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Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$150-$600
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$50-$500
Fishing Charters
Let a captain do the driving while you do the fishing
$50-$725
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$55-$740
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$40-$475
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$50-$485
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$95-$350
Wakeboarding Boats
A high-octane powerboat designed and outfitted for wakeboard towing
$190-$200
Rafting
A high-energy adventure for the whole family
$130
CB
Caprice
41' Lagoon Catamaran in Maryland
This was one of the best rides I’ve had in a while. Captain Jess is communicative, helpful and kind. We went out for 4 hours and had great weather. The boat is clean, he had 2 fridges for our food and drinks, it was nice and spacious, and there were floaties to get out on the water. It was a very enjoyable day.
DB
Dan
38' Hunter 376 Cruising Monohull in Annapolis, Maryland
Capt Alberto and Grace were wonderful hosts. They were very flexible regarding the weather, great teachers of sailing, and were very hospitable and welcoming with their boat. We had an amazing time. Capt Alberto truly loves the sea.
NW
Nicole
Luxury Sailing Catamaran ⭐️⭐️⭐️⭐️⭐️
I hosted my 50th birthday on this vessel!! Absolutely, positively an amazing experience! The vessel is absolutely beautiful and spacious. There was plenty of room on this vessel for my 12 guests! The Captain Shane provided excellent customer service throughout the entire trip. He very responsive to any questions that I had !!! If you want an stellar experience, this is the way to go!!!!!!
bb
brent
41' Lagoon Catamaran in Maryland
Captain J was excellent. So nice and accommodating to our requests. It is our second time with him and will book with him again next time we want to have a great day on the water
PG
Polina
38' Hunter 376 Cruising Monohull in Annapolis, Maryland
Thanks to captain Alberto and Grace my birthday became unforgettable! Completely met all our expectations.!
KC
Kevin
Charter 42' Lagoon Catamaran in Annapolis, MD
Adam Yearwood is a fantastic captain! His boat is beautiful and he is well organized. We did a team outing sailing around the Chesapeake and had an awesome time - I highly recommend working with Adam!
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!
April 17, 2024
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December 30, 2019
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December 19, 2019
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August 01, 2023
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October 03, 2022
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August 12, 2021
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