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All listings in Caribbean

Awesome sailboat rentals in the Caribbean.

4.7
(2,344 Reviews)

Page 3 of 18431 listings

Fountaine Pajot Great Sailing Catamaran for up to 25 people!
Sailing in Cartagena · 25 guests

Fountaine Pajot Great Sailing Catamaran for up to 25 people!

4.6
Superowner
$1,600/day
Exclusive Escape with Ocean Explorer Catamaran in Punta Cana
Powerboats in Uvero Alto · 30 guests

Exclusive Escape with Ocean Explorer Catamaran in Punta Cana

4.8
Superowner
Best of 2026
$16/hour
44 Luxury Catamaran BIG BEN
Sailing in Leeward Settlement · 18 guests

44 Luxury Catamaran BIG BEN

5.0
$875+/hour
Lagoon 38 Catamaran trip in St Martin with skipper, departure from Orient bay
Sailing in Saint Martin · 12 guests

Lagoon 38 Catamaran trip in St Martin with skipper, departure from Orient bay

4.9
Superowner
$1,155/day
Private Sail Aboard Classic 1969 Sloop in San Juan, Puerto Rico
Sailing in San Juan · 6 guests

Private Sail Aboard Classic 1969 Sloop in San Juan, Puerto Rico

4.9
Superowner
$198/hour
Punta Cana Booze Cruise Experience  Snorkeling • Sandbar • Music
Events in Punta Cana · 180 guests

Punta Cana Booze Cruise Experience Snorkeling • Sandbar • Music

4.0
Superowner
Best of 2026
$17/hour
⛵️ Catamaran Party Boat with Captain & Crew – Up to 42 Guests!
Sailing in Miami Beach · 42 guests

⛵️ Catamaran Party Boat with Captain & Crew – Up to 42 Guests!

4.8
Superowner
$700+/hour
🏝️Exciting Private Yacht: Affordable Charter with Crew🎉
Events in Punta Cana · 250 guests

🏝️Exciting Private Yacht: Affordable Charter with Crew🎉

3.0
Superowner
Best of 2026
$17/hour
⛵️ Catamaran 49-Person Party Boat Includes: 1-Captain, 1-Mate and 1-Bartender
Sailing in Miami Beach · 49 guests

⛵️ Catamaran 49-Person Party Boat Includes: 1-Captain, 1-Mate and 1-Bartender

5.0
Superowner
$700+/hour
Limited Availability
3.5hr Catamaran Experience Montego Bay
Sailing in Montego Bay · 30 guests

3.5hr Catamaran Experience Montego Bay

5.0
Superowner
$834/hour
Sail In Caribbean Paradise with Jeanneau Sun Odyssey 44
Sailing in Jolly Harbour · 6 guests

Sail In Caribbean Paradise with Jeanneau Sun Odyssey 44

4.9
$62+/hour
60ft AIcon Yacht – Perfect for Luxury Day Trips
Events in Miami · 13 guests

60ft AIcon Yacht – Perfect for Luxury Day Trips

4.8
$350/hour
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 From Pompano Beach, FL
Sailing in Pompano Beach · 12 guests

Sailing From Pompano Beach, FL

4.6
Superowner
$125+/hour
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
Curacao Private Romantic Sunset Tour 2p
Sailing in Santa Barbara Plantation · 2 guests

Curacao Private Romantic Sunset Tour 2p

5.0
$250/hour
Limited Availability
3hr Classic Yacht Experience Montego Bay
Powerboats in Montego Bay · 35 guests

3hr Classic Yacht Experience Montego Bay

5.0
Superowner
$933/hour
Let's go Sailing in Miami!
Sailing in Miami · 6 guests

Let's go Sailing in Miami!

