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All listings in Caribbean

Awesome sailboat rentals in the Caribbean.

4.8
(2,122 Reviews)

Page 6 of 17394 listings

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
Luxury Day Catamaran Charters ANTIGUA
Sailing in Saint John's · 65 guests

Luxury Day Catamaran Charters ANTIGUA

5.0
$1,000/hour
From Rodney Bay daily sailing cruise. 2-4 days from Saint Lucia to Martinique
Sailing in Gros Islet · 6 guests

From Rodney Bay daily sailing cruise. 2-4 days from Saint Lucia to Martinique

5.0
$1,081/day
Punta Cana - PRIVATE BOAT MAX BBQ
Sailing in Bávaro · 40 guests

Punta Cana - PRIVATE BOAT MAX BBQ

New
$575/hour
Catamaran Party Boat Includes: 1-Captain, 1-Mate and 1-Bartender
Sailing in Miami · 42 guests

Catamaran Party Boat Includes: 1-Captain, 1-Mate and 1-Bartender

1.0
Superowner
Best of 2025
$800/hour
Cruising Monohull Charter in Samaná, Dominican Republic
Sailing in Samana · 10 guests

Cruising Monohull Charter in Samaná, Dominican Republic

5.0
$1,586/day
Sailing Cruise Saint John
Sailing in Cruz Bay · 6 guests

Sailing Cruise Saint John

5.0
$197/hour
Private Yacht Tour — Miami Skyline Sunset Cruise with Bottle of Champagne
Tours in Miami Beach · 10 guests

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

New
Superowner
$159+/hour
Charter Lagoon 40 Sailing Catamaran Yacht In Cartagena, Colombia
Sailing in Cartagena · 15 guests

Charter Lagoon 40 Sailing Catamaran Yacht In Cartagena, Colombia

New
$250+/hour
SPRING BREAK TIME🛥🔥 VIP Luxury Catamaran Party Sailing-Swimming in Punta Cana
Events in Bávaro · 150 guests

SPRING BREAK TIME🛥🔥 VIP Luxury Catamaran Party Sailing-Swimming in Punta Cana

3.8
$167/hour
Private Sailing Full Day Charter - Fajardo, Puerto Rico
Sailing in Fajardo · 6 guests

Private Sailing Full Day Charter - Fajardo, Puerto Rico

New
$2,395/day
Luxury Sailing Catamaran Charter in Fajardo, Puerto Rico
Sailing in Ceiba · 19 guests

Luxury Sailing Catamaran Charter in Fajardo, Puerto Rico

5.0
$450/hour
Catamaran Lose 50 Country House La Romana
Sailing in La Romana · 20 guests

Catamaran Lose 50 Country House La Romana

New
$2,088/day
The Best Day Sail in St. Maarten
Sailing in Simpson Bay · 30 guests

The Best Day Sail in St. Maarten

5.0
$129/day
Enjoy Day Trips or Grenadines Cruises Onboard Our Luxury Catamaran
Sailing in Lance aux Epines · 6 guests

Enjoy Day Trips or Grenadines Cruises Onboard Our Luxury Catamaran

5.0
$800/day
Private Group Sail and Snorkel Montego Bay
Sailing in Montego Bay · 30 guests

Private Group Sail and Snorkel Montego Bay

5.0
$940/hour
Full Day 50' Private Sailing Catamaran. Luxury, Beach/Snorkel. Departs Red Hook
Sailing in St. Thomas · 12 guests

Full Day 50' Private Sailing Catamaran. Luxury, Beach/Snorkel. Departs Red Hook

5.0
$2,395/day
50ft Catamaran sail experience in Aruba. OPEN BAR AND BBQ included!!
Sailing in Oranjestad-West · 40 guests

50ft Catamaran sail experience in Aruba. OPEN BAR AND BBQ included!!

