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Sailboats
Set sail with these traditional wind-powered boats
$140-$1,925
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$175-$300
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$150-$400
Kayaks
Who says you need a motor to have fun on the water?
$425
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$150
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$350
Fishing Charters
Let a captain do the driving while you do the fishing
$350
EB
Ernest
Private Yacht Charter: On 40ft Regal Commodore
GREAT experience!!! Captain Dennis was terrific. He was professional, yet fun & extremely well prepared. The yacht was clean & well maintained with all the amenities that we could ask for. Our only regret is that we did not book a longer cruise on Seas the Day.
Abigail
Private Yacht Charter: On 40ft Regal Commodore
Captain Dennis was exceptional—punctual, professional, and allowed us to have a great time. The boat itself was in perfect condition, with all the necessary equipment and some luxurious extras, like the floating 🏝️, that made the day truly enjoyable. The excellent service and the beautiful setting made it an unforgettable birthday party. I highly recommend Captain Dennis for anyone looking to host a memorable and top-notch maritime event.
Jordan
50ft Catamaran Charter with Water Toys - Annapolis, MD
Captain Deren and the crew were amazing — they made my birthday so special. They were super accommodating the entire day for everyone! They were even kind enough to put up some birthday decorations for our group. I’m definitely going to be booking with Captain Deren again!
MT
Marija
Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways
We had a wonderful time at Captain McCoy’s boat. The boat is gorgeous, impeccably clean, and very spacious. The Captain played great music (we didn’t bring our own playlist). He found a great spot for our group to take a swim. It was a perfect balance of cruising and swimming and a perfect 2 hr cruise
TS
Tiffany
Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways
Took my husband on a surprise boat ride for his birthday and he loved it!! McCoy was great at communication when I had questions. He took us on a 2 hour boat ride and made the trip so enjoyable and relaxing!! He played music for us and took us to see some beautiful sights. I will definitely be booking all my boat rides with McCoy in the future!
SR
Sara
Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways
We had a great experience with Captain McCoy and his boat. He definitely went the extra mile and was easy to communicate with to set up our trip. We went out of City Dock and toured the coastline, saw Chesapeake Bay bridge and then tied up for some swimming. He had a great float for the kids, and he had some comfy seats for the front of the boat. The shaded table in the back was awesome. Would 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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