5.0
$45+/hour
Janise Sailing Afternoon Charter - Fajardo, Puerto Rico 🇵🇷
Sailing in Fajardo · 6 guests

Janise Sailing Afternoon Charter - Fajardo, Puerto Rico 🇵🇷

4.9
$995/day
34ft Pacific Seacraft Sailboat for full day Trip in Santa Marta, Magdalena
Sailing in Santa Marta · 12 guests

34ft Pacific Seacraft Sailboat for full day Trip in Santa Marta, Magdalena

5.0
$100/hour
🏆🎉LUXURY YACHT RENTED BY OWNER- Best 2025- 2026 Awards TOTALLY PRIVATE 🎉
Events in Verón · 100 guests

🏆🎉LUXURY YACHT RENTED BY OWNER- Best 2025- 2026 Awards TOTALLY PRIVATE 🎉

4.8
Superowner
Best of 2026
$50/hour
Limited Availability
Private Tours~ Snorkeling at Palomino & Icacos Islands- Pursuit 28'
Tours in Fajardo · 6 guests

Private Tours~ Snorkeling at Palomino & Icacos Islands- Pursuit 28'

5.0
Superowner
Best of 2026
$675/day
Private Sailing Full Day Charter - Fajardo, Puerto Rico
Sailing in Fajardo · 6 guests

Private Sailing Full Day Charter - Fajardo, Puerto Rico

5.0
$1,995/day
Sea Ray Sundancer 38ft – Classic Luxury Cruise in Miami!
Events in Miami · 13 guests

Sea Ray Sundancer 38ft – Classic Luxury Cruise in Miami!

5.0
$100/hour

Sailing Reviews in Caribbean

  1. ML

    Myeves

    Private Tours~ Snorkeling at Palomino & Icacos Islands- Pursuit 28'

    i had the most amazing time. from all the gadgets they had like floaters, beach volleyball, and snorkels/flippers we were set up for success!!! he took such good care of us and even pointed out where to snorkel, WE GOT TO SEE TURTLES !!! food was delicious and service was great (at one point i had salt water in my eye and he helped wipe it!). truly an amazing group of gentleman that i hope i get to meet again!

  2. PC

    Paris

    Private Tours~ Snorkeling at Palomino & Icacos Islands- Pursuit 28'

    ⭐⭐⭐⭐⭐ We had an amazing experience and couldn’t have asked for a better day on the water! The captain took us to beautiful spots with crystal-clear water, and each stop was perfect for swimming and relaxing. The snorkeling was incredible, with plenty to see and a great selection of gear provided. The food was fresh and delicious, and the drinks kept coming all day. You can tell they truly care about making sure everyone has a fun, memorable experience. If you’re looking for a private boat trip in Puerto Rico, I highly recommend booking with them. Professional, friendly, and worth every penny. This was easily one of the highlights of our vacation, and we would absolutely book again!

  3. lb

    lauren

    Lagoon 38 Catamaran trip in St Martin with skipper, departure from Orient bay

    We had a wonderful day on this boat! The captain was great, took us to the best spots for snorkeling and lunch, and we loved leaving from Orient Bay so we didn’t have to sail as long in the rougher waters. Spectacular day all around and highly recommend

  4. Nelson

    Nelson

    Private Tours~ Snorkeling at Palomino & Icacos Islands- Pursuit 28'

    Jose and his crew were fantastic. The food was excellent, communication was great, timing was spot on, and the service throughout the entire experience was outstanding. Highly recommend!

  5. CB

    Charlene

    Exclusive Escape with Ocean Explorer Catamaran in Punta Cana

    Thank you for your prompt communication and competitive pricing! I very much appreciated your answers to all my questions before I booked for our group of 75 wedding guests. The slide was a highlight as the catamaran trip was a first for many guests. If I booked again, I would stay at the first stop for the entire time as the sandbar was really busy.

  6. JM

    Jordan

    Exclusive Escape with Ocean Explorer Catamaran in Punta Cana

    ⭐️⭐️⭐️⭐️⭐️ We had an amazing experience with this private hire boat during our family trip to the Dominican Republic! From the moment we boarded, everything was seamless—professional crew, beautiful boat, and top-tier service from start to finish. The crew was friendly, attentive to our young children , and made sure we were comfortable and having fun the entire time. They took us to stunning, secluded spots for swimming and snorkeling, and even arranged refreshments and music that made the vibe perfect for both the adults and the kids. The boat was clean, spacious, and well-equipped. It truly felt like a luxury experience. We created memories we’ll cherish forever, and I can’t recommend this enough if you’re looking for a relaxing and unforgettable way to explore the coast. Would absolutely book again! Once again thank you to the crew and leydis for such an amazing booking ⭐️⭐️⭐️⭐️⭐️