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All listings in Caribbean

Awesome sailboat rentals in the Caribbean.

4.8
(2,289 Reviews)

Page 7 of 19441 listings

Private Luxury Bali 4.0 Catamaran with 3 Cabin from Old San Juan
Sailing in San Juan · 12 guests

Private Luxury Bali 4.0 Catamaran with 3 Cabin from Old San Juan

5.0
$575/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
Curacao Private Romantic Sunset Tour 2p
Sailing in Santa Barbara Plantation · 2 guests

Curacao Private Romantic Sunset Tour 2p

5.0
$250/hour
Cruising Monohull Charter in Samaná, Dominican Republic
Sailing in Samana · 10 guests

Cruising Monohull Charter in Samaná, Dominican Republic

4.0
$1,586/day
Sailing Cruise Saint John
Sailing in Cruz Bay · 6 guests

Sailing Cruise Saint John

5.0
$197/hour
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
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
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
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
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 Day Catamaran Charters ANTIGUA
Sailing in Saint John's · 65 guests

Luxury Day Catamaran Charters ANTIGUA

5.0
$1,000/hour
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
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
Passport 40 Sailboat in Key West - Comfortable Sailing for Up to 6 Guests
Sailing in Key West · 6 guests

Passport 40 Sailboat in Key West - Comfortable Sailing for Up to 6 Guests

New
$150/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
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
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
$745+/night
Aicon 67 Fly  – Elite Luxury Yacht Experience
Events in Miami · 13 guests

Aicon 67 Fly – Elite Luxury Yacht Experience

New
$350/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
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
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
Limited Availability
sunbathe and relax on our island in the middle of the ocean
Events in Punta Cana · 100 guests

sunbathe and relax on our island in the middle of the ocean

3.7
Superowner
Best of 2026
$50/hour
🥂EXCLUSIVE ISLAND CRUISE ENTERTAINMENT BAR MUSIC DANCE PARTY CAPTAIN CHARTER 🏝
Events in Bávaro · 100 guests

🥂EXCLUSIVE ISLAND CRUISE ENTERTAINMENT BAR MUSIC DANCE PARTY CAPTAIN CHARTER 🏝

New
Superowner
Best of 2026
$15/hour
3-Hours Puerto Plata Private Catamaran Cruise with BBQ Drinks and Snorkel
Powerboats in Sosúa · 15 guests

3-Hours Puerto Plata Private Catamaran Cruise with BBQ Drinks and Snorkel

New
$332/hour

Sailing Reviews in Caribbean

  1. AG

    Ashley

    Private Luxury Bali 4.0 Catamaran with 3 Cabin from Old San Juan

    The boat was immaculate and in pristine condition. The captain and crew were so professional and made our trip extra special. The boat was fully stocked with everything we needed. It was the perfect size for our group of 8 adults and was the highlight of our trip!

  2. LM

    Lauren

    Private Luxury Bali 4.0 Catamaran with 3 Cabin from Old San Juan

    This was a total highlight of our trip!!! The communication leading up to the charter was awesome and very prompt- all of my questions were answered. The captain (Krista!!) and crew were just amazing- truly had the most wonderful day. The boat is so comfortable, well stocked, and beautiful! They were super chill and worked with us on what we wanted to do and see. 10/10 would recommend and we will be back next time we come to PR!!!

  3. 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!!!!!

  4. 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!

  5. 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!

  6. 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.