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All listings in Caribbean

Awesome sailboat rentals in the Caribbean.

4.8
(2,320 Reviews)

Page 6 of 19433 listings

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
Amazing Punta Cana Sand Bar Party with Chaparral Motor Yacht!
Events in Bávaro · 200 guests

Amazing Punta Cana Sand Bar Party with Chaparral Motor Yacht!

5.0
Superowner
Best of 2026
$17/hour
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
Fort Lauderdale - Bahamas Sailing Charters
Sailing in Fort Lauderdale · 6 guests

Fort Lauderdale - Bahamas Sailing Charters

5.0
$130+/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
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
Luxury Catamaran Lagoon ' Capacity up to 18
Powerboats in Cartagena · 18 guests

Luxury Catamaran Lagoon ' Capacity up to 18

5.0
Superowner
$180/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
$577/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
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
🏆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
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

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. Perlicia

    Perlicia

    Amazing Punta Cana Sand Bar Party with Chaparral Motor Yacht!

    Everything was nice!! Crew was awesome!!!

  4. LE

    Lia

    Fort Lauderdale - Bahamas Sailing Charters

    Truly incredible experience with Jose and Alex. Absolutely magical adventure and highly recommended to anyone looking for an unforgettable time. The food was also out of this world and so much attention to detail in every moment. We will absolutely be back and everyone needs to experience this.

  5. Sofia

    Sofia

    Fort Lauderdale - Bahamas Sailing Charters

    Wow, this was an incredible experience for a very reasonable price. Jose and Alexandria’s hospitality and generosity is unmatched. I left the boat with two new friends, and I will definitely be keeping their information for future trips. We did a trip around Fort Lauderdale, and we were lucky enough to see some dolphins! We swam around in the beautiful and refreshing water and we had some incredible snacks, wellness drinks, and a meal at the end. All very healthy, and we left the boat feeling much better than we did when we got on. That’s the power of high quality, healthy food. Everything about this trip was amazing, but I must say the best part was their kindness. They took great care of me and my friends. Wonderful people and a very impressive boat!

  6. AH

    Andrew

    Fort Lauderdale - Bahamas Sailing Charters

    I cannot overstate how wonderful our afternoon sail was with Jose and Luke. The weather was perfect, the boat in correct order, and each phase of the experience was conducted seamlessly. With that said, the calming center of the day - and by far the main reason we had such a special time -was Jose. Every once in a while, you meet a special person who has mastered their craft, acts as an enthusiastic and patient instructor, while making sure each person was comfortable and happy. For some, sailing can be intimidating, especially when the wind and waves act up. Jose was 'present' every moment to show us the joys of switching from power to wind, with confidence and professionalism. While we have charted powerboats and sailboats, this particular experience is not to be missed. He even prepared us healthy, vegan food once we returned to dock, showing us being in nature, enjoying the sea, and having yummy healthy food is all part of finding some momentary tranquility. Book this experience! I know we will again.