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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
Miami, Florida
903 boats to rent
Cancún, Quintana Roo
615 boats to rent
Isla Mujeres, Quintana Roo
464 boats to rent
Tampa, Florida
418 boats to rent
Miami Beach, Florida
387 boats to rent
Los Angeles, California
368 boats to rent
Lake Michigan, United States
364 boats to rent
Cabo San Lucas, Baja California Sur
313 boats to rent
Puerto Vallarta, Jalisco
284 boats to rent
Chicago, Illinois
281 boats to rent
Marina, Cabo San Lucas
277 boats to rent
Nuevo Vallarta, Nayarit
262 boats to rent
Fort Lauderdale, Florida
262 boats to rent
Saint Petersburg, Florida
258 boats to rent
Hollywood, Florida
247 boats to rent
Dania Beach, Florida
240 boats to rent
Punta Cana, La Altagracia
235 boats to rent
Cartagena, Bolivar
235 boats to rent
Most Popular Pontoon Rentals Near Me
Recent Reviews Near Me
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.
Brittany
Charter this beautiful Catalina from Milwaukee, WI - Captain Included
Patrik was so kind! We absolutely loved our sunset cruise around Milwaukee. He was so friendly and had great areas to go by! We loved every part of our engagement session and can’t think of a better skipper 🥰
CS
Corrie
41ft Sailing Crusing Monohull Charter on ''White Lake'' Michigan, USA.
John recently took my family out on Lake Michigan and he made the trip a great experience - communicative, nicely kept boat and very competent as a captain! I appreciated how he answered my youngest questions and was so thoughtful with them. Would recommend.
MJ
Meneka
Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois
Sailing with Nijole and her husband was an incredible experience! From the start, they were very responsive in communication and flexible with our requested times, even allowing us to extend once on the water. Their knowledge, warmth, and passion for sailing made the trip both safe and fun, with stunning views that we’ll never forget. Highly recommend!
Van A.
Charter this beautiful Catalina from Milwaukee, WI - Captain Included
A great Milwaukee skyline sail with an old sailor and his 8 and 5 year old grandkids. Patrick was totally accommodating and I was very happy. Toby “loved the ride” And Betty feigned boredom. I know they both loved the experience. Patrick our skipper was great. The boat clean and well cared for.
Top Sailboat Rental Locations in the United States
Los Angeles, California
368 boats to rent
Marina del Rey, California
133 boats to rent
Miami, Florida
903 boats to rent
San Francisco, California
69 boats to rent
Honolulu, Hawaii
58 boats to rent
New York, New York
90 boats to rent
Oakland, California
39 boats to rent
Annapolis, Maryland
51 boats to rent
San Diego, California
97 boats to rent
Newport Beach, California
132 boats to rent
Charleston, South Carolina
117 boats to rent
Baltimore, Maryland
45 boats to rent
Dania Beach, Florida
240 boats to rent
Chicago, Illinois
281 boats to rent
Fort Lauderdale, Florida
262 boats to rent
Southampton, New York
72 boats to rent
Hitchcock, Texas
54 boats to rent
Noyack, New York
46 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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