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All listings in Caribbean

Awesome sailboat rentals in the Caribbean.

4.7
(2,255 Reviews)

Page 6 of 18416 listings

Beautiful 57' Lagoon Sailing Catamaran
Sailing in Road Town · 12 guests

Beautiful 57' Lagoon Sailing Catamaran

5.0
$900/hour
🥂EXCLUSIVE ISLAND CRUISE ENTERTAINMENT BAR MUSIC DANCE PARTY CAPTAIN CHARTER 🏝
Events in Uvero Alto · 150 guests

🥂EXCLUSIVE ISLAND CRUISE ENTERTAINMENT BAR MUSIC DANCE PARTY CAPTAIN CHARTER 🏝

New
Superowner
Best of 2026
$17/hour
Full Day. Reserve a Luxury 47' Leopard Catamaran in St. Thomas, USVI
Sailing in Charlotte Amalie · 12 guests

Full Day. Reserve a Luxury 47' Leopard Catamaran in St. Thomas, USVI

5.0
$293/hour
Beautiful 36' Sea Ray Motor Yacht up to 12 guests and floating mat in Miami!!
Powerboats in Miami · 10 guests

Beautiful 36' Sea Ray Motor Yacht up to 12 guests and floating mat in Miami!!

4.3
$100+/hour
60' Sailing Party Catamaran in Miami Florida
Sailing in Miami Beach · 49 guests

60' Sailing Party Catamaran in Miami Florida

4.6
$1,300/hour
Limited Availability
Premium 47ft Exclusive Yacht Charter Rental Aruba
Events in Oranjestad-East · 10 guests

Premium 47ft Exclusive Yacht Charter Rental Aruba

5.0
$499/hour
Half Day Luxury Trips Aboard Our 47’ Sailing Yacht Catamaran
Sailing in Charlotte Amalie · 12 guests

Half Day Luxury Trips Aboard Our 47’ Sailing Yacht Catamaran

4.6
$365/hour
Luxury Catamaran Lagoon ' Capacity up to 18
Powerboats in Cartagena · 18 guests

Luxury Catamaran Lagoon ' Capacity up to 18

5.0
Superowner
$180/hour
The Best Day Sail in St. Maarten
Caribbean · 30 guests

The Best Day Sail in St. Maarten

5.0
$129/day
Sailing and motor Catamaran for Cruising and Celebrations🎉Best 2025 Awards 🎉
Sailing in Uvero Alto · 30 guests

Sailing and motor Catamaran for Cruising and Celebrations🎉Best 2025 Awards 🎉

3.5
Superowner
Best of 2026
$100/hour
🏆BEST 2025🏆Family Party Boat with Slide for from 1 to 100 people in Punta Cana
Tours in Punta Cana · 100 guests

🏆BEST 2025🏆Family Party Boat with Slide for from 1 to 100 people in Punta Cana

3.7
Superowner
Best of 2026
$50/hour
2025 VIP Birthday Celebration - Bachelor-bachelorette And More! Book Now!
Events in Bávaro · 100 guests

2025 VIP Birthday Celebration - Bachelor-bachelorette And More! Book Now!

New
Superowner
Best of 2026
$17/hour
Exclusive Private Yacht Snorkeling, Natural Sea Pool, Wild Beach, Book Now!
Events in Cabarete · 100 guests

Exclusive Private Yacht Snorkeling, Natural Sea Pool, Wild Beach, Book Now!

New
Superowner
Best of 2026
$17/hour
Awesome and Spacious Sea Ray 55’ 2009 Motor Yacht Rental in Fajardo, Puerto Rico
Events in Fajardo · 12 guests

Awesome and Spacious Sea Ray 55’ 2009 Motor Yacht Rental in Fajardo, Puerto Rico

5.0
$800/hour
Ultimate Day Sailing Charter Onboard 40' Baba Sailboat in St. Thomas
Sailing in St. Thomas · 6 guests

Ultimate Day Sailing Charter Onboard 40' Baba Sailboat in St. Thomas

5.0
$220/hour
Luxury Sailing Catamaran Charter in Fajardo, Puerto Rico
Sailing in Fajardo · 19 guests

Luxury Sailing Catamaran Charter in Fajardo, Puerto Rico

5.0
$450/hour
All-inclusive Luxury Private Charter - Power Cat - St Martin/Anguilla/St Barths
Caribbean · 12 guests

All-inclusive Luxury Private Charter - Power Cat - St Martin/Anguilla/St Barths

5.0
$2,269+/day
Cruising Monohull Charter in Samaná, Dominican Republic
Sailing in Samana · 10 guests

Cruising Monohull Charter in Samaná, Dominican Republic

4.0
$1,586/day
Sailing Charters On 37' Hunter Legend Cruising Monohull In Virgin Islands
Sailing in Charlotte Amalie West · 6 guests

Sailing Charters On 37' Hunter Legend Cruising Monohull In Virgin Islands

5.0
$210/hour
Be Happy 40ft - Private Catamaran Charter - Discover the beautiful St Maarten
Caribbean · 12 guests

