanding experience and enjoyed spending time with the captain and first mate. They truly enjoy connecting with guests and making each sail special. We look forward to welcoming you back aboard for another great adventure!
Heather_P, Sep 2025
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..
Response from Host, Sep 2025
Thank you for sailing with us and sharing your thoughts. Even on the cool, cloudy days when the wildlife decides to stay hidden, the sail itself still has a way of offering its own quiet charm. We’ll take your note on narration to heart—sometimes the sea does the talking, but we’re always glad to add a voice to the story. We hope you’ll join us again for a sunnier spin when the harbor is bustling with wildlife.
Debbie_L, Sep 2025
Riding the waves on a sailboat is a beautiful experience. If you decide to go in late September make sure you wear warm clothes with layers and a hat. You hey did provide blankets which I took full advantage of and. It was fabulous.
Response from Host, Sep 2025
Thank you for sharing your experience! We’re so glad you enjoyed the beauty of sailing and stayed cozy with the blankets on board. Great advice, too—layers and a hat definitely make late September sails more comfortable. We’re thrilled to hear it was a fabulous trip for you and hope to welcome you back again!
Nancy_C, Sep 2025
This was a beautiful way to discover some of the coastal areas of Maine. It was absolutely stunning .
The captain and mate were very informative and showed everyone a good time
Response from Host, Sep 2025
Thank you so much for sailing with us! We’re delighted to hear you enjoyed discovering the beauty of Maine’s coast—it truly is stunning. We’re glad the captain and mate helped make your trip both informative and fun. We’d love to welcome you back for another sail someday!
Jill_T, Sep 2025
Relaxed informative very enjoyable . Sarah and Mareson were the best. They actively let passengers participate in hoisting the sales.
Response from Host, Sep 2025
Thank you for sharing your experience! We’re so glad to hear you had a relaxed, enjoyable sail and that Sarah and Mareson helped make it special. They love getting guests involved, and it’s wonderful to know you enjoyed participating in the sailing. We hope to see you aboard again soon!
Jason_Z, Sep 2025
The captain and the deckhand were fun and very knowledgeable. And they let us participate in the raising of the sails.
Response from Host, Sep 2025
So glad you had fun with the crew and got hands-on with the sails—it’s always more memorable when you’re part of the adventure. Thanks for sharing your experience, and we’d love to have you back aboard for another sail soon.
Peter_G, Sep 2025
We had a wonderful time on the water. Weather was perfect bright sun and enough winds for smooth sailing
Response from Host, Sep 2025
We’re so glad the weather gave you just the right mix of sunshine and breeze—it makes for the best kind of sailing day! Thank you for joining us, and we hope to see you back on the water again soon.
Steve_L, Sep 2025
Beautiful day and lovely sailing experience! Luke and Michael were wonderful and made the trip a good one. Highly recommend.
Response from Host, Sep 2025
We’re so glad you had a beautiful day on the water! Captain Luke and Michael will be delighted to know they helped make your sail such a great experience. Thank you for the recommendation—we’d love to have you aboard again!
Darlene_L, Sep 2025
The crew was awesome and it was a nice ride, but unfortunately it was too foggy and could not see much. Only view was the fog. Wish they would have canceled or given back some portion of a refund or credit towards another ride.
Response from Host, Sep 2025
Thank you for your review and for recognizing our crew. Unfortunately, weather conditions such as fog are outside of our control and do not impact the safety of the trip, which is why we still operate. While the views may not have been ideal that day, many guests still enjoy the sailing experience itself and the crew’s hospitality. For that reason, refunds or credits are only provided when we must cancel due to unsafe conditions. We hope you’ll join us again on a clear day to fully enjoy the scenery our trips are known for
Vicky_K, Sep 2025
Rescheduled to different boat, via phone call.
Drove an hour from Bath to Booth Bay Harbor.
Cruise was canceled due to stormy weather.
Hope we get refund- with out complications.
Response from Host, Sep 2025
We’re sorry the weather did not cooperate on the day of your scheduled sail. For safety reasons, trips must occasionally be canceled during storms, and in your case we processed a full refund immediately. While we understand the disappointment, a 1-star review does not reflect the actual experience on our boat, as the trip never took place. We hope you’ll give us another chance in the future when conditions are favorable.
Margaret_H, Sep 2025
Great day for a sail out of Boothbay. The captain and crew were great! The EvenTide is a beautiful boat and the ride was smooth!
Response from Host, Sep 2025
Sounds like the perfect day on the water! The crew will be happy to know they made your sail as smooth and enjoyable as the boat herself. Thanks for sharing your kind words—we’re so glad you joined us!
Karen_W, Sep 2025
Enjoyable and quite relaxing. Luke and Matterton (sp?) were an excellent crew and hosts. Would definitely recommend it to others.
Response from Host, Sep 2025
So glad you had a relaxing sail with Luke and Mareson! They’ll be happy to know their hosting skills are as smooth as the sailing. Thanks for recommending us—we’d love to welcome you back aboard anytime!
Amy_W, Aug 2025
The captain of the Eastwind and his first mate, Mareson, made our four-year-old granddaughter's first sailing experience amazing! The weather was perfect, the wind steady, and porpoises danced in our wake. The crew provided an appropriately sized Coast Guard approved life jacket, and patiently answered many questions and welcomed her 'help' with sailing the vessel.
Response from Host, Aug 2025
We’re so glad your granddaughter’s very first sailing adventure was a memorable one. The Eastwind crew loves having little sailors on board—especially those eager to “help” with the ropes and questions. Add in steady winds, perfect weather, and porpoises for company, and it sounds like the sea put on quite a show just for her! 🌊⛵🐬
Evan_H, Aug 2025
This experience was a dream come true and it was done in the highest fashion. Our captain and mate were highly skilled, attentive to guests, and extremely kind. I need’nt mention the beauty of the views. Everything about this trip was perfect and I am so happy to have taken the time. In my opinion, I could’ve sailed out there for another couple hours.
Response from Host, Aug 2025
What a beautiful reflection—thank you for sharing! We’re so glad your sail felt like a dream come true and that the captain and mate helped make it such a special experience. The views never disappoint, but it’s wonderful to hear that the kindness and skill of the crew made it truly perfect. Next time, we’ll hope to keep you out on the water for those extra hours you were wishing for! ⛵✨
Mary_H, Aug 2025
Sarah and Christine were amazing
The weather was perfect
Drinks delicious
Absolutely soooo much fun!
Response from Host, Aug 2025
Now that’s a recipe for a perfect day on the water — amazing crew, gorgeous weather, tasty drinks, and a whole lot of fun! 😄🍹⛵️
Sarah and Cristina will be over the moon to hear they helped make your trip such a memorable one. Thanks for sailing (and smiling!) with us — come back anytime you’re ready for round two!
Likely to Sell Out
From $54.95
per personup to 24 hours before the experience starts (local time)
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Schooner Eastwind 2 Hour Day Sail in Boothbay Harbor
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