Schooner Eastwind 2 Hour Day Sail in Boothbay Harbor
Recommended by 91% of travelers
Maine, USA
- 2 hours (approx.)
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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
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Cancellation Policy
You can cancel up to 24 hours in advance of the experience for a full refund.
Traveler Photos
Featured review
Sherri_D
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!
Reviews
4.6
based on 167 reviews
Sort by: Most insightful
Aaron_N, Sep 2026
Great value and friendly staff. Excellent service for drinks. We will be back again! Book it don’t wait
Pamela_G, Aug 2026
We have a great time! We had 3 teenagers with us and although they were skeptical about it being “boring”, it ended up being their favorite part of vacation. It was about 80 degrees on land and chilly/windy when we got out on the water so if you get good easily definitely bring a light jacket or sweatshirt. My oldest son and husband were fine with just jeans and a tshirt. The captain and crew woman were super nice.
Response from Host, Aug 2026
Thank you so much for the wonderful review! ⛵ We love hearing that your teenagers went from skeptical to calling the sail their favorite part of the vacation! That’s a win! 😊 We’re also glad our captain and crew helped make the experience so enjoyable. And great tip about bringing a light jacket—those ocean breezes can be sneaky! We hope to see you all again!
Dorothea_S, Aug 2026
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.
Response from Host, Aug 2026
We're so glad you enjoyed you afternoon with us! We would love to see you again soon!
Julia_P, Aug 2026
Such a wonderful experience. Captain and cocaptain were spectacular. Friendly and helpful. Great trip. We will do it again.
Response from Host, Aug 2026
Thank you for the wonderful review! We are thrilled you were impressed with the crew!
Melissa_M, Aug 2026
Fun time with knowledge staff who share interesting info along the way. Perfect couple os hours spent on the water.
Response from Host, Aug 2026
Thank you so much for the great review! ⛵️ We’re thrilled to hear you had such a fun time on the water and enjoyed the interesting information shared by our knowledgeable crew. A couple of hours sailing, relaxing, and taking in the scenery sounds like the perfect way to spend an afternoon!
We truly appreciate you joining us and hope to welcome you aboard again for another wonderful sail! 🌊☀️
Michael_C, Aug 2026
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.
Response from Host, Aug 2026
Thank you so much for the wonderful review! ⛵️ We’re delighted to hear you had such a beautiful afternoon sailing aboard the Eastwind. It sounds like the friendly crew, comfortable schooner, and gorgeous weather all came together to make it a perfect day on the water.
We truly appreciate you choosing to sail with us and hope to welcome you aboard the Eastwind again for another memorable adventure! 🌊☀️
Rick_V, Aug 2026
Relaxing and scenic. The captain and first mate were upbeat and friendly . They answered all questions and thoroughly provided information about the area.
Response from Host, Aug 2026
Thank you so much for the wonderful review! ⛵️ We’re delighted to hear you found your sail relaxing and scenic. It’s great to know our captain and first mate kept things upbeat and welcoming while sharing information about the area and answering your questions.
We truly appreciate you choosing to sail with us and hope to welcome you aboard again for another peaceful and beautiful experience! 🌊☀️
Alisa_O, Aug 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.
Response from Host, Aug 2026
Thank you for taking the time to share your honest feedback.
We’re sorry that the route and overall experience didn’t meet your expectations. Our sails are designed to focus on the experience of sailing, taking in the scenery, and enjoying the water rather than traveling to a particular destination, but we understand that this may feel different from what some guests anticipate.
We truly appreciate your feedback and are glad you enjoyed seeing the lighthouse and interacting with our crew. We hope you’ll consider sailing with us again someday, and we’d love the opportunity to provide an experience that better matches what you’re looking for.
Terry_F, Aug 2026
It's a beautiful trip. The captain and his partner were very professional, polite and informative. We would definitely do this again.
Response from Host, Aug 2026
Thank you so much for the wonderful review! ⛵️ We’re thrilled to hear you enjoyed the beautiful trip and that our captain and crew helped make your experience so enjoyable with their professionalism, kindness, and knowledge.
We truly appreciate your recommendation and are so glad you’d sail with us again. We look forward to welcoming you aboard for another memorable adventure! 🌅⛵️
Rick_H, Jul 2026
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.
Response from Host, Aug 2026
Thank you so much for your wonderful review! ⛵😊 We’re thrilled to hear you enjoyed your cruise and got to experience the beauty of Boothbay Harbor from the water. Even when the skies are a little cloudy, the coastline has a special charm that makes for a memorable adventure.
