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Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$185-$640
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$150-$450
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$95-$840
Fishing Charters
Let a captain do the driving while you do the fishing
$95-$840
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$150-$400
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$95-$150
Wakeboarding Boats
A high-octane powerboat designed and outfitted for wakeboard towing
$200
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!!!!!!
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!
RH
Roger
Sailing Adventure in Chesapeake Bay with 28ft Tartan Sailing Yacht!
Great vessel. Well maintained. Up to date equipment. Very relaxed.
Ben
41' Lagoon Catamaran in Maryland
Jess was a great captain! We hosted my wife’s 30th birthday party with Jess and it was a great time! His catamaran fit all 12 of us with no problem. He was attentive to the things she wanted to do and was knowledgeable about the area. We had a awesome day on the water with Captain Jess. Would definitely go again!
Alex
41' Lagoon Catamaran in Maryland
Jess was an amazing captain with a gorgeous boat. We had a group of ten women and Jess was so friendly but also gave us our privacy. He offered to take us swimming, but we opted to ride along the bay instead. While it’s an expensive excursion, it’s worth every penny and I will definitely reach out to jess again in the future. I highly recommend!!
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!
August 01, 2023
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October 03, 2022
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August 12, 2021
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July 19, 2021
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December 30, 2019
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December 26, 2019
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