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All listings in Caribbean

Awesome sailboat rentals in the Caribbean.

4.8
(2,281 Reviews)

Page 3 of 19438 listings

47ft Sea Ray Yacht Rental | Miami Luxury Experience
Events in Miami · 13 guests

47ft Sea Ray Yacht Rental | Miami Luxury Experience

New
$200/hour
Fountaine Pajot Great Sailing Catamaran for up to 25 people!
Sailing in Cartagena · 25 guests

Fountaine Pajot Great Sailing Catamaran for up to 25 people!

4.5
Superowner
$1,600/day
Sailing Charter On 39' Catalina Sailboat In Fort Lauderdale, Florida
Sailing in Fort Lauderdale · 6 guests

Sailing Charter On 39' Catalina Sailboat In Fort Lauderdale, Florida

5.0
Superowner
$119+/hour
⛵️  MARIAH — 60’ CATAMARAN (UP TO 49 GUESTS)
Sailing in Miami Beach · 49 guests

⛵️ MARIAH — 60’ CATAMARAN (UP TO 49 GUESTS)

5.0
Superowner
$700+/hour
All Inclusive, Luxury 42 Lagoon Catamaran Adventure in Fajardo, Puerto Rico
Sailing in Fajardo · 12 guests

All Inclusive, Luxury 42 Lagoon Catamaran Adventure in Fajardo, Puerto Rico

5.0
$467+/hour
Exclusive Escape with Ocean Explorer Catamaran in Punta Cana
Powerboats in Uvero Alto · 30 guests

Exclusive Escape with Ocean Explorer Catamaran in Punta Cana

4.8
Superowner
Best of 2026
$16/hour
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
The Wanderlust Ultimate Catamaran Adventure
Sailing in Nassau · 12 guests

The Wanderlust Ultimate Catamaran Adventure

5.0
$630/hour
Punta Cana Booze Cruise Experience  Snorkeling • Sandbar • Music • Drinks
Events in Punta Cana · 180 guests

Punta Cana Booze Cruise Experience Snorkeling • Sandbar • Music • Drinks

4.0
Superowner
Best of 2026
$17/hour
Sail In Caribbean Paradise with Jeanneau Sun Odyssey 44
Sailing in Jolly Harbour · 6 guests

Sail In Caribbean Paradise with Jeanneau Sun Odyssey 44

4.9
$280/day
⛵️ Catamaran 49-Person Party Boat Includes: 1-Captain, 1-Mate and 1-Bartender
Sailing in Miami Beach · 49 guests

⛵️ Catamaran 49-Person Party Boat Includes: 1-Captain, 1-Mate and 1-Bartender

5.0
Superowner
$700+/hour
🏝️Exciting Private Yacht: Affordable Charter with Crew🎉
Events in Punta Cana · 250 guests

🏝️Exciting Private Yacht: Affordable Charter with Crew🎉

3.0
Superowner
Best of 2026
$17/hour
Beautiful Cruising Catamaran for Up to 20 Friends in Cartagena, Colombia
Sailing in Cartagena · 20 guests

Beautiful Cruising Catamaran for Up to 20 Friends in Cartagena, Colombia

4.8
Superowner
$900/day
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
3.5hr Catamaran Experience Montego Bay
Sailing in Montego Bay · 30 guests

3.5hr Catamaran Experience Montego Bay

5.0
Superowner
$834/hour
Private Luxury Bali 4.0 Catamaran with 3 Cabin from Old San Juan
Sailing in San Juan · 12 guests

Private Luxury Bali 4.0 Catamaran with 3 Cabin from Old San Juan

5.0
$575/hour
Sailing From Pompano Beach, FL
Sailing in Pompano Beach · 12 guests

Sailing From Pompano Beach, FL

4.6
Superowner
$125+/hour
45' Sea Ray Yacht Charter in Turks & Caicos
Powerboats in The Bight Settlement · 15 guests

45' Sea Ray Yacht Charter in Turks & Caicos

5.0
$500/hour
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
Exclusive Private boat rental to any occasion in punta cana🥳
Events in El Cortecito · 30 guests

Exclusive Private boat rental to any occasion in punta cana🥳

New
Superowner
Best of 2026
$10/hour
3hr Classic Yacht Experience Montego Bay
Powerboats in Montego Bay · 25 guests

3hr Classic Yacht Experience Montego Bay

5.0
Superowner
$933/hour
⛵️ Catamaran Party Boat with Captain & Crew – Up to 42 Guests!
Sailing in Miami Beach · 42 guests

⛵️ Catamaran Party Boat with Captain & Crew – Up to 42 Guests!

4.8
Superowner
$700+/hour
2.5hr Catamaran Experience Montego Bay
Events in Montego Bay · 30 guests

2.5hr Catamaran Experience Montego Bay

5.0
Superowner
$995/hour
Let's go Sailing in Miami!
Sailing in Miami · 6 guests

Let's go Sailing in Miami!

5.0
$45+/hour

Sailing Reviews in Caribbean

  1. CL

    Catherine

    All Inclusive, Luxury 42 Lagoon Catamaran Adventure in Fajardo, Puerto Rico

    5/5 star experience. I’m really happy to have chosen Minell and her team for my birthday celebration. Really lovely captain and crew to work with and nothing more I could have asked for from the all-inclusive experience with food, drink, and equipment for chilling and exploring the seas. Thank you!

  2. KP

    Keith

    Sail In Caribbean Paradise with Jeanneau Sun Odyssey 44

    Great day on the water with Joshua and Kieran. The boat was in great shape, and had all the amenities we could enjoy. The crew worked with us on a great itinerary for the day and we enjoyed the experience. Everything was as advertised and worked perfectly, would recommend.

  3. MH

    Maggie

    Beautiful Cruising Catamaran for Up to 20 Friends in Cartagena, Colombia

    We had an amazing time! The crew was fantastic and the boat was perfect for what we needed. Thank you!!

  4. SP

    Sruti

    60ft AIcon Yacht – Perfect for Luxury Day Trips

    Amazing experience!! Would definitely recommend- was the highlight of my bachelorette weekend!!! Crew was so nice and the boat was gorgeous

  5. SM

    Sanjay

    Sail In Caribbean Paradise with Jeanneau Sun Odyssey 44

    Awesome trip with one of Ed’s boats in Antigua. Great boat conditions and amenities. Very friendly and flexible skipper and first mate. Super experience over all. Would certainly charter boats again through him.

  6. Kathy

    Kathy

    Sailing Charter On 39' Catalina Sailboat In Fort Lauderdale, Florida

    A glorious day at sea! Do yourself a favor and book this experience! You won’t regret it! Feeling at ease on the water and really enjoying the element was what were were striving for! As a local realtor, I make sure to enjoy what this beautiful place has to offer and this is one of them!