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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
Top Sailboat Rental Locations Near Me
Detroit, Michigan
32 boats to rent
Saint Clair Shores, Michigan
20 boats to rent
Holland, Michigan
7 boats to rent
Norris Lake, Tennessee
13 boats to rent
Chicago, Illinois
281 boats to rent
Knoxville, Tennessee
10 boats to rent
Mississauga, Ontario
67 boats to rent
Lake Anna, Virginia
10 boats to rent
Old Hickory Lake, Tennessee
16 boats to rent
Toronto, Ontario
59 boats to rent
Hendersonville, Tennessee
16 boats to rent
Potomac River, United States
176 boats to rent
Lake Norman of Catawba, North Carolina
39 boats to rent
Arlington, Virginia
28 boats to rent
Lake Michigan, United States
370 boats to rent
Mooresville, North Carolina
12 boats to rent
Washington, District of Columbia
110 boats to rent
Percy Priest Lake, Nashville
14 boats to rent
Most Popular Pontoon Rentals Near Me
Recent Reviews Near Me
ML
Martha
50ft Catamaran Charter with Water Toys - Annapolis, MD
We intentionally booked a late afternoon cruise around the Chesapeake so we would return around sunset to get great views and photos. Kristal was super responsive in preparing us and Captain Wayne and his 'first mate' Mish were super helpful with capturing the perfect photos. We would definitely book again!
CM
Caley
Beautiful Ranger 22 Sailboat for rent in Chicago Monroe Harbor
Amazing time! Ben is a very experienced and knowledgeable captain , he taught us how to steer the boat and answered all our questions. Hes very nice and made the ride great! You also get an amazing view of the city that you can’t get anywhere else I brought my boyfriend as a birthday present and it was perfect!
Ben
Beautiful Ranger 22 Sailboat for rent in Chicago Monroe Harbor
Ben was an awesome captain and a pleasure to be around during our two-hour trip. His boat is the perfect setting for a romantic date night, and I highly recommend experiencing the sunset on board, the views were absolutely amazing!
AP
Andrea
38-ft Hunter 376 Sailing Adventure in Annapolis
This was our crew’s second trip with Capt Alberto and was a second great experience. Capt Alberto shares his passion for sailing and teaching sailing! Capt and Grace are incredibly kind and make a great day spent out on the bay!
Elisabeth
Come Aboard and Sail Optimystic-Experience the breeze w/Lunch, Wine and Cheese
Charles & Renee were amazing! We booked last minute and enjoyed an awesome afternoon on The Optimystic in Chesapeake Bay!! We can’t wait to sail again!! Charles is an excellent Captain and host. A good teacher as well! Have an awesome winter!! See you in the Spring!! Charlie, Beth and Sam (Class of 2026) ⚓️⚓️⚓️
Lisa
38-ft Hunter 376 Sailing Adventure in Annapolis
Thank you so much Captain Alberto & Grace. We had a fabulous time and enjoyed learning about sailing. Thanks for trusting us to help steer and tack the boat. We had so much fun. You are a great teacher. We wish we could have stayed out longer.
Top Sailboat Rental Locations in the United States
Los Angeles, California
376 boats to rent
San Francisco, California
74 boats to rent
Marina del Rey, California
137 boats to rent
Miami, Florida
916 boats to rent
Honolulu, Hawaii
57 boats to rent
Oakland, California
42 boats to rent
New York, New York
87 boats to rent
Annapolis, Maryland
50 boats to rent
San Diego, California
97 boats to rent
Charleston, South Carolina
120 boats to rent
Baltimore, Maryland
45 boats to rent
Newport Beach, California
132 boats to rent
Chicago, Illinois
281 boats to rent
Texas City, Texas
38 boats to rent
Hitchcock, Texas
56 boats to rent
Dania Beach, Florida
249 boats to rent
Palm Beach, Florida
127 boats to rent
Riviera Beach, Florida
122 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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