Cookies!
We use cookies to improve your browsing experience. By continuing to browse or closing this banner, you agree to our use of cookies. Find out more about our cookies policy here.
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
912 boats to rent
Cancún, Quintana Roo
622 boats to rent
Isla Mujeres, Quintana Roo
468 boats to rent
Tampa, Florida
422 boats to rent
Miami Beach, Florida
394 boats to rent
Los Angeles, California
376 boats to rent
Lake Michigan, United States
370 boats to rent
Cabo San Lucas, Baja California Sur
292 boats to rent
Puerto Vallarta, Jalisco
288 boats to rent
Chicago, Illinois
281 boats to rent
Fort Lauderdale, Florida
269 boats to rent
Nuevo Vallarta, Nayarit
264 boats to rent
Saint Petersburg, Florida
261 boats to rent
Marina, Cabo San Lucas
257 boats to rent
Hollywood, Florida
256 boats to rent
Dania Beach, Florida
247 boats to rent
Punta Cana, La Altagracia
236 boats to rent
Clearwater, Florida
235 boats to rent
Most Popular Pontoon Rentals Near Me
Recent Reviews Near Me
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.
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 🥰
Top Sailboat Rental Locations in the United States
Los Angeles, California
376 boats to rent
Marina del Rey, California
136 boats to rent
Miami, Florida
912 boats to rent
San Francisco, California
72 boats to rent
Honolulu, Hawaii
58 boats to rent
New York, New York
90 boats to rent
Oakland, California
40 boats to rent
Annapolis, Maryland
49 boats to rent
San Diego, California
101 boats to rent
Newport Beach, California
134 boats to rent
Charleston, South Carolina
118 boats to rent
Chicago, Illinois
281 boats to rent
Baltimore, Maryland
43 boats to rent
Dania Beach, Florida
247 boats to rent
Palm Beach, Florida
127 boats to rent
Southampton, New York
67 boats to rent
Hitchcock, Texas
55 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!
Dive into Our Journal
August 01, 2023
10 Boating Adventures of a Lifetime
Read Article
October 03, 2022
Getmyboat's Guides to the World of Boating
Read Article
August 12, 2021
Caribbean Flavors on the Water in NYC - Book an Anchored & Chef'd Catered Cruise with Getmyboat!
Read Article
July 19, 2021
Sailing Charters on Lake Tahoe | Getmyboat
Read Article
December 30, 2019
South Africa Boating & Watersports Guide - Getmyboat
Read Article
December 26, 2019
Complete Fishing Guide to Southern California - GetMyBoat
Read Article
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.
Real reviews from happy Getmyboaters.
4.9 out of 5! 500,000+ reviews
