Cookies & Agreements

By continuing to use this website, you have read and agree to the Terms of Use and agree to the collection and use of your information by cookies and similar technologies, as set forth in our Privacy Policy.

Caribbean Boat Rentals & Yacht Charters - 2026

4.8
(25,223 Reviews)

Page 46 of 142 • 3,390 listings

Charter 42' Whistle Wind Motor Yacht in Port of Spain, Trinidad and Tobago
Events in Trinidad and Tobago · 20 guests

Charter 42' Whistle Wind Motor Yacht in Port of Spain, Trinidad and Tobago

5.0
$910/day
2026 VIP Birthday Celebration - Bachelor-bachelorette And More! Book Now!
Events in Bávaro · 100 guests

2026 VIP Birthday Celebration - Bachelor-bachelorette And More! Book Now!

New
Superowner
Best of 2026
$17/hour
31' Wellcraft. New, Fast Powerboat for Full Day in St. Thomas
Powerboats in St. Thomas · 12 guests

31' Wellcraft. New, Fast Powerboat for Full Day in St. Thomas

5.0
$1,450/day
62' Azimut “Priceless” | Luxury Miami Yacht Charter
Events in Miami Beach · 13 guests

62' Azimut “Priceless” | Luxury Miami Yacht Charter

5.0
$680+/hour
Visit Saona Island and Natural Pool renting our yacht from Punta Cana
Events in Punta Cana · 12 guests

Visit Saona Island and Natural Pool renting our yacht from Punta Cana

5.0
$2,120/day
Stunning 35ft Sea Ray Sundancer Yacht in Miami for 12 Guests
Events in Miami · 12 guests

Stunning 35ft Sea Ray Sundancer Yacht in Miami for 12 Guests

New
Superowner
Best of 2026
$125/hour
Double Decker 42' Aventura Private Catamaran
Powerboats in Nassau · 59 guests

Double Decker 42' Aventura Private Catamaran

5.0
$1,100/hour
37 Foot Intrepid Center Console for 12 People in St John, U.S. Virgin Islands
Powerboats in Cruz Bay · 12 guests

37 Foot Intrepid Center Console for 12 People in St John, U.S. Virgin Islands

5.0
$1,350/day
Set Sail Nassau on Our 53ft Leopard Power Cat
Powerboats in Nassau · 13 guests

Set Sail Nassau on Our 53ft Leopard Power Cat

New
Superowner
Best of 2026
$380/hour
Cobalt R5 Bowrider Boat Rental In George Town, Cayman Islands
Powerboats in George Town · 8 guests

Cobalt R5 Bowrider Boat Rental In George Town, Cayman Islands

5.0
$288+/hour
Beautiful Power Boat for Rent in Noord, Aruba
Powerboats in Noord · 12 guests

Beautiful Power Boat for Rent in Noord, Aruba

5.0
Superowner
$350/hour
Luxury Day Catamaran Charters ANTIGUA
Sailing in Saint John's · 65 guests

Luxury Day Catamaran Charters ANTIGUA

5.0
$1,000/hour
Key West Center Console: Your Perfect Day Boat Awaits!
Powerboats in Boynton Beach · 8 guests

Key West Center Console: Your Perfect Day Boat Awaits!

5.0
$84+/hour
St. Kitts Coastline Cruise & Beach
Tours in Basseterre · 45 guests

St. Kitts Coastline Cruise & Beach

5.0
$147/hour
24ft Hurricane Deck Boat for Amazing Day in SWFL
Powerboats in Naples · 6 guests

24ft Hurricane Deck Boat for Amazing Day in SWFL

5.0
$120+/hour
23ft Godfrey Marine "White Pearl" Charter in Naples. FL
Powerboats in Naples · 6 guests

23ft Godfrey Marine "White Pearl" Charter in Naples. FL

5.0
$300/hour
Luxury 60ft Prestige Yacht: Flybridge, Sunbed Lounge & VIP Experience in Miami
Events in Miami · 13 guests

