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Sailboats
Set sail with these traditional wind-powered boats
$85-$1,865
Fishing Charters
Let a captain do the driving while you do the fishing
$95-$350
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$175-$400
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$95-$350
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
Noelle
Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways
My group and I had an amazing time! If you’re looking to have a great experience make sure to book with Captain McCoy. The boat was very clean. Getting on board was simple and finding the dock was easy. Also enjoyed stopping in the middle of our trip to just enjoy the weather and laying out on the front of the boat. I’d definitely book again!
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!
LW
Lianna
Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways
Captain McCoy was wonderful! Very accommodating and communicative. Our group had a great time!
KC
Kevin
41' Lagoon Catamaran in Maryland
Captain Jess was fantastic! Great experience!
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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December 11, 2019
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August 24, 2023
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April 10, 2020
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December 30, 2019
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