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All listings in Caribbean

Awesome sailboat rentals in the Caribbean.

4.8
(1,991 Reviews)

Page 2 of 16379 listings

2.5hr Catamaran Experience Montego Bay
Events in Montego Bay · 30 guests

2.5hr Catamaran Experience Montego Bay

5.0
Superowner
Best of 2025
$995/hour
34ft Pacific Seacraft Sailboat for full day Trip in Santa Marta, Magdalena
Sailing in Comuna 2 · 12 guests

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

5.0
$100/hour
Instant Book
Cartagena Sunset & Bay Tour on a Large 38 feet Luxury Boat (Private Tour)
Powerboats in Cartagena · 16 guests

Cartagena Sunset & Bay Tour on a Large 38 feet Luxury Boat (Private Tour)

5.0
$129+/hour
Luxury Catamaran located in Downtown Miami
Sailing in Miami · 12 guests

Luxury Catamaran located in Downtown Miami

5.0
$219+/hour
Private Luxury Sailing Experience out of Old San Juan
Sailing in San Juan · 12 guests

Private Luxury Sailing Experience out of Old San Juan

5.0
$725/hour
Charter 45ft Cruising Catamaran In Christchurch, Barbados
Sailing in Welches · 26 guests

Charter 45ft Cruising Catamaran In Christchurch, Barbados

5.0
$250/hour
Exclusive Private boat rental to any occasion in punta cana🥳
Events in El Cortecito · 30 guests

Exclusive Private boat rental to any occasion in punta cana🥳

New
Superowner
$97/hour
44ft Sailing Catamaran Charter in Bridgetown, Saint Michael
Sailing in Henrys · 20 guests

44ft Sailing Catamaran Charter in Bridgetown, Saint Michael

5.0
$207/hour
Catamaran Party Boat up to 49 people. Includes: 1-Captain, 2-Mates
Sailing in Miami · 49 guests

Catamaran Party Boat up to 49 people. Includes: 1-Captain, 2-Mates

5.0
Superowner
Best of 2025
$800/hour
All-Inclusive Luxury Sailing Catamaran Charter from Paradise Island
Sailing in Nassau · 12 guests

All-Inclusive Luxury Sailing Catamaran Charter from Paradise Island

5.0
$600/hour
Instant Book
Beneteau Oceanis 473 Luxury Sailing Charter in Grand Cayman, Cayman Islands
Sailing in West Bay · 15 guests

Beneteau Oceanis 473 Luxury Sailing Charter in Grand Cayman, Cayman Islands

5.0
$350/hour
3.5hr Catamaran Experience Montego Bay
Sailing in Montego Bay · 30 guests

3.5hr Catamaran Experience Montego Bay

5.0
Superowner
Best of 2025
$834/hour
🤩VIP EXPERIENCE🛥🍾ALL INCLUDED CATAMARAN 4 Bachelorette-Birthday In Punta Cana
Powerboats in Punta Cana · 80 guests

🤩VIP EXPERIENCE🛥🍾ALL INCLUDED CATAMARAN 4 Bachelorette-Birthday In Punta Cana

4.5
$85/hour
Sailing Charter On 39' Catalina Sailboat In Fort Lauderdale, Florida
Tours in Fort Lauderdale · 6 guests

Sailing Charter On 39' Catalina Sailboat In Fort Lauderdale, Florida

5.0
Superowner
$119+/hour
44' Cruising Monohull Charter in Kralendijk, Caribbean Netherlands
Sailing in Kralendijk · 14 guests

44' Cruising Monohull Charter in Kralendijk, Caribbean Netherlands

5.0
$283/hour
3hr Classic Yacht Experience Montego Bay
Powerboats in Montego Bay · 25 guests

3hr Classic Yacht Experience Montego Bay

5.0
Superowner
Best of 2025
$933/hour
FULLY CUSTOMIZABLE Luxury Catamaran Charter
Sailing in Nassau · 12 guests

FULLY CUSTOMIZABLE Luxury Catamaran Charter

5.0
$665/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
Best of 2025
$800/hour
Catamaran Party Boat (49 Max) Includes: 1-Captain, 1-Mate and 1-Bartender
Sailing in Miami Beach · 49 guests

