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

870 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 - 30 of 12,088 listings
hour$100
Florida
10 guests

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

hour$180
Illinois
6 guests

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

hour$84
Florida
6 guests

Cruising Catamaran rental in Jacksonville, Florida

hour$650
California
27 guests

55' Luxury Sail Yacht for up to 27 People!

hour$325
California
12 guests

Beautiful 46' Benetau Sail Boat

hour$110
Maryland
6 guests

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

hour$250
California
6 guests

49' Hunter Sloop "Belle Colette" Charter in Alameda

hour$150
California
6 guests

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

hour$199
California
12 guests

Sailing catamaran ideal for parties/event - NEW SUNSET CRUISES

hour$70
Baja California Sur
8 guests

Classic Ketch Sailing tours La Paz (no bareboat)

hour$97
Lisboa
6 guests

Private Sail along the Tagus River (34ft)

night$268
Catalunya
4 guests

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

hour$248
Florida
12 guests

CATVIAR! 35 Foot Sailing Catamaran In Miami!

hour$160
Quintana Roo
25 guests

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

day$1,600
Bolívar
25 guests

Captained Charter on Lagoon 440 Cruising Catamaran in Cartagena, Bolivar

hour$125
California
6 guests

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

person$75
Río Negro
12 guests

Charter a Cruising Monohull in Bariloche, Argentina

hour$154
Reykjavík
8 guests

Sailing Charter 35ft "Wild Geese" Cruising Monohull In Reykjavík, Iceland

hour$201
Victoria
9 guests

Rent Catalina 320 Cruising Monohull in Docklands, Victoria

day$513
Barcelona
4 guests

41ft Dufour Daysailer Boat Rental in Barcelona, Spain

hour$131
Lisboa
10 guests

Private Sail along the Tagus River (40ft)

hour$134
Humacao
6 guests

Elegant Hinckley Sou'wester 59 sloop in the Caribbean

hour$98
Quintana Roo
13 guests

Enjoy the 32' Sailing Catamaran in Cancún, Quintana Roo

hour$135
South District
10 guests

Charter Tamara Cruising Monohull in Ashkelon, Israel

person$150
Bay Islands Department
6 guests

Charter 39' Oceanis 393 Cruising Monohull in Roatan, Honduras

hour$299
Quintana Roo
15 guests

36' Cruising Catamaran Charter in Quintana Roo, Mexico

hour$350
Hawaii
12 guests

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

day$950
Maputo
12 guests

Charter Leopard 40 Cruising Catamaran in Maputo, Mozambique

hour$114
Larnaca
8 guests

Sailing Cruising Monohull Rental in Larnaca and Nicosia, Cyprus

hour$163
Jalisco
10 guests

Enjoy "Obsession". Hunter 38 Sailboat in Puerto Vallarta, Jalisco

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