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All listings in Caribbean

Awesome sailboat rentals in the Caribbean.

4.7

(2,411 Reviews)

Page 11 of 20 • 460 listings

Events in Sosúa · 25 guests

Unforgettable Private Sunset Cruise in Punta Cana - Luxury VIP Boat Experience

New

$135/hour

Sailing in Bávaro · 60 guests

Private 6-Hour Sailing Catamaran Charter in Punta Cana – Esmeralda

New

$265+/hour

Instant Book

Sailing in Cartagena · 30 guests

Fountaine Pajot Saba 50 – Luxury Catamaran Charter Experience

New

Superowner

$425/hour

Sailing in Cartagena · 15 guests

Enjoy an exclusive experience aboard the Leopard 38' Catamaran

New

Superowner

$230/hour

Limited Availability

Sailing in Fort Lauderdale · 12 guests

57' Fountaine Pajot Sailing Catamaran - A Luxury Experience

5.0

$450/hour

Powerboats in Cartagena · 40 guests

Private 45ft Catamaran — Cartagena & Rosario Islands

New

$4,999/day

Sailing in Fort Lauderdale · 12 guests

50 Luxury Sailing Catamaran in Miami

5.0

$330/hour

Sailing in Montego Bay · 60 guests

Montego Bay Private Catamaran Cruise with Open Bar & Snorkeling

New

$4,049/day

Sailing in Cartagena · 14 guests

Charter the yacht of your dreams Jeanneau 54 Cruising Monohull in Cartagena

New

Superowner

$200/hour

Powerboats in Ocho Rios · 100 guests

Private Sunset Dinner Catamaran Ocho Rios – Jamaican Dinner, Open Bar & DJ

New

$3,590/day

Instant Book

Events in Dominican Republic · 70 guests

Bahia de las Aguilas- Private Catamaran Cruise

New

$750/hour

Sailing in Los Melones · 35 guests

Private 47ft Power Catamaran to Saona Island – Full-Day All-Inclusive Experience

New

$850/hour

Instant Book

Powerboats in The Bight Settlement · 10 guests

Turks & Caicos Private Sunrise 27' Sea Ray Boat Charter

New

$525/hour

Sailing in Cartagena · 20 guests

Lagoon 440 Sailing Catamaran Charter from Cartagena

New

$231+/hour

Sailing in Boynton Beach · 12 guests

Sail from Boynton Beach to Lake Boca

New

Superowner

$126+/hour

Sailing in Cartagena · 12 guests

Hit the water on Beneteau 50 Cruising Monohull in Cartagena, Colombia

New

Superowner

$150/hour

Sailing in Dominican Republic · 65 guests

Private Catamaran to Bahia de las Aguilas Cabo Rojo

New

$400/hour

Sailing in Cartagena · 10 guests

Have an amazing time in Cartagena, Colombia on Bavaria 51 Cruising Monohull

New

Superowner

$163/hour

Sailing in Les Abymes · 10 guests

Sailing Cruise Guadeloupe to Martinique on Beneteau Oceanis 440

New

$223/day

Sailing in Rodney Bay · 6 guests

Weekly Caribbean Sailing Cruise from Saint Lucia on 44ft Beneteau Yacht

New

$1,114/day

Sailing in St. Thomas · 6 guests

46' Monohull Sailing Private Charter in Charlotte Amalie

New

$200/hour

Sailing in Bávaro · 70 guests

Punta Cana Sunset Catamaran Cruise with BBQ, Champagne & Music

New

$500/hour

Instant Book

Tours in Miami Beach · 10 guests

Private Yacht Tour — Miami Skyline Sunset Cruise with Bottle of Champagne

New

Superowner

$159+/hour

Sailing in Miami · 12 guests

42' Luxury Catamaran Sailboat

New

$300/hour

Top Destinations Nearby

Sailing Reviews in Caribbean

Margaux

50 Luxury Sailing Catamaran in Miami
We had an absolutely amazing experience with this boat charter! From start to finish, everything was seamless, and it was easily one of the highlights of our trip. The boat was beautiful, clean, and exactly as advertised, and there was plenty of space for everyone to relax and enjoy the day. Our captain, Leo, was exceptional. He was professional, friendly, and incredibly accommodating. He made sure we were comfortable throughout the entire trip and did a great job showing us around and finding some beautiful spots to enjoy. He was also super knowledgeable about the area and made the whole experience feel effortless while still being a lot of fun. Leo really went above and beyond to make sure we had an unforgettable day. We had such a great time and would absolutely book with them again. Highly recommend requesting Leo as your captain — he was fantastic!
TL
Tanya

46' Monohull Sailing Private Charter in Charlotte Amalie
Captain Fancy and Lindsey were awesome!! We loved every minute of it. Pedro the pirate dog was so sweet. I would post pictures but not sure how. I don’t see an option.
SA
Sharon

50 Luxury Sailing Catamaran in Miami
Just book it! You will NOT regret it. I promise- it's an amazing experience! The crew (Leornardo and Alina) were awesome and very accommodating! Book with these two!
Blue

50 Luxury Sailing Catamaran in Miami
Leo and crew were fantastic, and my friends and I had a blast out on the water! Can't wait to do it again.
erkan

57' Fountaine Pajot Sailing Catamaran - A Luxury Experience
Crew , boat , owner … they were the best !