We use cookies to improve your browsing experience. And dolphins make us happy. Find out more about our cookies policy here.
Sailboats
Set sail with these traditional wind-powered boats
$140-$1,775
Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$205-$1,925
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$175-$450
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$150-$400
Fishing Charters
Let a captain do the driving while you do the fishing
$95-$350
Kayaks
Who says you need a motor to have fun on the water?
$425-$450
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$95-$350
JR
Jenna
34' Luxury Double Decker – Party Friendly w/Washroom 2 Hours Free!!
Ron completed our weekend in Toronto celebrating our friends bachlorette by taking us onto his boat, showing us beautiful views of the city, and being an all around personable, fun and funny captain. We enjoyed laughing and talking with him. His boat was clean and spacious. I would definitely recommend Ron and look forward to chartering with him again soon!
AP
Abraham
50’ Yacht in Oysterbay, Cruise, Paddleboard, Kayak, Tubing, optional Waverunner
My daughter and her friends had a 16th birthday party on the boat and they had an amazing time. Jeffrey was a wonderful host and the boat was incredible. Everything was exactly as described and it was a amazing experience for everyone.
PC
Priya
34' Luxury Double Decker – Party Friendly w/Washroom 2 Hours Free!!
Had a great time. Ron’s service was amazing and surprise party was successful for our friend’s bachelorette.
MM
Mathew
Just Repowered Cuddy Cabin/Walk Around bareboat fishing charter in Annapolis
William was great and we had a wonderful time on the boat. It ran flawlessly and handled the windy conditions we had that day really well. William was also very communicative and helpful with ensuring we had everything we needed. I would book with him again.
TS
Tom
Just Repowered Cuddy Cabin/Walk Around bareboat fishing charter in Annapolis
This is a solid boat that I will rent again when in Annapolis. The engine and navigation display are brand new and made for a smooth ride for my family of 4. The boat could comfortably fit 6 adults, so we had lots of room. Controls were simple and handling easy. Great way to see the Academy from the water. When I asked my wife and sons what their highlight of our DC vacation was, they all said "the boat ride"! William the owner was right on time for pickup and drop off, and even gave us a great crabcake restaurant recommendation!
AC
Allison
Just Repowered Cuddy Cabin/Walk Around bareboat fishing charter in Annapolis
We had a great day on the Bay thanks to Will. He was very communicative and made the hand-offs getting/returning the boat very easy. The boat was clean, easy to operate, perfect for fishing or just spending some time on the water. We would definitely recommend Will to friends and hope to go fishing again sometime soon!
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!