Duchess of Boston Sailing Charters

I took my girlfriend on a private 2 hour sunset harbor cruise with Capt. Chris for our 1 year anniversary and couldn’t be happier! I wasn’t sure at first if I should take her on one of the larger boats like the odyssey or to go with the Duchesses. In the end I knew I had made the right decision when I saw how happy and amazing my girlfriend was with the views and experience. Capt Chris was extremely friendly and accommodating the entire trip. He was knowledgable about the area and made sure we got the best possible view of the Boston sunset. He even picked up fresh lobster rolls for us and provided wine glasses to make the night even more special. I would 100% recommend choosing Capt Chris and «The Duchess» over one of the larger, less intimate trips/​boats. You know you are on the right boat when guests on the other boats are taking pictures of you haha and you will never get views of the city like this!
Thanks Capt Chris!

When you have a free evening and want to cruise in a very personal and private trip around the harbor, this is the best way to do it. Captain Chris is a safe and experienced sailor, as well as a wonderful guide and host. I’ve been on 2 charters with Chris. First with my family and we had a wonderful time. Knowing how much fun my girlfriend (at the time) had on the boat, I thought it was the perfect place to get engaged. So I planned a surprise trip around the harbor for her — that Chris helped make seem like a casual, spontaneous excursion. I told her we had a party to attend, and that it was at the boat house at the end of the wharf. When we arrived we saw the Duchess and waved to Chris who invited us to go for a ride. About 10 minutes in, I pulled out the ring (upside down), my girlfriend (now wife) had no idea thanks to Chris’s ability to pull off a great surprise. Chris kept the boat steady and slow, so I didn’t drop the ring into the Harbor.
Additionally, we found out that Chris could marry us as he is a licensed minister in the Commonwealth of Massachusetts. So 15 months later, this past September, Chris performed our marriage ceremony on Cape Cod. Really can’t say how grateful I am of him and his team (his wife Cheryl).
Thanks for all you have done for us Chris. Looking forward to many more pleasant evenings on the Duchess.

We had a great time out on the harbor with Captain Chris. He was very responsive during the booking process, helpful in providing all the required information, and delightful in person on the boat. We learned a little bit about sailing and enjoyed a spectacular sunset.
This was the perfect way to see the city and the sunset, even for a local.

We had a great time with Captain Chris. We decided to do a sailing trip as part of a team outing. It was an authentic sailing experience, if you wanted to help you could, or you can just sit back and enjoy the ride. We had a great time and Captain Chris is really charming and warm and knows his stuff. Would definitely do it again!

Captain Chris was great, he help me set everything up quickly for a perfect proposal night with my now Fiancée. He met me earlier that day so I could drop off some champagne and treats that would be aboard when we arrived, it was a surprise to her that we were going for a sail. The sail was wonderful and Captain Chris has a very warm and welcoming conversation and makes the whole trip enjoyable and the gave us some extra space during the actual proposal. He took some nice pictures for us and seemed genuinely excited for us as did his wife when we got back to the harbor, she is also very very sweet and nice. Captain Chris took us on a beautiful sunset cruise over to the USS Constitution and we were in perfect position to see the cannon fire at sunset. Just a great experience and I highly recommend his charters to others. Also he takes Visa and MasterCard which is very convenient.

Pretty awesome. Granted, I did go sailing on a beautiful day so that made the experience phenomenal, but it would have been enjoyable on an ok day too.
Captain Chris does all the work sailing a small friendship sloop and lets you join in as much or as little as you’d like. The boat is beautiful and provides enough room for 6 guests to sit comfortably. The sail itself was wonderful and seemingly unplanned — it was nice to just go where the boat takes you.
Reasonably priced for what is offered — definitely worth it.

Just got back from the 4 hour sail that turned into a 6 hours sail around Boston Harbor for no extra charge. Captain Chris showed us around the inner and outer harbor, made a stop at Spectacle Island and gave us a little lesson in sailing. Could not have asked for more or a better time. It is limited, maximum of 6 people, but it is truly an enjoyable way to spend a day. Captain Chris does have some amenities, but we brought everything we needed for the lunch and afternoon sail. Highly recommend this if you’re looking for a relaxing time and you will not be disappointed.