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All listings in Caribbean

Awesome sailboat rentals in the Caribbean.

4.8
(294 Reviews)

Page 1 of 120 listings

Enjoy Luxury Catamaran for Islands, Sunsets and Night Events
Sailing in Cartagena · 20 guests

Enjoy Luxury Catamaran for Islands, Sunsets and Night Events

5.0
Superowner
$155+/hour
Instant Book
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
The Midnight Sun,  Affordable Luxury  motor yacht
Events in Oranjestad-East · 15 guests

The Midnight Sun, Affordable Luxury motor yacht

5.0
Superowner
Best of 2025
$450/hour
Instant Book
The Ultimate Catamaran Party Boat | Up to 49 Passengers!
Events in Miami · 49 guests

The Ultimate Catamaran Party Boat | Up to 49 Passengers!

4.8
Superowner
Best of 2025
$900/hour
Instant Book
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
Sunset Sail in Bay of Santa Marta, Magdalena
Sailing in Comuna 2 · 12 guests

Sunset Sail in Bay of Santa Marta, Magdalena

5.0
$125/hour
Instant Book
Let's go Sailing in Miami!
Sailing in Miami · 6 guests

Let's go Sailing in Miami!

5.0
Superowner
$45+/hour
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
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
Fll Sun Deck 24' Final Price No Hidden Fees 10ppl max
Powerboats in Fort Lauderdale · 6 guests

Fll Sun Deck 24' Final Price No Hidden Fees 10ppl max

4.8
Superowner
$113+/hour
Instant Book
Sailing Catamaran Yacht for up to 24 Guests in Aruba
Sailing in Oranjestad-West · 24 guests

Sailing Catamaran Yacht for up to 24 Guests in Aruba

4.5
Superowner
Best of 2025
$600/hour
Instant Book
21ft Sun Tracker 20 Party Barge {Catch a Vibe}
Powerboats in Fort Lauderdale · 6 guests

21ft Sun Tracker 20 Party Barge {Catch a Vibe}

5.0
$100/hour
Instant Book
Catamaran Party Boat 42-people Includes: 1-Captain, 1-Mate and 1-Bartender
Sailing in Miami · 42 guests

Catamaran Party Boat 42-people Includes: 1-Captain, 1-Mate and 1-Bartender

3.0
Superowner
Best of 2025
$850/hour
Instant Book
44' Wellington Sailing Yacht In Antigua
Sailing in Jolly Harbour · 6 guests

44' Wellington Sailing Yacht In Antigua

5.0
$100/hour
Instant Book
Catamaran 48 foot luxury sailing cat daily, over night and weekly Excursions
Sailing in Fort Myers Beach · 12 guests

Catamaran 48 foot luxury sailing cat daily, over night and weekly Excursions

5.0
$300/hour
Instant Book
Sailing Adventure on Bay in Miami on Tartan Sailboat!
Sailing in Key Biscayne · 4 guests

Sailing Adventure on Bay in Miami on Tartan Sailboat!

5.0
$100/hour
Instant Book
Sail Miami! Beautiful Beneteau 43 Cruising Monohull
Sailing in Miami · 6 guests

Sail Miami! Beautiful Beneteau 43 Cruising Monohull

New
$180/hour
Instant Book
Lagoon 42 Cruising Catamaran for rental
Sailing in Le Marin · 12 guests

Lagoon 42 Cruising Catamaran for rental

New
$153/hour
Instant Book
65ft Searay Power Mega Yacht Rental in Miami, Florida
Sailing in Miami · 13 guests

65ft Searay Power Mega Yacht Rental in Miami, Florida

New
$450/hour
Instant Book
Amazing beautifully crafted 40-foot-private day sail excursions in St John,USVI
Sailing in Charlotte Amalie West · 6 guests

Amazing beautifully crafted 40-foot-private day sail excursions in St John,USVI

New
$250/hour
Instant Book

Sailing Reviews in Caribbean

  1. AC

    Anne

    44' Wellington Sailing Yacht In Antigua

    Amazing experience; writing my review 3 years later, because I came back to Antigua and want to book with Captain Christian again (didn’t realize I forgot to leave a review at the time)! Don’t hesitate to book, Christian and Jess were wonderful!!!

  2. BD

    Bill

    All-Inclusive Luxury Sailing Catamaran Charter from Paradise Island

    If you want a fun and safe cruise on a clean and well maintained luxury vessel, Ignacio is your man! Very professional, great communicator and tremendously experienced. Also, don't miss a tremendous culinary experience with his chef/crew/wife who is simply a doll. We loved everything about out trip and would highly recommend Ignacio to anyone interested in a luxurious cruise!

  3. DG

    Darla

    21ft Sun Tracker 20 Party Barge {Catch a Vibe}

    Our group of 6 had the BEST time with Captain Porshia! The communication was phenomenal, she called the day before to discuss our desired itinerary, meet location, and any needs we may have. We had a prompt departure, and Porshia was very knowledgeable of boating and the area. Porshia was not only friendly but also very helpful and made sure all of our needs were taking care of. 10/10… HIGHLY RECOMMEND!!! We will definitely be back.

  4. Kendra

    Kendra

    Enjoy Luxury Catamaran for Islands, Sunsets and Night Events

    Amory and is crew was amazing! This catamaran was the most beautiful I have been on. I’m trip was nothing short of amazing. His response was prompt and he was very helpful with my requests. I highly recommend this boat!!

  5. Sara

    Sara

    Enjoy Luxury Catamaran for Islands, Sunsets and Night Events

    I booked the boat tour to celebrate my surprise wedding in Cartagena. It was a great experience and so much fun! The crew was so helpful and considerate. There was more than enough room for everyone. Such a highlight from our trip. Highly recommended!

  6. VK

    Valentina

    Enjoy Luxury Catamaran for Islands, Sunsets and Night Events

    Amory was great with all communications,helped to reschedule trip due to bad weather and was in control untill we arrived back to marina. The crew very nice,accomodating and helpful.The boat very nice ,as described.We had great time ,thank you very much.