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Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$15-$250
Sailboats
Set sail with these traditional wind-powered boats
$15-$1,310
Fishing Charters
Let a captain do the driving while you do the fishing
$15-$1,915
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$15-$2,105
Kayaks
Who says you need a motor to have fun on the water?
$15-$670
Snorkeling
Get off the boat and into the water with offshore snorkeling trips
$10-$140
Diving
Explore the ocean depths with trained boat operators
$60-$160
Wakeboarding Boats
A high-octane powerboat designed and outfitted for wakeboard towing
$45-$95
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$250
Houseboats
All the comforts of home out on the water, for multi-day boat trips
$15
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Lewis
Charter Beneteau Oceanis 440 in Saint Lucia private sailing cruise
We chartered the boat for a party of 4 for a half day trip around the west coast of the island. Organising was smooth and Alessandro was helpful in providing us the best deal for our needs. When we arrived at the marina we met our skipper Boby. He allowed us to pick our own itinerary, and gave us some great suggestions. Boby was a great skipper who had lots of insight into the various allocations we would pass, and knew the best mooring spots to allow us to swim. Would definitely recommend to anyone hesitant about booking.
KM
Kelly
Full Day Boat Tour to Soufriere
Titus and Chris were AMAZING! We had the absolute best day focused around snorkeling and visiting beautiful beaches on the west coast. Even in a small portion of down pour the crew got us so quickly to a beautiful bar in Marigot bay. 10/10 experience, can’t recommend enough!
AG
Andre
46' Bertram in Port of Spain, Trinidad
This was a fantastic day on the water with a full 15 members in the group. The size of the boat was adequate for all of us, but I'd recommend a smaller group for a more intimate adventure. Depending on the direction of travel it can be pretty hot on the lower deck since the air flow is not through that region.
EH
Erin
Set Sail in Style on the Caribbean Seas, Charter Your Dream Yacht today
We had the best time on the vessel and with the crew. The sites were beautiful, the food was delicious and the crew were all very friendly. We highly recommend this to anyone visiting!!
Alexandra
Charter 42' Whistle Wind Motor Yacht in Port of Spain, Trinidad and Tobago
We had an amazing day with Ronnie! He’s a great captain, welcoming host and his yacht is wonderful. Communication and scheduling with Ronnie was a breeze as well. We had a perfect day exploring Trinidad. If his yacht is available, do no hesitate to book!!!
Ma Estela
Charter 42' Whistle Wind Motor Yacht in Port of Spain, Trinidad and Tobago
7 of my best girlfriends and I celebrated my bachelorette in Trinidad. We had the honor of having Ronald as our beloved captain! He ensured we had an amazing time, and had a lime out by Mona’s Island. Our bachelorette trip would have not been complete without Ronald & the Whistling Wind.
Find the right listing for you and your crew, with options for boat types, group size, captained or self-charter, and lots more.
Found one you like? Send a rental inquiry with your preferred trip details, and you’ll receive an offer from your captain to book.
Coordinate a pick-up place and time, meet your boat captain, and get out onto the water!
August 01, 2023
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October 03, 2022
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December 11, 2019
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August 24, 2023
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April 10, 2020
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December 30, 2019
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