Find awesome sailboat rentals and sailing charters for any travel destination.

889 reviews worldwide.

Set sail with the best sailboat rentals and charters around the world.

Hit the open water in style on a sailboat rental or sailing charter. You can rent or charter a sailboat with or without a captain. Enjoy exploring the water by wind power. Most larger sailboats (typically 18+ feet) also use an engine for longer sailing trips. From hourly, half-day, full-day or multi-day sailing excursions, you are sure to create memories that will last a lifetime.

Using GetMyBoat to rent your next sailboat.

Experiencing the water has never been easier thanks to GetMyBoat. GetMyBoat allows you to quickly search, compare prices, submit rental inquiries, and pay for your rental or charter from the convenience of your phone or computer. We offer a secure platform for renters to facilitate a seamless rental transaction. For boat owners, we connect millions of renters to their boat and provide the security and safety checks on each rental transaction.

Search for the perfect experience now and book your dream day out on the water.

Things to consider when booking a sailboat rental or charter.

  • Sailboats range in size and carrying capacity, so check with the captain to make sure the boat you pick will meet your needs.
  • If you want to learn some sailing techniques, ask about instruction or lessons while you're onboard.
  • Any doubts about booking your sailing adventure? No problem! Simply message the captain and ask any questions you may have.
1 - 18 of 12,024 listings
hourCA$132
Florida
10 guests

Sailing Charter On 39' Catalina Sailboat In Fort Lauderdale, Florida

hourCA$237
Illinois
6 guests

Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois

hourCA$111
Florida
6 guests

Cruising Catamaran rental in Jacksonville, Florida

hourCA$857
California
27 guests

55' Luxury Sail Yacht for up to 27 People!

hourCA$145
Maryland
6 guests

Carefree Tours with Homegrown Captain on 38' Sailboat in Galesville, Maryland (West River, Chesapeake Bay)

hourCA$330
California
6 guests

49' Hunter Sloop "Belle Colette" Charter in Alameda

hourCA$198
California
6 guests

"Wild Streak" 36' Catalina Sloop Charter in Sausalito, California

hourCA$262
California
12 guests

Sailing catamaran ideal for parties/event - NEW SUNSET CRUISES

hourCA$211
Quintana Roo
25 guests

Charter this 37ft ft Cruising Catamaran for a Boat Party in Cancún, Quintana Roo

dayCA$2,110
Bolívar
25 guests

Captained Charter on Lagoon 440 Cruising Catamaran in Cartagena, Bolivar

hourCA$92
Baja California Sur
8 guests

Classic Ketch Sailing tours La Paz (no bareboat)

hourCA$165
California
6 guests

Sailing Charters On 36ft "Breath of an Angel" Cruising Monohull In Oceanside, California

hourCA$127
Lisboa
6 guests

Private Sail along the Tagus River (34ft)

nightCA$352
Catalunya
4 guests

41ft Dufour Daysailer Boat Sleep Aboard Rental in Barcelona, Spain

hourCA$327
Florida
12 guests

CATVIAR! 35 Foot Sailing Catamaran In Miami!

hourCA$129
Quintana Roo
13 guests

Enjoy the 32' Sailing Catamaran in Cancún, Quintana Roo

hourCA$462
Hawaii
12 guests

Sailing Charter On 48' Custom Made Sailing Catamaran In Honolulu, Hawaii

hourCA$224
Barcelona
10 guests

Sailing experience Barcelona: Sunset, Sunrise, Midday and Full Day Cruises

12,000+ results