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All listings in Caribbean

Awesome sailboat rentals in the Caribbean.

4.8
(2,354 Reviews)

Page 6 of 19439 listings

ENJOY UNLIMITED OPEN BAR TOUR 🏝️ PRIVATE CHARTER😎☀️
Events in Uvero Alto · 70 guests

ENJOY UNLIMITED OPEN BAR TOUR 🏝️ PRIVATE CHARTER😎☀️

3.7
Superowner
Best of 2026
$45/hour
ALL INCLUSIVE luxury day and overnight charter on the sailing catamaran Amura
Sailing in Nassau · 40 guests

ALL INCLUSIVE luxury day and overnight charter on the sailing catamaran Amura

5.0
$960/hour
Limited Availability
Lagoon 400 18 People Cruising Catamaran In Cartagena, Colombia
Sailing in Cartagena · 18 guests

Lagoon 400 18 People Cruising Catamaran In Cartagena, Colombia

5.0
$1,700/day
Curacao Private Sunset Tour Deluxe
Sailing in Santa Barbara Plantation · 6 guests

Curacao Private Sunset Tour Deluxe

5.0
$250/hour
Power in Las Galeras
Sailing in Las Galeras · 10 guests

Power in Las Galeras

New
$1,580/day
2025 VIP Birthday Celebration - Bachelor-bachelorette And More! Book Now!
Events in Bávaro · 100 guests

2025 VIP Birthday Celebration - Bachelor-bachelorette And More! Book Now!

New
Superowner
Best of 2026
$117/hour
Luxury Catamaran Lagoon ' Capacity up to 18
Powerboats in Cartagena · 18 guests

Luxury Catamaran Lagoon ' Capacity up to 18

5.0
Superowner
$180/hour
Punta Cana - PRIVATE SMALL GROUP (CAT PAUSE)
Sailing in Bávaro · 15 guests

Punta Cana - PRIVATE SMALL GROUP (CAT PAUSE)

5.0
$250/hour
!!Best 2025 Winner !! Power Catamaran in La Romana, Dominican Republic
Events in La Romana · 100 guests

!!Best 2025 Winner !! Power Catamaran in La Romana, Dominican Republic

5.0
Superowner
Best of 2026
$60/hour
Limited Availability
Amazing Party Boats In Puerto Plata Make Your Reservation Now
Powerboats in Puerto Plata · 100 guests

Amazing Party Boats In Puerto Plata Make Your Reservation Now

5.0
Superowner
Best of 2026
$50/hour
Private Yacht Luxury Turquoise Adventure Ocho Rios, Jamaica
Sailing in Ocho Rios · 40 guests

Private Yacht Luxury Turquoise Adventure Ocho Rios, Jamaica

5.0
$1,560/hour
Full Day. Reserve a Luxury 47' Leopard Catamaran in St. Thomas, USVI
Sailing in Charlotte Amalie · 12 guests

Full Day. Reserve a Luxury 47' Leopard Catamaran in St. Thomas, USVI

5.0
$293/hour
Beautiful 36' Sea Ray Motor Yacht up to 12 guests and floating mat in Miami!!
Powerboats in Miami · 10 guests

Beautiful 36' Sea Ray Motor Yacht up to 12 guests and floating mat in Miami!!

4.3
$100+/hour
Half Day Luxury Trips Aboard Our 47’ Sailing Yacht Catamaran
Sailing in Charlotte Amalie · 12 guests

Half Day Luxury Trips Aboard Our 47’ Sailing Yacht Catamaran

4.6
$365/hour
Limited Availability
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
🏆BEST 2025🏆Family Party Boat with Slide for from 1 to 100 people in Punta Cana
Tours in Punta Cana · 100 guests

🏆BEST 2025🏆Family Party Boat with Slide for from 1 to 100 people in Punta Cana

3.7
Superowner
Best of 2026
$50/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
60' Sailing Party Catamaran in Miami Florida
Sailing in Miami Beach · 49 guests

60' Sailing Party Catamaran in Miami Florida

4.6
$1,300/hour
Sailing and motor Catamaran for Cruising and Celebrations🎉Best 2025 Awards 🎉
Sailing in Uvero Alto · 30 guests

Sailing and motor Catamaran for Cruising and Celebrations🎉Best 2025 Awards 🎉

3.5
Superowner
Best of 2026
$100/hour
Curacao Private Romantic Sunset Tour 2p
Sailing in Santa Barbara Plantation · 2 guests

