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All listings in Caribbean

Awesome sailboat rentals in the Caribbean.

4.7

(2,379 Reviews)

Page 10 of 19 • 439 listings

🛥️🏝️ SAIL IN PUNTA CANA PRIVATE GROUPS 🛥️🏝️

Tours in Dominican Republic · 40 guests

🛥️🏝️ SAIL IN PUNTA CANA PRIVATE GROUPS 🛥️🏝️

New

Superowner

Best of 2026

$75/hour

Luxury 52 Catamaran With AC - Price include 2 People

Sailing in Guna Yala Comarca · 8 guests

Luxury 52 Catamaran With AC - Price include 2 People

5.0

$2,700/day

Private 40ft Catamaran Charter to Rosario Islands, Cartagena

Sailing in Cartagena · 18 guests

Private 40ft Catamaran Charter to Rosario Islands, Cartagena

New

$500/hour

Instant Book

Punta Cana Booze Shared Cruise, Snorkeling and Sand-Bar (Only adults)

Events in Bávaro · 100 guests

Punta Cana Booze Shared Cruise, Snorkeling and Sand-Bar (Only adults)

5.0

$240/hour

Maxicat 65ft Private Party Catamaran in Cartagena

Sailing in Cartagena · 80 guests

Maxicat 65ft Private Party Catamaran in Cartagena

New

Superowner

$838/hour

Cruising Catamaran Rental in Puerto Plata, Puerto Plata

Sailing in Barrio Las Yaguitas · 80 guests

Cruising Catamaran Rental in Puerto Plata, Puerto Plata

1.0

Superowner

Best of 2026

$183/hour

Puerto Plata Luxury Catamaran Charter with Snorkeling & Lunch

Powerboats in Sosúa · 70 guests

Puerto Plata Luxury Catamaran Charter with Snorkeling & Lunch

New

$242/hour

Instant Book

An amazing charter experience - Lagoon 44 Cruising Catamaran in Cartagena

Sailing in Cartagena · 23 guests

An amazing charter experience - Lagoon 44 Cruising Catamaran in Cartagena

New

Superowner

$231/hour

Punta Cana - FAMILY BOAT

Sailing in Bávaro · 200 guests

Punta Cana - FAMILY BOAT

New

$160/hour

42' Luxury Catamaran Sailboat

Sailing in Miami · 12 guests

42' Luxury Catamaran Sailboat

New

$300/hour

Dunn’s River Falls Private Catamaran Cruise – Ocho Rios

Powerboats in Ocho Rios · 100 guests

Dunn’s River Falls Private Catamaran Cruise – Ocho Rios

New

$654/hour

Unforgettable Private Sunset Cruise in Punta Cana - Luxury VIP Boat Experience

Events in Sosúa · 25 guests

Unforgettable Private Sunset Cruise in Punta Cana - Luxury VIP Boat Experience

New

$135/hour

Have an amazing time on Maxi Cat 65 Cruising Catamaran in Cartagena, Colombia

Sailing in Cartagena · 80 guests

Have an amazing time on Maxi Cat 65 Cruising Catamaran in Cartagena, Colombia

New

Superowner

$5,000/day

Montego Bay Private Catamaran Cruise with Open Bar & Snorkeling

Sailing in Montego Bay · 60 guests

Montego Bay Private Catamaran Cruise with Open Bar & Snorkeling

New

$1,176/hour

Limited Availability

57' Fountaine Pajot Sailing Catamaran - A Luxury Experience

Sailing in Fort Lauderdale · 12 guests

57' Fountaine Pajot Sailing Catamaran - A Luxury Experience

5.0

$450/hour

Charter the yacht of your dreams Jeanneau 54 Cruising Monohull in Cartagena

Sailing in Cartagena · 14 guests

Charter the yacht of your dreams Jeanneau 54 Cruising Monohull in Cartagena

New

Superowner

$200/hour

Champagne Sunset Cruise – Private Catamaran (5:00 PM – 7:00 PM)

Sailing in El Cortecito · 70 guests

Champagne Sunset Cruise – Private Catamaran (5:00 PM – 7:00 PM)

New

$644/hour

Instant Book

Ocho Rios Private Sunset Catamaran with Dinner & Open Bar

Powerboats in Ocho Rios · 100 guests

Ocho Rios Private Sunset Catamaran with Dinner & Open Bar

New

$817/hour

Punta Cana Sunset Catamaran Cruise with BBQ, Champagne & Music

Sailing in Bávaro · 70 guests

Punta Cana Sunset Catamaran Cruise with BBQ, Champagne & Music

New

$500/hour

Instant Book

Bahia de las Aguilas- Private Catamaran Cruise

Events in Dominican Republic · 70 guests

Bahia de las Aguilas- Private Catamaran Cruise

New

$500/hour

39ft Sea Ray Motor Yacht in Punta Cana, La Altagracia

Events in Bávaro · 12 guests

39ft Sea Ray Motor Yacht in Punta Cana, La Altagracia

New

$1,910/day

Sail from Boynton Beach to Lake Boca

Sailing in Boynton Beach · 12 guests

Sail from Boynton Beach to Lake Boca

New

Superowner

$126+/hour

Hit the water on Beneteau 50 Cruising Monohull in Cartagena, Colombia

Sailing in Cartagena · 12 guests

Hit the water on Beneteau 50 Cruising Monohull in Cartagena, Colombia

New

Superowner

$150/hour

Private 41ft Lounge Catamaran Charter in Aruba for Up to 45 Guests

Sailing in Oranjestad-West · 45 guests

Private 41ft Lounge Catamaran Charter in Aruba for Up to 45 Guests

New

$800/hour

Instant Book

Top Destinations Nearby

Sailing Reviews in Caribbean

DP
Dawn

Luxury 52 Catamaran With AC - Price include 2 People
⭐⭐⭐⭐⭐ An unforgettable experience in San Blas, Panama! The Italian-owned boat exceeded all expectations. The food was divine, reflecting true Italian finesse, and the service was impeccable. Every moment aboard was filled with warmth, comfort, and authentic hospitality. A must-try for anyone seeking a remarkable sailing adventure in paradise!
Evan

Punta Cana Booze Shared Cruise, Snorkeling and Sand-Bar (Only adults)
Amazing people to deal with ! Highly recommend
erkan

57' Fountaine Pajot Sailing Catamaran - A Luxury Experience
Crew , boat , owner … they were the best !

Real reviews from happy Getmyboaters.

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