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The Best Cruising Catamaran 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
Sailboats
Set sail with these traditional wind-powered boats
$90-$1,065
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$35-$300
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$85-$755
Fishing Charters
Let a captain do the driving while you do the fishing
$60-$725
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$55-$470
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!
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!
Danika
Charter 44' Orana Cruising Catamaran In Deale, Maryland
We had the best time! Everything was perfect! Rob communicated well! The boat looked exactly like the pictures. It was enough space for my 10 guest party! We sailed out for 7hrs and it still didn’t feel like enough time! I’m so glad I went with this boat and will be using it again in the future. Best birthday ever!!!
JH
Jennifer
Charter 44' Orana Cruising Catamaran In Deale, Maryland
Rob was so communicative and helpful throughout the entire booking process, and our experience on the boat was even better! Not only was it a beautifully appointed vessel, but our captain Adam took such wonderful care of our group. We can never outdo this day-- just plan when we can do it again!
CE
Clifford
SWEET & SALTY FOUNTAINE PAJOT HELIA 44 CATAMARAN
Sarah was helpful in lining me up for a sail boat for Mothers Day and in recommending a captain and in adjusting time to meet our needs.
SH
Sophia
Charter 44' Orana Cruising Catamaran In Deale, Maryland
This trip was above and beyond ! The boat is spacious, beautiful, and comfortable. Everything was seamless and we spent a wonderful time sailing, swimming, and relaxing on the various parts of the boat.
Top Cruising Catamaran 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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