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All listings in Caribbean

Awesome sailboat rentals in the Caribbean.

4.7

(2,371 Reviews)

Page 10 of 19 • 433 listings

Sailing in Cartagena · 80 guests

Maxicat 65ft Private Party Catamaran in Cartagena

New

Superowner

$838/hour

Sailing in Miami · 12 guests

42' Luxury Catamaran Sailboat

New

$300/hour

Sailing in Barrio Las Yaguitas · 80 guests

Cruising Catamaran Rental in Puerto Plata, Puerto Plata

1.0

Superowner

Best of 2026

$183/hour

Powerboats in Sosúa · 70 guests

Puerto Plata Luxury Catamaran Charter with Snorkeling & Lunch

New

$242/hour

Instant Book

Sailing in Cartagena · 23 guests

An amazing charter experience - Lagoon 44 Cruising Catamaran in Cartagena

New

Superowner

$231/hour

Sailing in Bávaro · 200 guests

Punta Cana - FAMILY BOAT

New

$160/hour

Events in Bávaro · 12 guests

39ft Sea Ray Motor Yacht in Punta Cana, La Altagracia

New

$1,910/day

Powerboats in Ocho Rios · 100 guests

Dunn’s River Falls Private Catamaran Cruise – Ocho Rios

New

$654/hour

Events in Sosúa · 25 guests

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

New

$135/hour

Sailing in Montego Bay · 60 guests

Montego Bay Private Catamaran Cruise with Open Bar & Snorkeling

New

$1,176/hour

Sailing in Cartagena · 80 guests

Have an amazing time on Maxi Cat 65 Cruising Catamaran in Cartagena, Colombia

New

Superowner

$5,000/day

Sailing in Saint John's · 65 guests

Luxury Day Catamaran Charters ANTIGUA

5.0

$1,000/hour

Sailing in Cartagena · 14 guests

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

New

Superowner

$200/hour

Limited Availability

Sailing in Fort Lauderdale · 12 guests

57' Fountaine Pajot Sailing Catamaran - A Luxury Experience

5.0

$450/hour

Sailing in El Cortecito · 70 guests

Champagne Sunset Cruise – Private Catamaran (5:00 PM – 7:00 PM)

New

$644/hour

Instant Book

Powerboats in Ocho Rios · 100 guests

Ocho Rios Private Sunset Catamaran with Dinner & Open Bar

New

$817/hour

Sailing in Bávaro · 70 guests

Punta Cana Sunset Catamaran Cruise with BBQ, Champagne & Music

New

$500/hour

Instant Book

Events in Dominican Republic · 70 guests

Bahia de las Aguilas- Private Catamaran Cruise

New

$500/hour

Tours in Miami Beach · 10 guests

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

New

Superowner

$159+/hour

Sailing in Boynton Beach · 12 guests

Sail from Boynton Beach to Lake Boca

New

Superowner

$126+/hour

Sailing in Fajardo · 44 guests

47ft Private Custom Catamaran Charter in Fajardo, Puerto Rico

New

$800/hour

Sailing in Cartagena · 12 guests

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

New

Superowner

$150/hour

Sailing in Charlotte Amalie · 6 guests

Sailing catamaran in USVI

5.0

$1,300/day

Tours in Basseterre · 45 guests

Twin Island Paradise Snorkel Tour

New

$29/hour

Top Destinations Nearby

Sailing Reviews in Caribbean

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.
Shayna

Luxury Day Catamaran Charters ANTIGUA
We held our small wedding on one of Craig's boats and it was perfect! Fun and amazing crew, great food, awesome drinks, and all around an unforgettable experience. Would definitely book again next time we are on the island!
Kim

Luxury Day Catamaran Charters ANTIGUA
This private catamaran for my group of 27 was amazing! The tour guide was fun and engaging with my group. The private Island we visited was beautiful ! The food was great and better than we expected !
Justin

Luxury Day Catamaran Charters ANTIGUA
So much fun!! The booking process was easy and the crew was awesome!
Shayna

Luxury Day Catamaran Charters ANTIGUA
We always have a wonderful experience! We will be booking again!
KM
Kristin

Luxury Day Catamaran Charters ANTIGUA
Great communication, amazing captain and crew. Highly recommend