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All listings in Caribbean

Awesome sailboat rentals in the Caribbean.

4.8
(2,279 Reviews)

Page 7 of 19433 listings

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
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
Power in Las Galeras
Sailing in Las Galeras · 10 guests

Power in Las Galeras

New
$1,580/day
Curacao Private Romantic Sunset Tour 2p
Sailing in Jan Thiel · 2 guests

Curacao Private Romantic Sunset Tour 2p

5.0
$250/hour
Isla Saona Private Yacht – Luxury Full-Day Tour
Powerboats in Bávaro · 20 guests

Isla Saona Private Yacht – Luxury Full-Day Tour

1.0
$1,820/day
Sailing Cruise Saint John
Sailing in Cruz Bay · 6 guests

Sailing Cruise Saint John

5.0
$197/hour
S/Y Timshel Day and Term Charters, Grenada and Grenadines
Sailing in Saint George's · 6 guests

S/Y Timshel Day and Term Charters, Grenada and Grenadines

5.0
$660/day
Great Catamaran for Cholon, Barú, sunset cruise, lunch or dinner on board...
Sailing in Cartagena · 45 guests

Great Catamaran for Cholon, Barú, sunset cruise, lunch or dinner on board...

4.9
Superowner
$1,000/day
LUXURY PARTY YACHT IN BAVARO PERFECT FOR ANY OCCASION 😎
Events in Bávaro · 80 guests

LUXURY PARTY YACHT IN BAVARO PERFECT FOR ANY OCCASION 😎

New
Superowner
Best of 2026
$16/hour
45' Lagoon Sailing Catamaran in St. Thomas, U.S. Virgin Islands
Sailing in St. Thomas · 12 guests

45' Lagoon Sailing Catamaran in St. Thomas, U.S. Virgin Islands

5.0
$2,000/day
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
Luxury Private Catamaran Charter – All-Inclusive from St. Maarten
Caribbean · 16 guests

Luxury Private Catamaran Charter – All-Inclusive from St. Maarten

5.0
$2,095/day
Luxury Day Catamaran Charters ANTIGUA
Sailing in Saint John's · 65 guests

Luxury Day Catamaran Charters ANTIGUA

5.0
$1,000/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
Imagine Sailing Catamaran Charter in Simpson Bay, Sint Maarten
Caribbean · 12 guests

Imagine Sailing Catamaran Charter in Simpson Bay, Sint Maarten

5.0
$1,500/day
All inclusive sailing charters, half day full day fishing week long sunset sail
Sailing in Charlotte Amalie · 12 guests

All inclusive sailing charters, half day full day fishing week long sunset sail

5.0
$250/hour
Instant Book
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
Punta Cana 60' Private Luxury Power Catamaran to Catalina Island
Powerboats in Punta Cana · 65 guests

Punta Cana 60' Private Luxury Power Catamaran to Catalina Island

New
$471/hour
Lagoon 42' Private Sailing Adventure in Florida with Captain Eric
Sailing in Deerfield Beach · 8 guests

Lagoon 42' Private Sailing Adventure in Florida with Captain Eric

5.0
$300/hour
COME AND ENJOY THE C'YA WITH US AND FAMILY
Events in Miami · 13 guests

COME AND ENJOY THE C'YA WITH US AND FAMILY

New
Superowner
$365+/hour
Catamaran Timaiao V, Crew included.  Saint Vincent and the Grenadines
Sailing in St. Andrew · 6 guests

Catamaran Timaiao V, Crew included. Saint Vincent and the Grenadines

5.0
$742+/night
Aicon 67 Fly  – Elite Luxury Yacht Experience
Events in Miami · 13 guests

Aicon 67 Fly – Elite Luxury Yacht Experience

New
$350/hour
40 ft Jeanneau Sloop Charter in Fort Lauderdale
Sailing in Fort Lauderdale · 6 guests

40 ft Jeanneau Sloop Charter in Fort Lauderdale

5.0
$109+/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

Sailing Reviews in Caribbean

  1. Caitlin

    Caitlin

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

    This was one of the best days of our lives! Christina and Jon were beyond accommodating. The drinks, the FOOD (get the lobster and mahi), the music, the snorkeling (saw so many beautiful fish and sea turtles!!) and the conversation were so enjoyable. These people know the islands so well and teach you a lot on top of giving you one of the best experiences of your life! Could not recommend it enough!!!!!

  2. KR

    Kelsey

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

    Jon and his team delivered the best experience of our St. John’s vacation. This is an island best seen by boat. Our kids are young (2,5,7). He customized an itinerary, snacks etc to the group. We went to one beautiful beach with turtles and a great snorkeling spot with fish. As our kids say, three thumbs up!

  3. LK

    Liz

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

    Jon and Christina were absolutely amazing! They made the experience so much fun and were very accommodating to everything we wanted to do, whether snorkeling, bringing us into to hang on the beach or whatever we wanted to experience. They also served the best food and drinks, it was the best part of our trip!

  4. ML

    Michael

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

    We have been on multiple day trips around the water during our stay on St. John. Our trip with Jon and Christina was by far the best experience. They actually asked us for input and what we would like to see and do. The lunch they served us was the best meal we have had here on St. John. Not only was it the best experience, it was also the best value. I highly recommend this duo for a great afternoon of sailing and snorkeling. We will be back.

  5. Cherry

    Cherry

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

    The crew are knowledgeable about the islands, serve the best mango dip appetizer, and delicious pork and mahi mahi meals. Their snorkeling equpment is like new and works great. They give you masks and fins plus noodles for those who need assistance. Great value for money.

  6. da

    david

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

    Terrific experience. Great sailing. Lots of good snorkeling. Saw turtles, rays, tons of fish and a sleeping baby shark. Food and drinks were terrific. John and Christina could not have been more generous. Did a private charter just with family which I highly recommend. For folks that are more interested in the experience than glitz, this is a terrific team.