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The Best Sailboat Rentals Near Me
Browse, book, and get out onto the water with local captains and boat owners.
Suggested Searches
Types of Boats Popular Near Me
Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$190-$970
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$180-$1,150
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$175-$415
Fishing Charters
Let a captain do the driving while you do the fishing
$90-$330
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$90-$335
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$105-$190
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$230-$1,070
Kayaks
Who says you need a motor to have fun on the water?
$200
Wakeboarding Boats
A high-octane powerboat designed and outfitted for wakeboard towing
$350
Top Sailboat Rental Locations Near Me
Arlington, Virginia
31 boats to rent
Washington, District of Columbia
120 boats to rent
Potomac River, United States
165 boats to rent
Oxon Hill, Maryland
8 boats to rent
Fort Washington, Maryland
14 boats to rent
Baltimore, Maryland
50 boats to rent
Selby-on-the-Bay, Maryland
7 boats to rent
Annapolis, Maryland
52 boats to rent
Lake Anna, Virginia
8 boats to rent
Richmond, Virginia
7 boats to rent
Chesapeake Bay, United States
209 boats to rent
Cape May, New Jersey
9 boats to rent
Wildwood, New Jersey
9 boats to rent
Chesapeake, Virginia
28 boats to rent
Virginia Beach, Virginia
17 boats to rent
Lake Gaston, United States
7 boats to rent
Long Beach Island, New Jersey
8 boats to rent
Toms River, New Jersey
18 boats to rent
Recent Reviews Near Me
LF
Linda
Private Annapolis Sailing Experience on a Classic 37' Nauticat Ketch
Stephen was wonderful! A few days before our sailing trip, the weather forecast looked questionable, but he stayed in touch the entire time, offering to start earlier or even reschedule for a different day if needed. He was incredibly flexible and genuinely wanted to make sure we had the best possible experience. Thanks to his communication and commitment, we had a fantastic trip. I highly recommend sailing with Stephen!
RM
Richard
38-ft Hunter 376 Sailing Adventure in Annapolis
Capt. Alberto and his wife were awesome hosts! They were totally flexible about our schedule and it was great to hear about his prior sailing experiences. It was great to be with such an experienced host! We will definitely book with them in the future!!
MK
Michael
38-ft Hunter 376 Sailing Adventure in Annapolis
Capt Alberto is great. Very knowledgeable and very pleasant. He lets you participate in manning the boat as much as you want and is especially good and introducing new sailors to the glorious activity. Highly recommend!
JK
Junghun Jemma
Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours
With Ian, our special 250th July 4th celebration became even more unforgettable. From the marina, we enjoyed spectacular views of the fireworks. What made the evening truly exceptional was Ian's personalized dock tour—something only possible because of his close relationship with the marina. It gave us experiences we never expected, including seeing the historic tall ships, watching the special boats on the river, and getting a close look at the Macy's fireworks barges as they prepared for the show. Ian went out of his way to make sure our family had a remarkable experience. Seeing my granddaughter dancing on the deck of his romantic sailboat to the music Ian thoughtfully selected, with the fireworks lighting up the sky in front of her, is a memory we will cherish forever. Thank you, Ian, for making our Independence Day celebration so magical. We will definitely be back on your sailboat for another special occasion soon!
MB
Maya
38-ft Hunter 376 Sailing Adventure in Annapolis
Capt Alberto and his wife were SO AMAZING!! They taught us how to sail and we sailed across the Chesapeake. Their boat is beautiful and their company is great. I highly recommend everyone book if they are looking to sail in the Annapolis area for a few hours, learn about sailing, and have a relaxing time.
Cindy
38-ft Hunter 376 Sailing Adventure in Annapolis
We had a wonderful time on the water with Captain Alberto and Grace! Their wealth of sailing knowledge of the bay and beyond was quite entertaining and impressive. Thanks for sharing your lovely boat with us.
Top Sailboat Rental Locations in the United States
Los Angeles, California
355 boats to rent
San Francisco, California
82 boats to rent
Oakland, California
47 boats to rent
Marina del Rey, California
124 boats to rent
Honolulu, Hawaii
42 boats to rent
Miami, Florida
783 boats to rent
San Diego, California
106 boats to rent
New York, New York
81 boats to rent
Annapolis, Maryland
52 boats to rent
Hitchcock, Texas
54 boats to rent
Texas City, Texas
44 boats to rent
Chicago, Illinois
288 boats to rent
Charleston, South Carolina
126 boats to rent
Houston, Texas
53 boats to rent
Kemah, Texas
44 boats to rent
Clear Lake Shores, Texas
41 boats to rent
Baltimore, Maryland
50 boats to rent
Tampa, Florida
383 boats to rent
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
What types of sailboats can I rent?
You can rent a wide range of sailboats including small day sailors, catamarans, sloops, and luxury sailing yachts. Options vary by location and skill level.
Do I need sailing experience to rent a sailboat?
Not always. If you’re an experienced sailor, you can book a bareboat rental in many locations. Otherwise, you can hire a captained sailboat where a licensed skipper handles navigation and safety.
How much does it cost to rent a sailboat?
Costs depend on the boat size, location, and whether it's captained or bareboat. Small sailboats start around $100–$300 per day, while larger or luxury sailboats can range from $500 to $2,000+ per day.
What’s the difference between a captained and bareboat sailboat rental?
A captained rental includes a professional skipper who handles the sailing. A bareboat rental means you're responsible for sailing the vessel yourself and usually requires proof of sailing experience or certification.
How long can I rent a sailboat for?
Sailboat rentals are available by the hour, for a full day, or for multi-day charters. Multi-day charters are popular for exploring coastal destinations or island-hopping.
Can I go overnight or on multi-day trips with a sailboat rental?
Yes, many sailboats are equipped for overnight charters with cabins, bathrooms, and kitchens. Check listings for sleeping capacity and amenities before booking.
What should I bring on a sailboat trip?
Bring sunscreen, sunglasses, a hat, non-slip shoes, layered clothing, and snacks or drinks if not provided. If you're staying overnight, pack light and bring essentials like toiletries and swimwear.
Are sailboat rentals suitable for beginners?
Yes, with a captain on board. If you're new to sailing, booking a captained charter is a great way to learn the ropes or simply relax while someone else navigates.
Can I book a sailboat for a special event?
Absolutely. Sailboats are a unique choice for proposals, anniversaries, sunset cruises, team outings, and small celebrations. Be sure to mention the occasion when booking.
What happens if the weather is bad on the day of my rental?
If conditions are unsafe, most operators will reschedule or offer a refund. Light wind or overcast skies may not cancel a booking, but safety is always the priority.
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