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All listings in Caribbean

Awesome sailboat rentals in the Caribbean.

4.8
(2,357 Reviews)

Page 3 of 19440 listings

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
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
“Exclusive Escape, Unlimited Adventure on our Yacht”
Events in Miami · 13 guests

“Exclusive Escape, Unlimited Adventure on our Yacht”

5.0
$250/hour
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
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
47ft Sea Ray Yacht Rental | Miami Luxury Experience
Events in Miami · 13 guests

47ft Sea Ray Yacht Rental | Miami Luxury Experience

New
$200/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
🏝️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
$45/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
⛵️  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
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
3.5hr Catamaran Experience Montego Bay
Sailing in Montego Bay · 30 guests

3.5hr Catamaran Experience Montego Bay

5.0
Superowner
$834/hour
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
Lagoon 38 Catamaran trip in St Martin with skipper, departure from Orient bay
Sailing in Saint Martin · 12 guests

Lagoon 38 Catamaran trip in St Martin with skipper, departure from Orient bay

4.9
$1,161/day
Private Luxury Catamaran - Old San Juan
Sailing in San Juan · 12 guests

Private Luxury Catamaran - Old San Juan

5.0
$575/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

4.7
Superowner
$900/day
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
$475/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
⛵️ 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
Janise Sailing Afternoon Charter - Fajardo, Puerto Rico 🇵🇷
Sailing in Fajardo · 6 guests

Janise Sailing Afternoon Charter - Fajardo, Puerto Rico 🇵🇷

4.9
$995/day
Let's go Sailing in Miami!
Sailing in Miami · 6 guests

Let's go Sailing in Miami!

5.0
$45+/hour
3hr Classic Yacht Experience Montego Bay
Powerboats in Montego Bay · 25 guests

3hr Classic Yacht Experience Montego Bay

5.0
Superowner
$933/hour

Sailing Reviews in Caribbean

  1. JB

    Jason

    Lagoon 38 Catamaran trip in St Martin with skipper, departure from Orient bay

    Great catamaran trip that had everything a group could need. Demanez is a wonderful host, he took us to all the great spots around Saint Martin, was very knowledgeable, and never made us feel rushed. Would highly recommend a trip with Demanez!

  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. 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.

  4. 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!!

  5. JB

    John

    Lagoon 38 Catamaran trip in St Martin with skipper, departure from Orient bay

    Loved our two family excursion around St. Martin! Kids loved the big floating mat. Adults liked being on the ocean and snorkeling creole rock

  6. MB

    Meaghan

    Private Luxury Catamaran - Old San Juan

    Am absolute must when visiting Old San Juan! The boat is clean, spacious, and the crew is wonderful. This will be a regular occurence on our trips to PR now!