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The Best Sailboat Rentals in Windward Islands
Browse, book, and get out onto the water with local captains and boat owners.
Suggested Searches
Types of Boats Popular in Windward Islands
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$40-$185
Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$160-$1,195
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$180-$1,195
Diving
Explore the ocean depths with trained boat operators
$40-$185
Fishing Charters
Let a captain do the driving while you do the fishing
$180-$1,195
Whale Watching
See some of the ocean’s most incredible creatures with these eco tours
$100
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$150
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$120
Top Sailboat Rental Locations Near Windward Islands
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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