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Open today: 10:00 a.m. - 8:00 p.m.
Review Highlights
Perfect Proposal!

I worked with Captain Chris at Duchess of Boston to plan a proposal to my Fiancee, and it was an... read more

Reviewed June 16, 2018
Grant M
Small sailboat, wonderful company, beautiful harbor

I organized a group of six to ride with Captain Chris on a sunset tour of the inner harbor. It was... read more

Reviewed August 29, 2017
Boston, Massachusetts
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  • Excellent72%
  • Very good14%
  • Average0%
  • Poor0%
  • Terrible14%
16 Jun 2018
“Perfect Proposal!”
29 Aug 2017
“Small sailboat, wonderful company, beautiful harbor”
Historic Sailing Charters of Boston Harbor aboard an Authentic Friendship Sloop. Each Charter customized for You. Private Charter. Only the Guests You choose will be on the Boat. Bring your own Food & Beverages. Relax or be part of the Crew.
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Hours Today: 10:00 a.m. - 8:00 p.m.
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87 Commercial Wharf, B Dock Slip 11, Boston, MA 02110-3800
+1 781-591-9783
Reviews (7)
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Reviewed June 16, 2018

I worked with Captain Chris at Duchess of Boston to plan a proposal to my Fiancee, and it was an amazing experience. Throughout the planning process, Chris was very responsive and knowledgeable. It really relieved a lot of the planning stress working with Chris. On...More

Thank Grant M
Reviewed August 29, 2017

I organized a group of six to ride with Captain Chris on a sunset tour of the inner harbor. It was a two hour tour on the sister boat, the Sea Hawk. (The Duchess was under repair.) Chris is fun to chat with - we...More

Thank dwvs
Reviewed August 23, 2017 via mobile

We were scheduled for a sailing trip. We scheduled in advanced and created a touring schedule around it. Two hours before our scheduled time Chris called and said "because of the eclipse " he would not take us out. We were unable to book another...More

Thank traveler122495
Christopher P, Owner at Duchess of Boston Sailing Charters, responded to this reviewResponded August 25, 2017

Thank you for taking the time to advise me of your recent experience. This was an error on my part and I acknowledge the cancellation was too close to the departure time. My standard procedure is to contact my customers the evening before the charter...More

Reviewed July 29, 2016

Captain Chris is very accommodating, personable and experienced. He knows the harbor and landmarks well so can answer your questions as you sail. The boat is comfortable and sturdy and handles waves well. We had arranged for 2 hours with an option for 3 and...More

Thank Bruce M
Reviewed June 6, 2015

Captain Chris is not your typical sailing charter that packs on bunch of people. The Duchess only holds 6 passengers. My wife and I and 4 kids had a great time. Captain Chris not only took us out for to see the harbor but taught...More

Thank Kendal M
Reviewed August 24, 2014 via mobile

My best friends and I organized a sailing trip as a part of a bachelorette party. Captain Chris was more than accommodating! He was so friendly and knowledgable. He was a great teacher but didn't make us feel like we had to work if we...More

1  Thank Chris and Carol... L
Reviewed August 16, 2014

I'm a Bostonian, and I live right in the North End by the waterfront. I've done about every tour or outing possible, and my afternoon on the Duchess is my new #1 favorite outing. I've wanted to go sailing in the Harbor for some time....More

3  Thank FlightSurgeon66
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The largest area of the city, Downtown is rich with
historical and iconic sites in Boston. Stroll through
one of Boston’s most famous green spaces, the Boston
Public Gardens, check out and make way for duckling
statues, picnic under a beautiful tree overlooking the
pond, and walk over the iconic footbridge where,
during summer time, you will catch a swan boat toting
children and eager tourists through the pond. Have
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