Curacao Private Romantic Sunset Tour 2p

5.0
$250/hour
Awesome and Spacious Sea Ray 55’ 2009 Motor Yacht Rental in Fajardo, Puerto Rico
Events in Fajardo · 12 guests

Awesome and Spacious Sea Ray 55’ 2009 Motor Yacht Rental in Fajardo, Puerto Rico

5.0
$800/hour
Ultimate Day Sailing Charter Onboard 40' Baba Sailboat in St. Thomas
Sailing in St. Thomas · 6 guests

Ultimate Day Sailing Charter Onboard 40' Baba Sailboat in St. Thomas

5.0
$220/hour
60 Person Catamaran, Pet Friendly - Reserve Your Day On The Water With Us!
Powerboats in Bávaro · 200 guests

60 Person Catamaran, Pet Friendly - Reserve Your Day On The Water With Us!

New
Superowner
Best of 2026
$16/hour
Luxury Sailing Catamaran Charter in Fajardo, Puerto Rico
Sailing in Fajardo · 19 guests

Luxury Sailing Catamaran Charter in Fajardo, Puerto Rico

5.0
$450/hour

Sailing Reviews in Caribbean

  1. Shawn

    Shawn

    Half Day Luxury Trips Aboard Our 47’ Sailing Yacht Catamaran

    We had a great time on the Pisces. Captain Judi and Callia were a great crew to be with. They took us to two different snorkeling spots that were great. Callia looked after us in the water and followed us to make sure we were all safe and got back to the boat. She also makes a great, and strong, Pisces punch. The Pisces was in great shape and fit my family of 10 very comfortably. Next time we are in St Thomas I will certainly book with them again.

  2. AH

    Alexx

    60ft AIcon Yacht – Perfect for Luxury Day Trips

    Wow! What a fun day! We had a large bachelorette group and had the absolute BEST day! Carlos was super communicative and his crew was fantastic. The boat was beautiful, clean, and had everything we needed for a day out on the water! Can’t recommend this boat enough!!

  3. Dana

    Dana

    Luxury Sailing Catamaran Charter in Fajardo, Puerto Rico

    Gabriela and her team are incredible! I’m happy to share that our experience was absolutely phenomenal from start to finish. East Island Excursions was incredibly professional and accommodating throughout the entire planning process. Communication was seamless, check-in was a breeze, and everything ran so smoothly on the day of our excursion. The boat itself was stunning and made the perfect backdrop for my sister’s bachelorette party—truly unforgettable. Most of all, the crew was exceptional. They were warm, welcoming, and attentive to every detail, making us feel so well taken care of. They genuinely went above and beyond to make the day feel special, and it showed in every interaction. We couldn’t have asked for a better experience and would absolutely recommend both Getmyboat and East Island Excursions to anyone looking for a memorable, stress-free adventure on the water. Thank you again for such a wonderful experience! Warmly, Dana

  4. AW

    Alexandra

    ALL INCLUSIVE luxury day and overnight charter on the sailing catamaran Amura

    Our tip was amazing! The crew was incredible and they made sure we had a great time. Rebecca's meal was wonderful! We had a blast on the jetski, visiting the pigs, and dancing, as well as being able to relax and enjoy the sun. Thank you for making sure we all had the best day. I highly recommend booking with Rebecca! Communication was great and she was so accommodating. Thank you!

  5. AW

    Alice

    ALL INCLUSIVE luxury day and overnight charter on the sailing catamaran Amura

    Rebecca and Max were excellent friendly hosts! The tour around the islands were phenomenal with the perfect amount of time between the islands and the food prepared by Rebecca was phenomenal. For a relaxing trip on a super clean and spacious cataraman, this is highly recommended.

  6. SW

    Sarah

    ALL INCLUSIVE luxury day and overnight charter on the sailing catamaran Amura

    Amura and her crew were above and beyond anything we could have hoped for in our sailing. Truly 5 star from our arrival to our departure. The day could not have been any better executed for parents and for kids… and THAT is a hard feat! First of all- no surprises, the boat is actually as amazing as it looks!! So many listings seem great but on arrival are not the case. Not here!!! The boat is in pristine condition with various areas to gather The Crew- what can we say… the kindness, patience, humor, knowledge… all of it!! They kept our champagne glasses and surf and turf plates full!! The food was top notch, from fruit, to charcuterie to our meal and dessert. Delicious!! Rebecca even helped to accommodate some dietary needs… so grateful The Day- captain Max lead us on an adventure to see the best and most beautiful parts of the Bahamas. All in all, you cannot go wrong with Amura… from the boat to the crew this is a 5 start experience from start to finish.