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Fishing Charters
Let a captain do the driving while you do the fishing
$95-$725
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$95-$725
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$45-$200
Sailboats
Set sail with these traditional wind-powered boats
$100-$725
Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$95-$200
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$300-$450
Wakeboarding Boats
A high-octane powerboat designed and outfitted for wakeboard towing
$150
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Hadiya
Beautiful Chaparral 35ft Cruiser for rent in Washington, D.C.
We had the most amazing time celebrating my birthday with Captain Troy. He is accommodating, kind, and very responsive, making the entire planning process seamless and stress-free. Captain created the best environment for us to be able to have fun and enjoy our charter. Will absolutely recommend and will book again!
UU
Uche
Fun family time Jet Ski Rentals at Lake Norman, NC
Breyanna was very good with communicating instructions and prioritizing safety. She was also flexible with scheduling and wanted us to have the best experience by providing alternative times when weather proved unstable.
WB
Winnie
Captain Bill invites you to find your Sailing Dream on Chesapeake Bay.
Capt. Bill was so accommodating and great with his communication. We had an emergency and he was very understanding. He gave my nine year old great information about the boat and the waters. He and Jonathan were very kind during our charter. It was a great first sail for our family!
AH
Angela
Captain Bill invites you to find your Sailing Dream on Chesapeake Bay.
Captain Bill was absolutely marvelous!! The trip was amazing!! My guest and I chartered a three hour venture and had the wonderful adventure! We celebrated my cousin’s birthday and everyone was elated to ride with such a great captain! He went above and beyond to make sure we had a joyous occasion! His personality was second to none!! I extremely recommend you charter him for your next boat ride!! You will not be disappointed!!
NC
Nick
Captain Bill invites you to find your Sailing Dream on Chesapeake Bay.
Bill was terrific at helping me learn more about handling a 42' sailboat. I'm trying to get more experience in preparation for taking a bareboat charter, and Bill's experience and mentorship was terrific. I look forward to booking with Bill again in the future.
Michael
Captain Bill invites you to find your Sailing Dream on Chesapeake Bay.
Captain Bill offers the best value boat charter in the annapolis area, in my opinion. My wife and I chartered captain bills boat (through getmyboat.com) to celebrate her birthday and we had a wonderful time. You can participate as much or as little in the actual sailing as you prefer. There are several comfortable areas on the deck to lounge and catch some cosmic rays, and a salon below deck if you need to beat the heat. BYOB, BYO-snacks, bill provides the ice, water, coozies, and jokes. Very fun charter, would recommend to a friend
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!