Catamaran Party Boat (49 Max) Includes: 1-Captain, 1-Mate and 1-Bartender

5.0
Superowner
Best of 2025
$800/hour
Janise Sailing Afternoon Charter - Fajardo, Puerto Rico 🇵🇷
Sailing in Fajardo · 6 guests

Janise Sailing Afternoon Charter - Fajardo, Puerto Rico 🇵🇷

4.9
$995/day
Instant Book
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
Instant Book
ALL FEES INCLUDED! Endeavor 43 Sailboat Charter out of Miami.
Sailing in Miami · 4 guests

ALL FEES INCLUDED! Endeavor 43 Sailboat Charter out of Miami.

5.0
Superowner
$75+/hour
Private Tours & Snorkeling at Flamenco Beach Culebra or Culebrita Island
Tours in Fajardo · 6 guests

Private Tours & Snorkeling at Flamenco Beach Culebra or Culebrita Island

5.0
Superowner
Best of 2025
$1,500/day
Board our Azimut Flybridge 42' for an unforgettable experience!
Events in Miami Beach · 13 guests

Board our Azimut Flybridge 42' for an unforgettable experience!

5.0
$200/hour

Sailing Reviews in Caribbean

  1. EDDIE

    EDDIE

    All-Inclusive Luxury Sailing Catamaran Charter from Paradise Island

    Ignacio was a wonderful host. He creates a good game plan for the day and makes the entire ride / day comfortable for all. I would definitely use him if we travel back to Nassau. This specific vessel is also perfect for a day charter for a group of 4 or more

  2. MN

    Michael

    Cartagena Sunset & Bay Tour on a Large 38 feet Luxury Boat (Private Tour)

    The staff was really friendly and the tour was perfect so see the impressive skyline of Cartagena. I had a lot if fun on the boat. It is worth the money.

  3. PM

    Paulina

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

    My wedding anniversary brought me back here! We obtain their services and we have to say our guest and us had a blast! Very professional services, their food items were great, overall a great and fun experience!

  4. DV

    DAVID

    Janise Sailing Afternoon Charter - Fajardo, Puerto Rico 🇵🇷

    We had a fantastic day with our Captain and his team Harold! If you come to Puerto Rico this is a mandatory activity!!! It is worth every dollar….. when we come back we will do it again

  5. BB

    Brandy

    FULLY CUSTOMIZABLE Luxury Catamaran Charter

    We had Captain Fox and Jaclyn. They were both fantastic. Attentive to every detail. Food was great, we had the beef and fish burger bar, along with the fruit, meat and cheese plate, salad, pasta salad, and dessert. There was always something to eat if you wanted. The water toys were perfect to lounge and enjoy the water, along with jumping from top deck, its higher than you think so quite a little thrill. We also included a jet ski which I highly recommend, a lot of fun to add to the experience along with the famous swimming with the pigs. Even if you don’t think you’re interested, try it, we had several people with us who were on the fence whether or not they wanted to and after they did they were shocked how much they enjoyed the experience. The trick is to lure the pigs into the water and make them swim before giving them their treat. Also, we did not bring shoes because we left them on the boat but the worst thing about swimming with the pigs was the sharp rocky reef to get the pigs out far enough to swim, had I known we would have took some sort of sandal or water shoe to help from slicing your feet. Over all day was amazing. Most importantly Jaclyn was very sweet, she was little shy, but warmed up, but she was never lacking in anything we needed. Captain Fox was awesome, and fun. They both had warm personalities that made our group feel at ease and we were able to laugh and have fun with them too. Thank you both for creating a day we’ll never forget!

  6. Michael

    Michael

    Private Luxury Sailing Experience out of Old San Juan

    Had a fantastic time! Willy and David were perfect and our entire group had an incredible experience. Definitely book!!