Choosing a sailboat charter for a sailing vacation in the Caribbean Islands? Enjoy a one-of-a kind experience on the water with your own private sailboat rental in Caribbean with Sailo! Whatever your sailing style; from experienced skipper, fishing fanatic or thrill seeker, to those who just want to relax on deck with your family or friends, you’ll be spoiled for choice. Rent a sailboat in Caribbean with Sailo for a memorable day trip or a sailing vacation to remember.

The best Caribbean private sailboat charters available on Sailo

Caribbean by a sailboat rental is the perfect destination to explore from Sailo! Following a thorough vetting process, we offer a total of 1553 charters in this location, available with or without captain. Take your family or friends on an amazing trip in Caribbean to enjoy the coastal landscape or watch a sunset, practice watersports, go fishing or simply relax and make the best of your staying outdoors.

How to find the ideal Caribbean sailboat rental for unforgettable yachting experiences

Sailo offers beautiful sailboat rentals in Caribbean at various price points. Use our advanced filters to narrow your search by date, group size, and trip duration: 2 hrs, 4 hrs or full day charters. You can also choose the type of boat (sailboat, motorboat, catamaran) you want and go even further and look for a particular length, manufacturer and model. The price filter will help you see the available boats within your budget and the crew option is useful when you want to see boats with a skipper/captain included or only bareboats. Do you see a sailboat to rent in Caribbean that you would like? Click on it to go to the next page to read more about it, see more photos, send a direct message to the owner to ask more questions or start creating your booking request right away!

How much does it cost to rent a sailing charter in Caribbean?

You can charter a sailboat in the Caribbean Islands for a day, for an average of $1100. The average price for a weekly sailboat rental in Caribbean region is $13930. Your total budget for a sailing trip in Caribbean depends on many factors such as: trip duration, if captain and crew are included in the price or their cost have to be paid separately, fuel cost (which could be significantly higher on a motorboat compared to a sailboat) and other extras you choose to customize your experience in Caribbean.

What is Sailo FREE 24 hours Reservation?

Not sure if the boat you like suits your Caribbean sailing vacation plans? You can place a free reservation for 24 hrs, no credit card required, for most of our weekly boat rentals, allowing you more time to discuss details with the boat owner, talk to your family or friends or customize your budget to suit your needs. Once you have placed the reservation, boat is blocked for 24 hours. During the 24 hours of your reservation, you can book the boat, cancel the reservation or ask for a one-time extension of 24 hours by contacting us at reserve@sailo.com. If you do nothing, your reservation will automatically expire and the boat will become available for other renters. Read more about free reservations.

Guidelines to responsible yachting

If you’re looking to explore our beautiful planet, a Caribbean sailboat charter is a great place to start. Explore coral reefs with your snorkel, discover hidden bays and islands and generally enjoy the view of nature. Remember, that sailing motto: 'Take only photos, leave only wake' (OK, so we paraphrased). To be a responsible sailor, remember:

Don’t disturb coral or sealife
Take your trash home (and don’t throw anything in the sea)
Respect the locals and their customs wherever you go

Popular locations for renting the Caribbean yacht charters :

Popular boat types among renters in the Caribbean Islands:

Caribbean catamaran charters
BVI catamaran charters
Sailboat charters in BVI
Catamaran rentals in St. Thomas
U.S. Virgin Islands sailboat charters
USVI catamaran charters
Tortola catamaran rentals & charters
Tortola sailing charters
BVI motor yacht charters