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All listings in Caribbean

Awesome sailboat rentals in the Caribbean.

4.8
(2,309 Reviews)

Page 6 of 18426 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
Luxury Catamaran Lagoon ' Capacity up to 18
Powerboats in Cartagena · 18 guests

Luxury Catamaran Lagoon ' Capacity up to 18

5.0
Superowner
$180/hour
Half Day 50' Private Sailing Catamaran. Luxury, Beach/Snorkel. Departs Red Hook
Sailing in St. Thomas · 12 guests

Half Day 50' Private Sailing Catamaran. Luxury, Beach/Snorkel. Departs Red Hook

4.9
$390/hour
Marlowe Hunter 33’ Sailing in Fort Lauderdale
Sailing in Fort Lauderdale · 6 guests

Marlowe Hunter 33’ Sailing in Fort Lauderdale

5.0
$90+/hour
Leopard 53 Power Cat (25-ft wide deck space) + massive water hammock
Powerboats in Fort Lauderdale · 12 guests

Leopard 53 Power Cat (25-ft wide deck space) + massive water hammock

New
$367+/hour
Fort Lauderdale - Bahamas Sailing Charters
Sailing in Fort Lauderdale · 6 guests

Fort Lauderdale - Bahamas Sailing Charters

5.0
$130+/hour
Saint Kitts Private Boat Charter
Tours in Basseterre · 55 guests

Saint Kitts Private Boat Charter

5.0
$300/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
Exclusive Day Sail on a Private Beneteau Oceanis 440 Sailboat
Sailing in Gros Islet · 10 guests

Exclusive Day Sail on a Private Beneteau Oceanis 440 Sailboat

New
$576/day
48 Ft Catamaran sailing on the Biscayne Bay . Party, Sound healing, Wingfoil
Sailing in Miami · 13 guests

48 Ft Catamaran sailing on the Biscayne Bay . Party, Sound healing, Wingfoil

5.0
$187+/hour
Power in Las Galeras
Sailing in Las Galeras · 10 guests

Power in Las Galeras

New
$1,580/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
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
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
Curacao Private Sunset Tour Deluxe
Sailing in Santa Barbara Plantation · 6 guests

Curacao Private Sunset Tour Deluxe

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

Cruising Monohull Charter in Samaná, Dominican Republic

4.0
$1,586/day
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
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 Jan Thiel · 2 guests

Curacao Private Romantic Sunset Tour 2p

5.0
$250/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. KF

    Katisha

    Lagoon 400 18 People Cruising Catamaran In Cartagena, Colombia

    José and team were wonderful. They were responsive, accommodating and went the extra mile to make my clients 40th Birthday a great one! Will definitely use them in the future.

  3. BC

    Brian

    Half Day 50' Private Sailing Catamaran. Luxury, Beach/Snorkel. Departs Red Hook

    Lovely half day exploring the USVI's - the boat was great and spacious, and the crew charted an efficient course to see as much as possible, while also fitting in water activity/snorkeling. The crew was kind, professional, and incredibly accommodating, highly recommend!

  4. Patrick

    Patrick

    Half Day 50' Private Sailing Catamaran. Luxury, Beach/Snorkel. Departs Red Hook

    Fantastic experience with Capt Rachel and soon to be Capt Valy. They let us decide the itinerary and we visited Caneel Bay, Christmas Cove and Pizza Pi, with some nice sailing in between. The vessel was spotless and the crew was incredibly professional. Highest recommendation.

  5. RH

    Renata

    Half Day 50' Private Sailing Catamaran. Luxury, Beach/Snorkel. Departs Red Hook

    Myself and 9 of my friends booked the yacht with Captain Scott aka Captain Splash. Prior to the trip he answered every one of my questions. Upon arrival he and Osay were very accommodating! He allowed us to bring refreshments and snacks. We were able to connect to the bluetooth and listen to music. We got off the yacht to go snorkeling and saw both fish and turtles underwater. Captain Scott was extremely hospitable, friendly and I would definitely recommend this excursion to anyone! My only regret is not getting a full day!

  6. AM

    Aysia

    Half Day 50' Private Sailing Catamaran. Luxury, Beach/Snorkel. Departs Red Hook

    Loved every minute! They were on time picking up, so nice and helpful! Got us anything any everything we needed while on board. We were able to play our own music, swim, snorkel, And visited honeymoon beach. I really appreciated them letting us have our fun and showing us a good time! I would definitely book with you all next time we travel back here! Thank you!