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All listings in Caribbean

Awesome sailboat rentals in the Caribbean.

4.7
(2,411 Reviews)

Page 4 of 20 • 460 listings

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
40ft Fountaine Pajot Lucia 40 Catamaran for Snorkeling in Saint George, Grenada
Sailing in Saint George's · 10 guests

40ft Fountaine Pajot Lucia 40 Catamaran for Snorkeling in Saint George, Grenada

New
$250/hour
Sailing From Pompano Beach, FL
Sailing in Pompano Beach · 12 guests

Sailing From Pompano Beach, FL

4.6
Superowner
$125+/hour
Let's go Sailing in Miami!
Sailing in Miami · 6 guests

Let's go Sailing in Miami!

5.0
$45+/hour
Janise Sailing Afternoon Charter - Fajardo, Puerto Rico 🇵🇷
Sailing in Fajardo · 6 guests

Janise Sailing Afternoon Charter - Fajardo, Puerto Rico 🇵🇷

4.9
$995/day
🏆🎉LUXURY YACHT RENTED BY OWNER- Best 2025- 2026 Awards TOTALLY PRIVATE 🎉
Events in Verón · 100 guests

🏆🎉LUXURY YACHT RENTED BY OWNER- Best 2025- 2026 Awards TOTALLY PRIVATE 🎉

4.8
Superowner
Best of 2026
$50/hour
Lux Catamaran Fountaine Pajot 40ft
Sailing in Leeward Settlement · 10 guests

Lux Catamaran Fountaine Pajot 40ft

New
$714+/hour
Sea Ray Sundancer 38ft – Classic Luxury Cruise in Miami!
Events in Miami · 13 guests

Sea Ray Sundancer 38ft – Classic Luxury Cruise in Miami!

5.0
$100/hour
Private Sailing Full Day Charter - Fajardo, Puerto Rico
Sailing in Fajardo · 6 guests

Private Sailing Full Day Charter - Fajardo, Puerto Rico

5.0
$1,995/day
Saint Kitts Private Boat Charter
Tours in Basseterre · 55 guests

Saint Kitts Private Boat Charter

5.0
$300/hour
 46' Oyster Sailboat in St. Thomas, Virgin Islands
Sailing in St. Thomas · 6 guests

46' Oyster Sailboat in St. Thomas, Virgin Islands

5.0
$197+/hour
🥂AMAZING PRIVATE YACHT🥂
Powerboats in La Romana · 50 guests

🥂AMAZING PRIVATE YACHT🥂

5.0
Superowner
Best of 2026
$50/hour
🏆BEST 2026🏆 BOOZE CRUISE SAND BAR PUNTA CANA SNORKELING BAR ENTERTAINMENT
Events in Punta Cana · 100 guests

🏆BEST 2026🏆 BOOZE CRUISE SAND BAR PUNTA CANA SNORKELING BAR ENTERTAINMENT

4.4
Superowner
Best of 2026
$17/hour
DELUXE BOAT FOR PRIVATE VIP BACHELORETTE/BIRTHDAY PARTY
Events in Uvero Alto · 80 guests

DELUXE BOAT FOR PRIVATE VIP BACHELORETTE/BIRTHDAY PARTY

4.5
$50/hour
Sailing & Snorkeling Day Charter - Fajardo, Puerto Rico
Sailing in Fajardo · 6 guests

Sailing & Snorkeling Day Charter - Fajardo, Puerto Rico

5.0
$1,395/day
34ft Pacific Seacraft Sailboat for full day Trip in Santa Marta, Magdalena
Sailing in Santa Marta · 12 guests

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

5.0
$100/hour
Curacao Private Romantic Sunset Tour 2p
Sailing in Jan Thiel · 2 guests

Curacao Private Romantic Sunset Tour 2p

5.0
$250/hour
Luxury Lagoon 48 Catamaran — Private Charter to Icacos, Palomino & Culebra
Sailing in Fajardo · 12 guests

Luxury Lagoon 48 Catamaran — Private Charter to Icacos, Palomino & Culebra

New
$584+/hour
Get ready for the ultimate cruise in Punta Cana
Events in Macao · 150 guests

Get ready for the ultimate cruise in Punta Cana

New
Superowner
Best of 2026
$17/hour
Sunset Sail in Bay of Santa Marta, Magdalena
Sailing in Santa Marta · 12 guests

Sunset Sail in Bay of Santa Marta, Magdalena

5.0
$125/hour
50' Party Boat Catamaran in Miami  - 4 Hour Minimum - Up to 42 Guests
Sailing in Miami Beach · 42 guests

50' Party Boat Catamaran in Miami - 4 Hour Minimum - Up to 42 Guests

4.8
$1,200/hour
Luxury Beneteau Sense 55 Sailing Yacht Rental in George Town, Cayman Islands
Sailing in George Town · 20 guests

Luxury Beneteau Sense 55 Sailing Yacht Rental in George Town, Cayman Islands

5.0
$425/hour
CATALINA ISLAND  RIDE TURN UP ENTERTAINMENT SUNSET PARTY AND MORNING ADVENTURES
Events in La Altagracia · 60 guests

CATALINA ISLAND RIDE TURN UP ENTERTAINMENT SUNSET PARTY AND MORNING ADVENTURES

4.7
Superowner
Best of 2026
$13/hour
sunbathe and relax on our island in the middle of the ocean
Events in Punta Cana · 100 guests

sunbathe and relax on our island in the middle of the ocean

3.7
Superowner
Best of 2026
$50/hour

Sailing Reviews in Caribbean

  1. MG

    Misty

    Sailing & Snorkeling Day Charter - Fajardo, Puerto Rico

    Captain Ivan and mate Monica, by far exceeded our expectations. They asked what we wanted to prioritize in our trip and then created our itinerary around it. Communication from booking to the morning of was very detailed. Food and snacks were fresh and we loved the bbq and sides! If you’re searching for an incredible day stop here and BOOK! This IS the private excursion you’re looking for.

  2. AH

    Anais

    Sailing & Snorkeling Day Charter - Fajardo, Puerto Rico

    We had such an amazing experience with Captain and Ashley! They were incredibly accommodating and attentive throughout the entire trip. Some of my friends suffer from seasickness, but thankfully, they were so thoughtful and attentive that everyone felt great and was able to fully enjoy the experience.

  3. 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!!

  4. IL

    Iryna

    Let's go Sailing in Miami!

    What an amazing day we had celebrating my dad's birthday! We spent the day sailing and trying out paddle boarding, and Captain Rod made the experience even more enjoyable with his friendliness and great service. The food we ordered was absolutely delicious too!

  5. WD

    Wayne

    Let's go Sailing in Miami!

    Steve and Rodrigo were great start to finish! Our goal was to build on our sailing experience, and they are both great teachers, letting us take the helm as much as we wanted and providing tons of useful insight. Not to mention they're both good guys, and we'd absolutely recommend them for any kind of outing you have in mind.

  6. CR

    Cara

    Let's go Sailing in Miami!

    I highly recommend Captain Steven and Rodrigo for your boating needs. Spending the afternoon on their 40ft sailboat, Mystiko, was a slice of heaven…we could not have asked for a better experience. They found a perfect spot to let our family take a swim, had an amazing playlist that set the mood, and they organized an absolutely incredible charcuterie board and steak/salmon barbecue for my sister’s birthday. It was positively sublime. Thank you, Captain Steven and Rodrigo!