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Classic Sail Boston

Boston, MA 02128
+1 844-724-5267
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Review Highlights
Highlight of our Boston Family Vacation!

My family of 4 booked a 4 hour sailing trip with Capt. David on the Capitiva during our stay in... read more

Reviewed 3 days ago
K_Ewing413
,
Zachary, Louisiana
Family Sailing Adventure

Our family of 5 booked a 2 hour charter with David and Classic Sailing on July 5th. It was a... read more

Reviewed 1 week ago
Krefts
,
Elbow Lake, Minnesota
via mobile
Read all 27 reviews
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We offer private sail charters and tours of Boston Harbor and Boston Outer Harbor Islands aboard a classic wooden Chesapeake Sloop 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.
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Closed Now
Hours
Hours Today: 9:00 AM - 9:00 PM
Suggested Duration: 2-3 hours
LOCATION
Boston, MA 02128
East Boston / Logan Airport
CONTACT
Website
+1 844-724-5267
Write a ReviewReviews (27)
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"captain dave"
in 4 reviews
"highly recommend this experience"
in 2 reviews
"an unforgettable experience"
in 2 reviews
"skiing"
in 10 reviews
"boat"
in 13 reviews
"photos"
in 3 reviews
"ships"
in 2 reviews
"waterfront"
in 2 reviews
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1 - 10 of 27 reviews

Reviewed 3 days ago

My family of 4 booked a 4 hour sailing trip with Capt. David on the Capitiva during our stay in Boston. We thoroughly enjoyed our time on the boat with Capt. David and his lovely wife Catie. They had water and cold drinks on the...More

Thank K_Ewing413
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Reviewed 1 week ago via mobile

Our family of 5 booked a 2 hour charter with David and Classic Sailing on July 5th. It was a fantastic family memory we will always cherish. His replica ship, the Captiva, is unique and charming. David was so easy to work and visit with...More

Thank Krefts
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Reviewed June 11, 2018

My three girlfriends and I took Captiva the sailboat out with David last week for a birthday celebration. David and his wife were such a pleasure from the initial inquiry until we stepped off of the boat. Funny enough, it was also David the captains...More

Thank Lyndsay S
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
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Reviewed September 29, 2017

We called David the day before, and he was able to squeeze us in for the next day already. It was a very spontaneous decision for us to do this, but it was really amazing. We had our younger children on board, and our son...More

Thank Camilla C
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Reviewed September 25, 2017

My husband and I booked this as part of our anniversary celebration. We had to cancel last minute and Captain Dave was very flexible with us. He is very knowledgeable, friendly and easy going. We had a great time and the views were amazing. We...More

Thank Ivette H
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Reviewed August 29, 2017

For the second straight summer, our family group had a great sail with Captain Dave. The new boat is a little larger and more comfortable for our group,of six adults. We had a great time on the harbor on a great weather day! Highly recommend!

1  Thank Tribe77
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Reviewed August 29, 2017

We took a sunset cruise around Boston Harbor in mid-August. Words cannot describe what an amazing experience this was. The sailing was smooth and the views were fantastic. Our captain was both attentive/informative and also allowed plenty of independent time for our group. We were...More

Thank brigitte_vee
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Reviewed August 11, 2017 via mobile

One of the best birthdays I have had in a long time! We did a have day tour with David and it was such a blast! Beautiful views of downtown Boston and surrounding islands. I have lived in Boston for over two years and this...More

Thank Hallie M
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Reviewed August 5, 2017

I cannot recommend this sail enough. My entire family agreed that it was the absolute highlight of our trip to Boston. David was fantastic and the time we had on the water was amazing. We had a great time in Boston, but it was so...More

Thank RPodvia
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
David P, Owner at Classic Sail Boston, responded to this reviewResponded August 6, 2017

Thank you, Rob. You and your family were a pleasure and we look forward to your next time aboard!

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Reviewed June 21, 2017 via mobile

The event was very well organised and although there were lines to see the ships, it was well managed. We did not carry handbags and that significantly cut down wait times. I personally liked the Union and Esmeralda although the Humboldt was a class apart...More

Thank Wunderluft
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
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