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All listings in Caribbean

Awesome sailboat rentals in the Caribbean.

4.8

(2,245 Reviews)

Page 18 of 19 • 433 listings

Jamaican Party Boat In Punta Cana Noahs Ark

Sailing in Bávaro · 50 guests

Jamaican Party Boat In Punta Cana Noahs Ark

New

$265/hour

Explore the British Virgin Islands on a Boston Whaler

Powerboats in Wickhams Cay 1 · 10 guests

Explore the British Virgin Islands on a Boston Whaler

New

$2,400/day

Luxury Sailing Experience – The Ultimate Caribbean Adventure

Sailing in Cruz Bay · 6 guests

Luxury Sailing Experience – The Ultimate Caribbean Adventure

New

$250/hour

Beneteau Oceanis Yacht 62 - Miami Charter with Captain for up to 10 Guests

Sailing in North Bay Village · 10 guests

Beneteau Oceanis Yacht 62 - Miami Charter with Captain for up to 10 Guests

New

$800+/hour

7 Day Cruise aboard Lagoon 470 Cruising Catamaran in Sainte-Anne

Sailing in Grande-Terre · 8 guests

7 Day Cruise aboard Lagoon 470 Cruising Catamaran in Sainte-Anne

New

$1,164/day

Beneteau First 40.7 Cruising Monohull - up to 6 people in Antigua and Barbuda

Sailing in English Harbour · 6 guests

Beneteau First 40.7 Cruising Monohull - up to 6 people in Antigua and Barbuda

5.0

$920/day

Bavaria 50 CR / 2013 Yacht in Saint Lucia Rodney Bay Marina

Sailing in Gros Islet · 8 guests

Bavaria 50 CR / 2013 Yacht in Saint Lucia Rodney Bay Marina

New

$729/night

Boston Whaler Center Console Rental in Road Town, Tortola

Powerboats in Wickhams Cay 1 · 10 guests

Boston Whaler Center Console Rental in Road Town, Tortola

New

$2,400/day

Charter a Cruising Monohull in Foster Hall, Barbados

Sailing in Less Beholden · 15 guests

Charter a Cruising Monohull in Foster Hall, Barbados

New

$10,667/day

"Monocoque" Sailboat's - 8 Days / 7 Nights Cruise in Guadeloupe And Its Islands

Sailing in Pointe-a-Pitre · 6 guests

"Monocoque" Sailboat's - 8 Days / 7 Nights Cruise in Guadeloupe And Its Islands

New

$10,196/day

28 GUESTS - OCEAN VOYAGER 53 CRUISING CATAMARAN

Sailing in Gustavia · 28 guests

28 GUESTS - OCEAN VOYAGER 53 CRUISING CATAMARAN

New

$582/hour

TORTOLA BVI - PRIVATE DAY SAILS ON 48' Privilege Catamaran Charter

Sailing in Wickhams Cay 1 · 20 guests

TORTOLA BVI - PRIVATE DAY SAILS ON 48' Privilege Catamaran Charter

New

$3,000/day

51' Neel Cruising Catamaran Rental in Le Marin, Martinique

Sailing in Rivière-Salée · 9 guests

51' Neel Cruising Catamaran Rental in Le Marin, Martinique

New

$1,581/day

The SeaPro Sun: Private 50-Person Charter w/ Open Bar & Snorkel

Sailing in El Cortecito · 50 guests

The SeaPro Sun: Private 50-Person Charter w/ Open Bar & Snorkel

New

$699/hour

Yacht Charter in Split Lagoon 46 Catamaran

Sailing in Florida · 13 guests

Yacht Charter in Split Lagoon 46 Catamaran

New

$802+/hour

Beach Monohulls Rental in Saboga, Panama

Sailing in Contadora · 5 guests

Beach Monohulls Rental in Saboga, Panama

New

$50/hour

15 Days14 Nights Cruise To The Islands Of The Wind - Antilles

Sailing in Pointe-a-Pitre · 6 guests

15 Days14 Nights Cruise To The Islands Of The Wind - Antilles

New

$37,554/day

Cartagena Sunset & Bay Tour on a Large 38 feet Luxury Boat (Private Tour)

Powerboats in Cartagena · 16 guests

Cartagena Sunset & Bay Tour on a Large 38 feet Luxury Boat (Private Tour)

5.0

Snoozed - Active 02 Aug 2026

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

New

Snoozed - Active 08 Jun 2026

Axe 1 Center Console Boat Rental in Montego Bay, Jamaica

Events in Montego Bay · 8 guests

Axe 1 Center Console Boat Rental in Montego Bay, Jamaica

New

Snoozed - Active 03 Sep 2026

COME AND SAIL ON THIS BEAUTIFUL ELAN MONOHULL BUILT FOR PERFORMANCE AND COMFORT

Sailing in Le Marin · 8 guests

COME AND SAIL ON THIS BEAUTIFUL ELAN MONOHULL BUILT FOR PERFORMANCE AND COMFORT

New

Snoozed - Active 12 Apr 2027

The Gallivanders Ultimate Sailing Adventure

Sailing in Nassau · 12 guests

The Gallivanders Ultimate Sailing Adventure

New

Snoozed - Active 03 Jan 2027

Enjoy Sailing in Fort Lauderdale Aboard the Sailing Vessel V1

Sailing in Fort Lauderdale · 4 guests

Enjoy Sailing in Fort Lauderdale Aboard the Sailing Vessel V1

New

Snoozed - Active 02 Aug 2026

Lagoon 420 Hybrid Eco Friendly Electric Catamaran

Sailing in Guna Yala Comarca · 4 guests

Lagoon 420 Hybrid Eco Friendly Electric Catamaran

New

Snoozed - Active 27 Mar 2027

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Sailing Reviews in Caribbean

CT
Catherine

Cartagena Sunset & Bay Tour on a Large 38 feet Luxury Boat (Private Tour)
Exceptional experience and exceptional service. Top quality on every aspect. Easy, clear, timely, effective communication. Beautiful and clean boat. Friendly, professional, helpful and caring staff. Amazing sunset and views. Highly recommended!
Terriun

Cartagena Sunset & Bay Tour on a Large 38 feet Luxury Boat (Private Tour)
We had a great experience on this boat. Nicolas was great accommodating and the staff was great with all of our needs during our trip. We highly recommend
MN
Michael

Cartagena Sunset & Bay Tour on a Large 38 feet Luxury Boat (Private Tour)
The staff was really friendly and the tour was perfect so see the impressive skyline of Cartagena. I had a lot if fun on the boat. It is worth the money.
DR
Doug

Cartagena Sunset & Bay Tour on a Large 38 feet Luxury Boat (Private Tour)
Great time on Nicholas's 401k boat! Highly recommend!

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