4.0
$1,120/hour
Private Sail tour to Les Saintes with Skipper Sailing teacher
Sailing in Saint Charles · 9 guests

Private Sail tour to Les Saintes with Skipper Sailing teacher

5.0
$1,409/day
28 GUESTS - OCEAN VOYAGER 53 CRUISING CATAMARAN
Events in The Valley · 28 guests

28 GUESTS - OCEAN VOYAGER 53 CRUISING CATAMARAN

New
$705/hour
30 foot Jupiter Center Console Rental in Fort Lauderdale, Florida
Powerboats in Deerfield Beach · 10 guests

30 foot Jupiter Center Console Rental in Fort Lauderdale, Florida

5.0
$200/hour
Mambo 40ft Sail Catamaran
Sailing in Simpson Bay · 20 guests

Mambo 40ft Sail Catamaran

5.0
$1,500/day
MAXIMA Powerboat 38ft in Cartagena de Indias
Powerboats in Cartagena · 20 guests

MAXIMA Powerboat 38ft in Cartagena de Indias

4.0
$830/day
2 Hour Sunset River Cruise for up to 6 people in Fort Lauderdale
Sailing in Fort Lauderdale · 6 guests

2 Hour Sunset River Cruise for up to 6 people in Fort Lauderdale

5.0
$150/hour

Sailing Reviews in Caribbean

  1. FS

    Felicia

    Sail In Caribbean Paradise with Jeanneau Sun Odyssey 44

    Eduardo and his captain were amazing. Super attentive especially with my older mom who was super nervous about sailing and swimming, while accommodating my energetic kids. They’re amazing, even taught us how to sail, it was super relaxing and something I’ll never forget. Definitely a must do when you’re in Antigua. I reached out to multiple boat owners and this is by far exceed expectations!!

  2. Peter

    Peter

    Sail In Caribbean Paradise with Jeanneau Sun Odyssey 44

    Thank you so much for this experience. We couldn’t have asked for a better time and Disco and Anu were both incredible. Nothing was too much for them and they were very knowledgeable and made the experience even more special. The recommendation from Disco to take us to Pinching Bay for our proposal was perfect. Thank you so much. God bless and long life Disco and Anu.

  3. MM

    Mike

    Sail In Caribbean Paradise with Jeanneau Sun Odyssey 44

    Hi Eduardo, We just finished up and have to tell you. We had a great time! Karis(Concord) made the trip unforgettable. We enjoyed the boat but without him it would not have been the same. He is truly a great person and I can say his praises enough. Took us all around (literally 360) Antigua!

  4. BB

    Benjamin

    Sail In Caribbean Paradise with Jeanneau Sun Odyssey 44

    We had a great day sailing on Voilactus! Super easy to find and park, and then the day sailing was excellent. We went to English Harbor and back, with time for swimming and lunch. Pure sailing. Totally recommend! You will have a great day if you are looking for a real sail!

  5. KM

    Kavan

    Luxury Day Catamaran Charters ANTIGUA

    So it’s my brother in law’s 50th birthday and we went to Antigua. Never been, but we needed to rent a boat that holds at least 20 people for about 5 hours of drinking partying and snorkeling around the coast of Antigua. I was nervous because I didn’t want to get scammed however, I took a chance and Craig was very responsive, gave a lot of insights on what to do and even checked in from time to time prior to our arrival on the island. We got picked up right at our hotel beach, one time and was greeted with some rum punch. The crew was friendly, fun, funny, and answered all our questions about the island. They were very flexible with what we wanted to do and the time that we needed to spend. All and all it was a great trip and I would recommend them to anyone. So if you are reading this don’t miss out on a great adventure.

  6. JW

    Jocelyn

    From Rodney Bay daily sailing cruise. 2-4 days from Saint Lucia to Martinique

    Alessandro was the best! He was so patient with my inquiries and answered my (many) questions. He was incredibly accommodating and communicative throughout the entire process and made me feel much more comfortable about booking a boating excursion in a foreign country! Highly recommend!