Be Happy 40ft - Private Catamaran Charter - Discover the beautiful St Maarten

5.0
$1,850/day
All Inclusive 67' Fountaine Pajot Catamaran for Day and Overnight Charter
Sailing in Nassau · 24 guests

All Inclusive 67' Fountaine Pajot Catamaran for Day and Overnight Charter

5.0
$960/hour
Power in Las Galeras
Sailing in Las Galeras · 10 guests

Power in Las Galeras

New
$1,580/day
Sailing Cruise Saint John
Sailing in Cruz Bay · 6 guests

Sailing Cruise Saint John

5.0
$197/hour
Curacao Private Romantic Sunset Tour 2p
Sailing in Jan Thiel · 2 guests

Curacao Private Romantic Sunset Tour 2p

5.0
$250/hour

Sailing Reviews in Caribbean

  1. Elen

    Elen

    Premium 47ft Exclusive Yacht Charter Rental Aruba

    We had an incredible time on this yacht charter! The boat was beautiful, spacious, and impeccably maintained. Everything was organized perfectly, making for a relaxing and enjoyable experience from start to finish. The food was absolutely delicious, with great options and excellent quality. Combined with the stunning views, wonderful atmosphere, and fantastic service, it made for a truly memorable day on the water. If you're looking for a fun and luxurious experience, this is it. We made amazing memories and can't recommend it enough. We can't wait to book again!

  2. SH

    Sheri

    All Inclusive 67' Fountaine Pajot Catamaran for Day and Overnight Charter

    This boat is beautiful! The crew was attentive to our wants and needs! The food was fabulous! Would recommend 10 out of 10 !

  3. AF

    Angela

    The Best Day Sail in St. Maarten

    Diane & the crew was top notch!! We had a group of 18 & from start to finish everything was perfect!! I would definitely book with her again.

  4. VK

    Vai

    Full Day. Reserve a Luxury 47' Leopard Catamaran in St. Thomas, USVI

    Captain AnneMarie and Osay were amazing. They made our day absolutely amazing from couple great snorkeling areas, a ship wreck to water island for a great lunch, snorkeling, paddle boarding etc. They both kept it fun and Osay was always there to help, assist or just give you great conversation with a smile on his face. Must experience in St Thomas. Would recommend doing a full day as well.

  5. WB

    Wendy

    Full Day. Reserve a Luxury 47' Leopard Catamaran in St. Thomas, USVI

    We rented from Scott's company for June 9, 2021. He was very attentive to responding to questions about the rental. The boat was exacting what is advertised....fantastic! We had Captain Splash and O'say as a crew fro the day. They were fantastic. They were prompt and onetime. When we first meet they asked if there were any special food or beverages we would like. We asked if there was champagne on board...he said no and said he would get some. We offered to pay for it but they would not let us pay for it. Five of the quests were in their 70's and my husband moves a bit slow...they were very accommodating to him to get on, move around the boat and disembark the boat. That made my husbands trip be fabulous. We had 7 people in our group of which 3 remained on the back by captain splash while 4 of us spent most of the time on the front. Captain splash remained in the back talking and entertaining and O'say took care of use on the front making sure we had drinks, reminding us to reapply suntan lotion and telling us about all the islands we went around. Both very delightful and knowledgeable about the boat, islands and making our trip fabulous. They got us lunch at a fun shack on honeymoon island...Best fish tacos & wraps I ever had! The only regret is that we didn't rent the boat more than 1 day. DO NOT HESITATE TO RENT! Wendy Basford

  6. SN

    Shelby

    Full Day. Reserve a Luxury 47' Leopard Catamaran in St. Thomas, USVI

    10 starts!! (this is going to be a long one but an informative one) Wow is all you will say after you’v booked with the beat charter company on USVI! I don’t ever want to try any other company because theres no competition. This was the best experience ever! I cant wait to book again. Everyone and everything was nothing but amazing! I was speechless. First of all I took a beautiful sailing yacht called C'est La Vie with Seas the Day Charters(Scott and Hope). It was perfect for my birthday which hosted a party of 4. Very affordable, clean, spacious and just more than what I could’ve imagine. Our mate Alyssa and captain Pogan were absolutely wonderful! I don’t recall a time not seeing either one of them smiling. They were friendly and definitely helpful my party and I didn’t have to lift a finger. Captain Pogan was a smooth driver and knows his way around the waves. I booked the half day charter 9am-1pm and we didn’t want to leave! Captain Pogan took us to St. John from St. Thomas to a beautiful beach called Honeymoon beach (you also have the option of Trunk bay) where Alyssa carried us in a power boat to shore. We spent some time there and then she came back to get us. I felt very special on my day thank you so much! My booking included snacks like chips, peanuts, granola bars, cheeze its, unlimited rum punch, bottled water and sodas provided by the charter company. They also offer options for you to upgrade your charter by purchasing food, fruit, cakes, bottles of wine,champagne and anything else you may like to include on your day. I took advantage of this option by ordering a sandwich and fruit platers for my party. The young lady Hope who I’ve had conversations with about planning my charter experience is a real pleasure. Hope is super nice and sweet. I didn’t have any issues when it came to communicating with her via email or by phone. Whatever you want or need she will make it happen for you. I can’t say thank you enough!