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Review Highlights
Foggy Day Fun

As “summah people” in Boothbay Harbor, we hosted friends from Michigan for their first trip to... read more

Reviewed 3 days ago
Thomas H
via mobile
Sail on the Schooner Eastwind

We really enjoyed our sailing tour of Boothbay Harbor on the Schooner Eastwind. Captain Tom and his... read more

Reviewed 6 days ago
Needham, Massachusetts
Read all 334 reviews
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  • Excellent93%
  • Very good4%
  • Average1%
  • Poor1%
  • Terrible1%
Travellers talk about
“captain john”(9 reviews)
“hour sail”(20 reviews)
Sail the waters of delightful Boothbay Harbor on our 65-foot schooner. See lighthouses, the outer islands, and sea wildlife on a two hour cruise. The Smith family has 30 years of boat building and sea adventures to share with you.
20 Commercial St, Boothbay Harbor, ME 04538-1821
+1 207-633-6598
Reviews (334)
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All reviewscaptain johnhour sailsailing experiencesunset cruisegreat sailingbeautiful sailboatgreat storiestwo hoursticket boothfantastic tripperfect weatherwonderful afternoongreat jobpoints of interestsaw sealsmaine coasthighly recommend this trip
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1 - 10 of 330 reviews
Reviewed 3 days ago via mobile

As “summah people” in Boothbay Harbor, we hosted friends from Michigan for their first trip to MAine. Wanting to provide all the quintessential experiences we booked a sail on the Eastwind schooner. Even on a fogbound day we enjoyed a leisurely afternoon meandering around the...More

Thank Thomas H
Reviewed 6 days ago

We really enjoyed our sailing tour of Boothbay Harbor on the Schooner Eastwind. Captain Tom and his 1st mate were very friendly and made our sail even more enjoyable. Captain Tom's knowledge and experience was enhance by his obvious passion and joy of sailing. Several...More

Thank nickarnao
Reviewed 1 week ago

Captain and crew were fantastic, knowledgeable and cheerful. We had super wind, the sun was shining, and everyone had a great time!

Thank travel207andbeyond
Reviewed 1 week ago via mobile

Loved the tour of harbor. Captain and mate were friendly and knowledgeable. My daughter and I got to steer the boat and help raise the sails. It wasn’t busy (10 passengers) and we saw minke whales and dolphins. I missed the seal! Teenage daughters enjoyed...More

Thank colinwynd
Reviewed 1 week ago via mobile

We went on a sunset sail last weekend with friends. Besides another couple we had the boat to ourselves. Enjoyed our trip immensely. The only suggestion I would make is they should change the time of the sunset sail to 6:30-8:30 to more accurately time...More

Thank drwuf
Reviewed 2 weeks ago

The 2018 July 4 Boothbay Harbor cruise was a disappointment. The captain did not seem to know the harbor well and the first mate was more concerned about his viewing the fireworks than paying passengers. The ship was not as close to the firework display...More

Reviewed 2 weeks ago

Michael and Tom were an excellent crew and Michael was extremely knowledgeable about the area. We were fortunate because we were the only two that signed up for the 10:00 tour. Nice smooth ride, no need to worry about sea sickness. It was fun to...More

Thank Kwanyen
Reviewed 2 weeks ago via mobile

Extremely satisfied with our experience on Schooner Eastwind. It was our anniversary and I can’t think of a better way to celebrate and soak in the scenery of Boothbay. Outstanding crew with a laidback and unpretentious, yet engaging attitude. I’ve been on the larger charters...More

Thank shauns202
Reviewed 2 weeks ago via mobile

Took the 3:00 sail yesterday (a Saturday). There were I think 20 of us on the boat, passengers ranging in ages from 5 to older middle aged. There was a French-speaking group. I think the trip was full, but each of us had plenty of...More

Thank anmd
Reviewed 2 weeks ago via mobile

The skies were threatening but Captain John was confident that it would be a night to be remembered. First Mate Patrick was a proficient sailor and knew everything about every question we asked! The front moved our and the rainbows came in! All 5 sails...More

Thank JerseyAmy
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Questions & Answers
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Janet G
8 September 2017|
AnswerShow all 3 answers
Response from eastwindbb | Property representative |
Hello and thank you for visiting us. We are open this year through Monday, October 9. This time of year our sailing schedule changes so it's best to check in with the ticketing booth for each day's trips. We hope to see... More
2 May 2017|
Response from eastwindbb | Property representative |
Thank you for contacting us regarding sailing on Schooner Eastwind. Yes, reservations are necessary especially during the time you are here. Windjammer Week begins on June 26 with many activities going on in the town... More
Jeanine M
19 April 2017|
AnswerShow all 2 answers
Response from eastwindbb | Property representative |
We will be happy to see you back on Eastwind! And yes, your granddaughter will safely enjoy the sail The trip you were on last year was certainly an unusual situation with the kayakers needing our assistance. The captain... More