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    Boston Yacht Charters

    3.4 (8 reviews)
    Closed 8:00 am - 10:00 pm

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    Classic Sail

    Classic Sail

    4.9
    (55 reviews)

    Captain Dave is the kind of guy that not only oozes knowledge of sailing, the route, and…read moresurroundings 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 Boston area!!!

    What a great experience! We sailed with Captain David on a beautiful day in early May. Because my…read morepartner has such a strong desire to learn to sail, he asked a lot of questions to learn about the vessel and different verbiage. David enthusiastically answered every question, while also giving us lessons on different sights around the sail. Highly recommend - hope we can make it back another day!

    Sunset Yacht Rentals

    Sunset Yacht Rentals

    5.0
    (3 reviews)

    We have an annual girls cruise and for the past two years went with the boat Trilogy. This year we…read morehad a larger crowd so we went with Champagne Lady. Both boats do not disappoint. Lily who was my point person was beyond accommodating. Whenever I called about any of my questions be it; WiFi, increasing my group or changing from two hours to three she was delightful. It's a cash bar with a huge wireless speaker, plenty of seats, two levels, in side and outside seating, two bathrooms and you can bring your own food. We will be back it was a night full of memories.

    You can rent the Trilogy, a Broward 103' cruising yacht privately by the hour for weddings,…read moreparties, business outings, overnight, multinight excursions, etc. sunsetyachtrentals.com. The rental price is hourly with a 2 hour minimum and includes the captain and one crew member. She is cleaned and sanitized after each charter trip and staff wear masks and maintain safety precautions throughout the trip. Plenty of room for setting up food, we had half catered and half our own. Restaurants at the dock happy to accommodate. Lots of space on this yacht to sit, wander and enjoy the ocean views. Bring your own download music from spotify or apple they have a music system. Captain Kevin and crew were very accomodating. Captain is highly experienced with Boston Harbor and crew helped set up the food and was all around a help and pleasant. Very understanding to the different needs of clients from parties to business meets. The sail was smooth and wouldn't know you were on a yacht no rolling or rocking, just beautiful views everywhere. We couldn't ask for a better trip. I booked through an on line site which eventually was routed to Sunset Yacht Rentals, they have a website. The rental was easy with documents signed through edoc ,deposit with credit cards, easy smooth transaction. The yacht has a mini hot tub, 4 bedrooms, indoor and outdoor seating venues on the yacht, full bathrooms. A cart at the dock made it easy to load the food and beverages. There is parking on Victory Rd. up to 2 hours, we were out for 3 and had several vehicles. None of us had a problem. Also a parking garage about a 10 minute walk. I rented the Trilogy for sea burial of ashes for my father. Will come back next year and rent for a party with family and friends once co-vid is more manageable.

    Boston Yacht Charters - boatcharters - Updated August 2026

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