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All listings in Caribbean

Awesome sailboat rentals in the Caribbean.

4.8
(2,136 Reviews)

Page 5 of 17402 listings

Fort Lauderdale Bahamas Sailing Charters
Sailing in Fort Lauderdale · 6 guests

Fort Lauderdale Bahamas Sailing Charters

5.0
$130+/hour
Sunset Cruise in San Juan Puerto Rico
Sailing in San Juan · 6 guests

Sunset Cruise in San Juan Puerto Rico

5.0
Superowner
$353/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 2025
$50/hour
Sail Miami! Beautiful Beneteau 43 Cruising Monohull
Sailing in Miami · 10 guests

Sail Miami! Beautiful Beneteau 43 Cruising Monohull

5.0
$170/hour
Lagoon 400 18 People Cruising Catamaran In Cartagena, Colombia
Sailing in Cartagena · 18 guests

Lagoon 400 18 People Cruising Catamaran In Cartagena, Colombia

5.0
$1,600/day
Saint Kitts Private Boat Charter
Tours in Basseterre · 55 guests

Saint Kitts Private Boat Charter

5.0
$300/hour
44' Wellington Sailing Yacht In Antigua
Sailing in Jolly Harbour · 6 guests

44' Wellington Sailing Yacht In Antigua

5.0
$100/hour
Instant Book
Private Party Boat Available for your party in our Beautiful Beaches
Events in Bávaro · 30 guests

Private Party Boat Available for your party in our Beautiful Beaches

New
Superowner
$100/hour
Punta Cana - PRIVATE SMALL GROUP (CAT PAUSE)
Sailing in Bávaro · 15 guests

Punta Cana - PRIVATE SMALL GROUP (CAT PAUSE)

5.0
$250/hour
!!Best 2025 Winner !! Power Catamaran in La Romana, Dominican Republic
Events in La Romana · 100 guests

!!Best 2025 Winner !! Power Catamaran in La Romana, Dominican Republic

5.0
Superowner
Best of 2025
$60/hour
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 2025
$100/hour
The Best Boat For You And Your Friends NERO
Events in Miami · 13 guests

The Best Boat For You And Your Friends NERO

New
Superowner
$365+/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
Imagine Sailing Catamaran Charter in Simpson Bay, Sint Maarten
Sailing in Cole Bay · 12 guests

Imagine Sailing Catamaran Charter in Simpson Bay, Sint Maarten

5.0
$190/hour
60' Sailing Party Catamaran in Miami Florida ($1,300 PER HOUR)
Travel in Miami Beach · 49 guests

60' Sailing Party Catamaran in Miami Florida ($1,300 PER HOUR)

4.6
$1,300/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
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
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
🛥️🏝️ SAIL IN PUNTA CANA PRIVATE GROUPS 🛥️🏝️
Tours in Dominican Republic · 40 guests

🛥️🏝️ SAIL IN PUNTA CANA PRIVATE GROUPS 🛥️🏝️

New
Superowner
Best of 2025
$75/hour
Fountaine Pajot 40ft Catamaran! African Dream, Turks and Caicos
Sailing in Leeward Settlement · 10 guests

Fountaine Pajot 40ft Catamaran! African Dream, Turks and Caicos

5.0
$728+/hour
Best Day Ever! Private, All Inclusive & Custom Sailing, Snorkeling, Adventure!
Sailing in St. Thomas · 10 guests

Best Day Ever! Private, All Inclusive & Custom Sailing, Snorkeling, Adventure!

5.0
$225/hour
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
Rinker 260 Fiesta for Private family boat tour for your event!
Events in Punta Cana · 6 guests

Rinker 260 Fiesta for Private family boat tour for your event!

New
Best of 2025
$60/hour
Sail In Caribbean Paradise with Jeanneau Sun Odyssey 44
Sailing in Jolly Harbour · 6 guests

Sail In Caribbean Paradise with Jeanneau Sun Odyssey 44

4.8
$280/day

Sailing Reviews in Caribbean

  1. LE

    Lia

    Fort Lauderdale Bahamas Sailing Charters

    Truly incredible experience with Jose and Alex. Absolutely magical adventure and highly recommended to anyone looking for an unforgettable time. The food was also out of this world and so much attention to detail in every moment. We will absolutely be back and everyone needs to experience this.

  2. Sofia

    Sofia

    Fort Lauderdale Bahamas Sailing Charters

    Wow, this was an incredible experience for a very reasonable price. Jose and Alexandria’s hospitality and generosity is unmatched. I left the boat with two new friends, and I will definitely be keeping their information for future trips. We did a trip around Fort Lauderdale, and we were lucky enough to see some dolphins! We swam around in the beautiful and refreshing water and we had some incredible snacks, wellness drinks, and a meal at the end. All very healthy, and we left the boat feeling much better than we did when we got on. That’s the power of high quality, healthy food. Everything about this trip was amazing, but I must say the best part was their kindness. They took great care of me and my friends. Wonderful people and a very impressive boat!

  3. AH

    Andrew

    Fort Lauderdale Bahamas Sailing Charters

    I cannot overstate how wonderful our afternoon sail was with Jose and Luke. The weather was perfect, the boat in correct order, and each phase of the experience was conducted seamlessly. With that said, the calming center of the day - and by far the main reason we had such a special time -was Jose. Every once in a while, you meet a special person who has mastered their craft, acts as an enthusiastic and patient instructor, while making sure each person was comfortable and happy. For some, sailing can be intimidating, especially when the wind and waves act up. Jose was 'present' every moment to show us the joys of switching from power to wind, with confidence and professionalism. While we have charted powerboats and sailboats, this particular experience is not to be missed. He even prepared us healthy, vegan food once we returned to dock, showing us being in nature, enjoying the sea, and having yummy healthy food is all part of finding some momentary tranquility. Book this experience! I know we will again.

  4. William

    William

    Fort Lauderdale Bahamas Sailing Charters

    Awesome and experienced Captain, Jose, who was a pleasure to spend time with. Great communication, very flexible to accommodate my individual aims for the sailing experience. Exceedingly accommodating to spend time on a special request to focus of our time on navigating dockage. His coaching made a big difference for me! 5 stars all the way!

  5. PA

    Patricio

    Fort Lauderdale Bahamas Sailing Charters

    Amazing experience, much better than expected! We were not excited due to cloudy weather, rain, and lack of wind. Jose and Alex turned a grey day into the highest point of our vacation! The boat is in great shape, Jose has tremendous experience, both Jose and Alex are extremely nice, they took the time and effort to motivate and teach sailing to our kids, while ensuring a fun sailing experience for us (the adults). Jose and Alex are incredible hosts!

  6. BK

    Brian

    Sunset Cruise in San Juan Puerto Rico

    Sailing with Jimbo was the highlight of our trip to San Juan! Can’t say enough about the whole experience. Jimbo gave great historical insights, was an engaging storyteller and most importantly was a great Captain that made the sail both exciting and safe. 10/10 would book again.