Classic Sail Boston
Classic Sail Boston
5
9:00 AM - 9:00 PM
Monday
9:00 AM - 9:00 PM
Tuesday
9:00 AM - 9:00 PM
Wednesday
9:00 AM - 9:00 PM
Thursday
9:00 AM - 9:00 PM
Friday
9:00 AM - 9:00 PM
Saturday
9:00 AM - 9:00 PM
Sunday
9:00 AM - 9:00 PM
About
We offer private sail charters and tours of Boston Harbor and Boston Outer Harbor Islands aboard a classic wooden Chesapeake Skipjack sailboat. 2,4, and 8 hour private charter cruises are available. Pick-up/Drop-off locations available throughout Boston Harbor: Charlestown, East Boston, Seaport District/Downtown Boston. BYOB or let us Cater.
Boston, Massachusetts

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Travelers talk about
(9 reviews)
(16 reviews)
(21 reviews)

Most Recent: Reviews ordered by most recent publish date in descending order.

Detailed Reviews: Reviews ordered by recency and descriptiveness of user-identified themes such as wait time, length of visit, general tips, and location information.

Popular mentions

5.0
5.0 of 5 bubbles49 reviews
Excellent
49
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Kristin Z
Wellesley, MA2 contributions
5.0 of 5 bubbles
Jun 2020 • Family
I booked this trip as a special Father’s Day outing for our family and it was amazing. We’ve lived in Boston for 6 months and this has been our favorite way to see the city. Dave was an excellent guide and made it fun for all of us. From letting my husband hoist the sail, allowing our son to steer the boat, teaching us about the local history and adding us at the last minute to his already full schedule. We are extremely grateful for this wonderful experience and will always fondly remember our sunset sail on this beautiful boat. We highly recommend it!
Written June 22, 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Kristin, thank you so much for your kind words. Families like yours and evenings like that are why we do what we do. Look forward to seeing you all again!
Written June 23, 2020
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.

LePetitMer
Chattanooga, TN33 contributions
5.0 of 5 bubbles
May 2021
We had originally booked our trip for Saturday, but due to inclement weather pushed to Sunday. It was a rainy and windy Sunday, and the Captiva cut through the waves very smoothly. We were able to achieve the top speed of the vessel (13 knots?), and I felt like a pirate sailing the high seas.* Capitan Dave got us bonus ponchos so we could stay a little bit more dry. We had a wonderful time and really enjoyed hearing about the history of the Boston harbor while on a historical style vessel.

This cruise would be great for couples, families, or even bachelorette parties.

*If pirates drank canned wine, only sailed in harbors, and wore ponchos.
Written June 1, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

Lori F
2 contributions
5.0 of 5 bubbles
Jul 2020
Perfect charter with Captain Dave. I booked this as a birthday celebration for my husband. It was a stunning day on the water, great winds for sailing, and Dave could not have been a better guide and captain. Kids and adults enjoyed every minute. We will definitely book this again. It's a must-do and a great way to see Boston Harbor and some of the outer islands.
Written July 19, 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

Sonia
Boston, MA11 contributions
5.0 of 5 bubbles
Sep 2020 • Friends
Cloudy skies did not stop us from having a wonderful afternoon on the water. We were even able to stopover at Georges Island and had the entire place to ourselves! Captain David was thoughtful, knowledgeable, and hospitable.
This is the best way to see the harbor islands.
Highly recommend this private sail to locals and out of town guests looking for a unique and memorable experience.
Captiva is beautiful, and we can’t wait to book the sunset sail next!
Written September 7, 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

kimothy063
New York City, NY6 contributions
5.0 of 5 bubbles
Jul 2021
My husband & I went with 2 other couples to celebrate our 8 year anniversary. Captain David & Hunter were fantastic. They were patient with us (a couple of our friends were late) and explained/answered all of our questions. The Captiva is a beautiful sailboat. I would absolutely recommend this trip. Next time we return, we're definitely doing a full day tour.
Written August 2, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

Chrissy C
Proctor, AR12 contributions
5.0 of 5 bubbles
Jul 2022 • Couples
A beautiful way to experience Boston Harbor! We booked the 2 hour for our first trip to Boston. After booking, Katie was extremely helpful in preparing us and doing her best to accommodate us. Unforgettable and relaxing - great way to get away from the busy and have a peaceful evening! Will definitely be back and book the 4 hours to see the islands.
Written July 10, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

James Graydon
2 contributions
5.0 of 5 bubbles
Jul 2022 • Friends
Great experience; we did a sunset sail and then watched the Winthrop fireworks. The views were amazing and the boat was great; just as importantly, David and Katie were knowledgeable, friendly, and professional. I highly recommend a sail with them for any occasion.
Written July 4, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

Lisa S
3 contributions
5.0 of 5 bubbles
Jun 2020
Perfect Day.

We were celebrating Father's Day with our adult children. The weather was beautiful and we had some wind. David is a perfect host. He will give you what you want. We are interested in all things. We had four hours. He can provided you everything you want to now about sailing, the water, each of the islands, etc. He has a very comfortable presence. Would highly recommend it. The boat is absolutely beautiful and clean and has a great history.
Written June 22, 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Thank you so much Lisa! It was my pleasure having you and your family for such a pleasant sail. Enjoy the rest of your summer and hope to see you again!
Written June 23, 2020
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.

HeatherJo23
Colorado Springs, CO1 contribution
5.0 of 5 bubbles
Jun 2015 • Family
The Nanatasis is a beuatiful ship. My family and I spent an afternoon sailing, ejoying being on the water, seeing Boston and the most importantly relaxing while Captain David Puett made us feel at ease. His knowledge and charm were 2nd to none! His deck hand took care of all of our needs, getting beverages and snacks when requested. I was astounded at the low price for all of this service. This will be an event my family and I will never forget! I look forward to more adventures with Captain David!
Written June 28, 2015
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

Anup G
Birmingham, AL1 contribution
5.0 of 5 bubbles
Jul 2020
Was a great day on the water. Showed us the sights in and around Boston and was very informative. Even had one member of our group help out with getting the sail up and down which was so cool !! Highly recommend !
Written July 7, 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

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