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The Best Sailboat Rentals in Chesapeake Bay
Browse, book, and get out onto the water with local captains and boat owners.
Suggested Searches
Types of Boats Popular in Chesapeake Bay
Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$110-$610
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$85-$755
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$55-$470
Fishing Charters
Let a captain do the driving while you do the fishing
$60-$725
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$35-$300
Kayaks
Who says you need a motor to have fun on the water?
$80-$450
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$80-$400
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$95-$350
Whale Watching
See some of the ocean’s most incredible creatures with these eco tours
$60
Wakeboarding Boats
A high-octane powerboat designed and outfitted for wakeboard towing
$150
Recent Reviews in Chesapeake Bay
DC
Donte
New Yacht Charter Bali 5.4 Sailing Catamaran in Annapolis Maryland
From start to finish, the entire experience was seamless and professional. There was zero chaos—everything ran like clockwork. The crew was exceptional: friendly, attentive, and incredibly knowledgeable about the Chesapeake Bay and Annapolis. The yacht itself was spotless and in pristine condition. From the moment we arrived, the crew went above and beyond—helping us load in, beautifully setting up our catering, keeping our group refreshed with drinks and snacks, and later packing up leftovers and loading them into our car. Every detail was handled with care. If you’re considering a yacht rental, don’t hesitate—this experience was truly top-notch. We’re already looking forward to booking again!
Marie
38-ft Hunter 376 Sailing Adventure in Annapolis
We thoroughly enjoyed our time with Alberto and his wife, Grace. Alberto is a delight to sail with - we learned so much from him. Grace is so lovely and gracious. We sailed around Annapolis during Memorial Day weekend and the weather was perfect. Alberto was very accommodating and friendly. We hope to see you again soon!
Sam
38-ft Hunter 376 Sailing Adventure in Annapolis
Captain Alberto is a wonderful Captain. Handles the boat with an expert confidence and was also a willing and kind teacher to my two kids who had millions of questions.
GQ
Gin
Come Experience the ambient waters of the Potomac on the Sylvan MIRAGE Pontoon!
Was an incredible, beautiful, and relaxing trip on the water. Demi is a wonderful and chill captain and knows all the best spots in the area and I'd defiantly take another trip with him again!
MR
Matt
STARZ -Lagoon 42 Catamaran in Chesapeake Bay
Great experience and our family and friends had a wonderful time. Clean boat and fun crew to help us celebrate a special occasion. Highly recommend!
hg
hunter
Captain Bill invites you to find your Sailing Dream on Chesapeake Bay.
we did our engagement pictures on the boat & everything was great! Bill was super cooperative & made sure we got all of the best spots for pictures! highly recommend!
Top Sailboat Rental Locations in the United States
How To Book on Getmyboat
Browse
Find the right listing for you and your crew, with options for boat types, group size, captained or self-charter, and lots more.
Inquire & Book
Found one you like? Send a rental inquiry with your preferred trip details, and you’ll receive an offer from your captain to book.
Enjoy
Coordinate a pick-up place and time, meet your boat captain, and get out onto the water!
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