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All listings in Caribbean

Awesome sailboat rentals in the Caribbean.

4.8
(2,245 Reviews)

Page 3 of 19433 listings

Leopard 47 PC Power Catamaran Charter in Castries, St Lucia
Events in Castries · 8 guests

Leopard 47 PC Power Catamaran Charter in Castries, St Lucia

5.0
$408/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
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
47ft Sea Ray Yacht Rental | Miami Luxury Experience
Events in Miami · 13 guests

47ft Sea Ray Yacht Rental | Miami Luxury Experience

New
$200/hour
Private Tours- Snorkeling at Palomino & Beach Time at Icacos Island- Mako 29'
Tours in Fajardo · 6 guests

Private Tours- Snorkeling at Palomino & Beach Time at Icacos Island- Mako 29'

5.0
Superowner
Best of 2026
$675/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
⛵️ 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
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
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
⛵️  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
🏝️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
The Wanderlust Ultimate Catamaran Adventure
Sailing in Nassau · 12 guests

The Wanderlust Ultimate Catamaran Adventure

5.0
$636/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
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
3.5hr Catamaran Experience Montego Bay
Sailing in Montego Bay · 30 guests

3.5hr Catamaran Experience Montego Bay

5.0
Superowner
$834/hour
Sailing From Pompano Beach, FL
Sailing in Pompano Beach · 12 guests

Sailing From Pompano Beach, FL

4.6
Superowner
$125+/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
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
$1,152/day
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
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
2.5hr Catamaran Experience Montego Bay
Events in Montego Bay · 30 guests

2.5hr Catamaran Experience Montego Bay

5.0
Superowner
$995/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
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. 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

  4. EA

    Eunice

    Private Tours- Snorkeling at Palomino & Beach Time at Icacos Island- Mako 29'

    We had a great time - captain Jorge was amazing- very attentive and so friendly- got us there safely and took us to both islands Food, snacks and beverages were great as listed! Would recommend and use them in the future

  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. Jacob

    Jacob

    Private Tours- Snorkeling at Palomino & Beach Time at Icacos Island- Mako 29'

    José and first mate were phenomenal! Seas were a little choppy on the ride over but the ride was very smoother as they had the bow trimmed up. Lunch, snorkeling, swimming, fishing - couldn’t ask for more for us and our four year old. They watched him and fished while my wife and I snorkeled.