We’re glad you enjoyed learning more about sailing and the history of the area. Our crew loves sharing their knowledge and helping guests connect with the unique character of Maine’s coast.
Thank you as well for sharing the helpful tip about finding Pier 4 for departure. We truly appreciate your recommendation and hope to welcome you aboard again soon for another beautiful sail! 🌊☀️
tracylfearon, Jul 2026
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!
Response from Host, Aug 2026
Thank you so much for your thoughtful and detailed review! ⛵😊 We’re thrilled to hear you had such a wonderful experience aboard the Schooner Eastwind. Matt and Brian will be delighted to know their personable, professional, and informative approach helped make your sail memorable.
We’re glad you enjoyed the smooth boarding process, onboard service, and the beautiful weather—plus the special treat of seeing seals and porpoises along the way! 🦭🌊 Those wildlife moments are always a highlight and a wonderful reminder of the magic of being out on the water.
We truly appreciate your feedback about wanting to travel a bit farther and hear more narration about the sights along the way. Guest suggestions like yours help us continue to improve the experience we provide. Sailing routes can vary based on wind, weather, and sea conditions, but we always strive to make each journey as enjoyable and engaging as possible.
Thank you for your high recommendation, and we hope to welcome you aboard again for another beautiful Maine sailing adventure! ☀️⛵
warrick_f, Jul 2026
We thoroughly enjoyed our experience on the Schooner Eastwind. There was a small craft warning the day we sailed, but Matt handled the conditions professionally and safely. Both Matt and his mate (Veronica?) were knowledgeable and happy to answer any questions we had. We saw a couple bald eagles, osprey, and seals. A fun day and I would recommend it.
Response from Host, Aug 2026
Thank you so much for your wonderful review! ⛵😊 We’re thrilled to hear you thoroughly enjoyed your experience aboard the Schooner Eastwind. Sailing in changing conditions can make for a truly memorable adventure, and we’re glad you appreciated Matt’s professionalism and careful handling of the day’s conditions.
We’ll be sure to share your kind words with the crew. They’ll be delighted to know their knowledge, friendliness, and willingness to answer questions helped make your sail so enjoyable.
Seeing bald eagles, osprey, and seals along the way was an extra special bonus from Mother Nature! 🦅🦭 Thank you for recommending us, and we hope to welcome you aboard again soon for another unforgettable day on the water. 🌊☀️
Robert_M, Jul 2026
Awesome day in the water with Matt and Brian. The weather was beautiful. Definitely recommend this trip for visitors and long-time seasonal residents alike.
Response from Host, Aug 2026
Thank you so much for your wonderful review! ☀️🌊 We’re thrilled to hear you had such an awesome day on the water with Matt and Brian. They’ll be delighted to know their hospitality helped make your experience so enjoyable.
We’re especially glad the beautiful weather made for the perfect outing, and we truly appreciate your recommendation for both first-time visitors and longtime seasonal residents. Thank you for choosing to spend your day with us, and we hope to welcome you back for another unforgettable adventure on the water soon! 😊⛵
Michelle_Q, Jul 2026
Just wonderful. The crew is outstanding. Very approachable, knowledgeable and welcoming. The boat is beautiful and the history of it is willingly shared. The water was perfect and we got to sail. The crew is open to participation from all ages. Such a relaxing and fun adventure! Highly rec. We have a teen and she loved it!
Response from Host, Aug 2026
Thank you so much for your wonderful review! ⛵😊 We’re thrilled to hear you had such a relaxing and fun adventure aboard. Our crew will be delighted to know their welcoming, knowledgeable, and approachable service helped make your experience so memorable.
We’re especially glad you enjoyed learning about the boat’s history and had the opportunity to experience true sailing. It’s wonderful to hear that your teen loved getting involved too—we love encouraging guests of all ages to participate and be part of the adventure!
Thank you for your high recommendation and for choosing to sail with us. We hope to welcome your family back aboard for another unforgettable day on the water! 🌊☀️
Susan_K, Jul 2026
Was peaceful and fun with great views of Boothbay harbor. The captain and crew were friendly and informative.
Response from Host, Jul 2026
Thank you so much for your wonderful review! ⛵😊 We’re thrilled to hear you enjoyed a peaceful and fun sail while taking in the beautiful views of Boothbay Harbor.
Our captain and crew will be delighted to know their friendly service and informative commentary helped make your experience memorable. We truly appreciate you joining us on the water and hope to welcome you aboard again soon for another relaxing and scenic adventure! 🌊☀️
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!
From $54.95
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Schooner Eastwind 2 Hour Day Sail in Boothbay Harbor
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