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The Best Boat Rentals in Annapolis
Browse, book, and get out onto the water with local captains and boat owners.
Suggested Searches
Types of Boats Popular in Annapolis
Sailboats
Set sail with these traditional wind-powered boats
$140-$1,775
Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$205-$1,925
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$175-$450
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-$450
Fishing Charters
Let a captain do the driving while you do the fishing
$95-$350
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$95-$350
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$95-$150
Top Boat Rental Locations Near Annapolis
Recent Reviews in Annapolis
BF
Bruce
38' Hunter 376 Cruising Monohull in Annapolis, Maryland
Our family of four, who are experienced sailors, appreciated the opportunity to sail with Alberto and his lovely wife, who shared lots of great stories and reflections of sailing on the Bay. The boat was perfect for a day of sailing, and exactly how described on the website. It was clean and comfortable and we felt completely welcomed, and were able to participate in sailing activities as we desired, while also relaxing and enjoying some downtime. Great time sailing!
George
Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland
HIGHLY recommend Capt Joe for a fantastic sailing experience out of Rock Hall. Joe worked with us to get a last-minute booking when another booking fell through. He and his crew are experts and you will not be disappointed. He let us take the helm and participate as much or as little as we wanted to. Sol Searcher is a beautiful, well-equipped boat - plenty of comfort and speed (wind dependent of course.)
TM
Tom
38' Hunter 376 Cruising Monohull in Annapolis, Maryland
Captain Alberto and Grace were amazing, and helped with a very romantic sunset sail. The were ver gracious, accommodating, and knowledgeable. If we get the chance we will definitely come back and hire them again!
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.
AL
Ayodele
Enjoy a Day on the Bay and Cruise the South River
Alan was great from the start! Very communicative and accommodating. Booking process was smooth. Our ride was super relaxing as we all felt safe with Alan as our captain! He took great photos of us to capture the memories! 10/10 recommend! Thanks Alan ✨
Top Boat 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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Frequently Asked Questions
How much does it cost to rent a sailboat for a day in Annapolis?
Renting a sailboat for a day in Annapolis starts at $350 a day for an Oceanis Cruising Monohull and goes up to $2,100 a day for a Lagoon Cruising Catamaran.
How much does it cost to rent a boat for a week in Annapolis?
Renting a boat in Annapolis starts at $100 for a sailboat and goes up to $1,600 for a motor yacht rental.
Can you sail in Annapolis without a License?
No, you do not need a license to rent a boat or sail in Annapolis. With Getmyboat, you can rent a boat with a licensed captain to enjoy your time on the water. If you want to captain the boat yourself, you must, at the very least, have a Boating Safety Certificate. Be aware that owners will have a checkout process to test your competency with their boat, so if you question your ability, even if you have your boating safety certificate, it is best to go out with a captain.
When does the boating season start in Annapolis?
While boating season can vary a bit depending on the weather, it usually starts near the tail end of April and ends in September.
Real reviews from happy Getmyboaters.
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