Luxury 60ft Prestige Yacht: Flybridge, Sunbed Lounge & VIP Experience in Miami

New
Superowner
$400/hour
Sailing Cruise Saint John
Sailing in Cruz Bay · 6 guests

Sailing Cruise Saint John

5.0
$197/hour
Inflatable motorboat 7 meters 2 x 115 hp 12 persons
Powerboats in Saint Martin · 12 guests

Inflatable motorboat 7 meters 2 x 115 hp 12 persons

5.0
Superowner
$613/day
Discover the Island's, South Paradise aboard our Bayliner 2659 Rendezvous Boat!!
Powerboats in Salinas · 6 guests

Discover the Island's, South Paradise aboard our Bayliner 2659 Rendezvous Boat!!

5.0
$150/hour
Yacht Prestige 50 On La Romana Country House
Events in La Romana · 15 guests

Yacht Prestige 50 On La Romana Country House

New
$4,680/day
Nassau: Island Hopping, Snorkeling, Swimming Pigs Adventure and Private Tour
Powerboats in Nassau · 10 guests

Nassau: Island Hopping, Snorkeling, Swimming Pigs Adventure and Private Tour

5.0
$200/hour
Azimut 50 Motoryacht to Enjoy The Stunning Islands
Events in Fajardo · 12 guests

Azimut 50 Motoryacht to Enjoy The Stunning Islands

3.0
$350+/hour
Limited Availability
Explore Cartagena Aboard 42' Iconique B1 with Captain for 12 Guests
Events in Cartagena · 12 guests

Explore Cartagena Aboard 42' Iconique B1 with Captain for 12 Guests

5.0
Superowner
$200/hour

Caribbean Reviews

  1. Auston

    Auston

    Charter 42' Whistle Wind Motor Yacht in Port of Spain, Trinidad and Tobago

    From start to finish, our trip “down de islands” was absolutely amazing. Ronald is the perfect captain—professional, friendly, and full of local knowledge that made the whole experience even better. The boat was clean, comfortable, and well-equipped, and we always felt safe and well taken care of. Ronald took us to the best spots for swimming, liming, and taking in those breathtaking sunset views and a surprise visit from dolphins you can only get in beautiful Trinidad. His warm personality and easygoing vibe made the day feel like we were out with an old friend. If you’re looking for the perfect DDI experience whether it’s relaxation or adventure Ronald’s Charter is the one to book. Highly recommend and definitely planning to go again!

  2. JL

    Jill

    Charter 42' Whistle Wind Motor Yacht in Port of Spain, Trinidad and Tobago

    We had a wonderful time with Ronald. He was helpful, friendly and really made us feel comfortable. He saw we had a lot of food / snacks and got us a trolley and helped us load up the boat! He provided some cool history about going down the islands, and pointed out cool things along the way. We felt safe and he really made us feel like family! You can't go wrong with booking him for a wonderful day out on the seas.

  3. Alexandra

    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!!!

  4. Ma Estela

    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.

  5. MG

    Maria

    Charter 42' Whistle Wind Motor Yacht in Port of Spain, Trinidad and Tobago

    Beautiful boat, great captain - we had an amazing time on Ronald's boat. It was the most perfect way to relax after carnival with friends. 4 hours wasn't nearly enough :) P.S. Booking process was quick and easy. Ronal responded right away and maintained quick and clear communication from booking to the time we arrived at the Yacht Club and Ronald met us at the gate.

  6. ZP

    Zachary

    Charter 42' Whistle Wind Motor Yacht in Port of Spain, Trinidad and Tobago

    My family & I had a wonderful time with Capt. Ronnie and his wonderful vessel, Whistle Wind. He is extremely knowledgeable and a pleasure to be around. My two boys felt right at home on the WW and my 89-year old father was taken care of appropriately the entire time. Would gladly rec’d Capt. Ronnie to anyone looking for an afternoon on the ocean.