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Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$195-$850
Fishing Charters
Let a captain do the driving while you do the fishing
$90-$475
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$85-$500
Sailboats
Set sail with these traditional wind-powered boats
$150-$1,150
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$150-$200
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$70-$175
Kayaks
Who says you need a motor to have fun on the water?
$45-$250
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$300-$325
Canoes
A classic option for leisurely paddling
$10
JL
Jeremy
Boston Harbor Tours with Captain David
David is absolutely amazing! I had an idea to propose to my now fiancé on one of the islands in the Boston Harbor, and David was on board from the very beginning! I had never been before, so he provided tons of info and suggestions to make the whole process much easier. He was very communicative and flexible to work around my schedule to make it all happen. When the actual day came, he was punctual and gave me updates the entire day. His pricing is also excellent for what you get, so don’t let this listing fall under your radar! Overall, he was the perfect boat captain for us, and we are so happy he was a part of our big day!
Kirstin
Boston Harbor Tours with Captain David
Captain David was very quick to respond. Communicated great and was safe and a great Captain with lots of information. Definitely accommodating! I would recommend to anyone looking for a good time out on the water while in Boston or the surrounding area’s!
KK
Kimberlee
Boston Harbor Tours with Captain David
Captain David was very accommodating with pickup/drop off! He communicated well with regards to coordinating timing and even filled the cooler with ice for us before our trip! He was extremely respectful and catered our day to whatever we wanted to do. We cruised the harbor and stopped for a swim. Would absolutely recommend booking a trip with him!!
KH
Kai
Boston Harbor Tours with Captain David
We were a party of 5 and fit very comfortably. Captain David is professional, knowledgeable and have great communication. We had such a fun day cruising in the harbor then floated by one of the island. Had lunch, jumped in the water. Such a fun day! Highly recommend!
DD
Dea
Boston Harbor Tours with Captain David
Our booking relied solely on the website and comments. Thankfully there were NO surprises. Capt David easily answered all of our questions about boating/nautical and the Boston Harbor. He was accomdating to our time and temperament. We will ride with Captain David again.
Kate
Boston Harbor Tours with Captain David
Wonderful charter! Went out on a sunset cruise with a total of 6 of us. We all fit very comfortably and the boat was extremely clean. Captain Dave knew so much about the water-side Boston areas and was a tour guide in addition to a knowledgeable boat captain. He is very laid back and welcoming. Extremely communicative and gives great advice on making the most of a ride - we saw so many sights and places you can’t see from the city. Absolutely recommend Captain Dave and his boat. Can’t wait to book our next cruise!
Find the right listing for you and your crew, with options for boat types, group size, captained or self-charter, and lots more.
Found one you like? Send a rental inquiry with your preferred trip details, and you’ll receive an offer from your captain to book.
Coordinate a pick-up place and time, meet your boat captain, and get out onto the water!
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