Classic Sail Boston — Local services in Boston

Captain Dave is the kind of guy that not only oozes knowledge of sailing, the route, and surroundings on your trip, but he also fit into to group seamlessly and doesn't feel like an outsider... and that makes it feel like you're on the water with a bunch of friends and one just happens to own a boat.

First, we had to reschedule our trip from last year as I was hospitalized and unable to make the original trip. My wife contacted Dave and they refunded us initially without hesitation. These are not only professionals, but people with kind, large hearts. The policy could have easily taken our money but we were able to reschedule and not have to pay any additional fees or money given our extenuating circumstances.

The boat is clean, well-kept, and the comms and instructions were passed along early and with plenty of detail to leave no room for misinterpretation. Payment and scheduling were easy (as my wife told me, at least) and expectations were set as to what was (and was not) provided in the cost.

As far as the value and trip itself, it's money well spent. We've done dozens of chartered routes along the coasts as well as in the Caribbean when we travel. Captain Dave was easily in the top 3 in terms of overall experiences and how effortless the day felt. It wasn't too long or too short, and Dave made sure to capture plenty of moments and memories for us instead of all our photos missing one (or more) members of the group. We also got to stop at 2 of the islands and swim around for a bit at each of them before returning back to the docks.

There were 6 people in our group and we had plenty of space for all of us, 3 backpack/YETI soft coolers, and about 4 bags of food/snacks. There is also a shaded area if you forget sunscreen and/or just need to get out of the wind or sun.

If you're curious or wondering if you may enjoy an experience like this, my best advice to you is just book it and don't overthink it. It surpassed all my expectations and was a blast of a way to spent a hot, sunny Saturday in the summer. Given the other reviewers' experiences, it doesn't seem like anyone has had a bad experience with any of the captains either. If you have anywhere near the experience I did, you'd be okay with paying double what we did for the day... it's just that much fun.

Thank you to everyone at Classic Sail for the kindness, understanding, and above all - the awesome product/experience. You've made a few new fans in the...

Absolutely stunning sunset sailboat tour on Boston Harbor! The boat was beautiful and meticulously maintained, providing the perfect setting for a memorable evening. Captain Dave was fantastic and very knowledgeable of the surrounding area. His kindness made us feel very welcome and we were instantly immersed in the environment. The weather was perfect and Boston Harbor provide breathtaking views. One of the highlights was getting the chance to steer the sailboat ourselves, adding a unique experience and provided great opportunities for photos. Passing by the USS Constitution was also memorable and Captain Dave's restaurant recommendations on the North Side were spot on. He even dropped us off nearby, adding a personal touch to an already incredible experience. Highly...

This was probably one of the best days I can remember. If you are just contemplating doing this, do this! You will not regret it! And use this company, family owned and operated with someone who is the epitome of achieving their dream! The boat is wonderful and his own labor of love. We had an exceptional day of weather on our four hour journey out to the Boston islands. As a family now of six with the addition of my two daughters-in-laws, we have traveled the world together and everyone agreed this will be a memorable day we will all cherish. I wish Captain Dave much success and am grateful for his expertise and passion! Don’t go with some corporate entity, go with someone who truly loves...