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All listings in Caribbean

Awesome sailboat rentals in the Caribbean.

4.8
(2,354 Reviews)

Page 18 of 19440 listings

Beneteau Oceanis 41 for sailing adventures in San Blas Islands
Sailing in Guna Yala Comarca · 3 guests

Beneteau Oceanis 41 for sailing adventures in San Blas Islands

New
$185/day
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
$467+/hour
Romantic Sunset Sailing in La Boquilla, Bolívar
Sailing in La Boquilla · 4 guests

Romantic Sunset Sailing in La Boquilla, Bolívar

New
$260/hour
Beneteau 50 Sailing Yacht Charter in San Blas Islands
Colón · 10 guests

Beneteau 50 Sailing Yacht Charter in San Blas Islands

New
$1,400/day
Jamaican Party Boat In Punta Cana Noahs Ark
Sailing in Bávaro · 50 guests

Jamaican Party Boat In Punta Cana Noahs Ark

New
$265/hour
Sailing Yacht Charter with amazing crew all inclusive
Sailing in Panama City · 6 guests

Sailing Yacht Charter with amazing crew all inclusive

New
$888/night
28 GUESTS - OCEAN VOYAGER 53 CRUISING CATAMARAN
Events in The Valley · 28 guests

28 GUESTS - OCEAN VOYAGER 53 CRUISING CATAMARAN

New
$701/hour
Bali Catspace 40' Catamaran in Ft Lauderdale for charter to Florida Keys
Sailing in Fort Lauderdale · 12 guests

Bali Catspace 40' Catamaran in Ft Lauderdale for charter to Florida Keys

New
$1,400/day
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
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
$1,168/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
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
28 GUESTS - OCEAN VOYAGER 53 CRUISING CATAMARAN
Sailing in Gustavia · 28 guests

28 GUESTS - OCEAN VOYAGER 53 CRUISING CATAMARAN

New
$584/hour
"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
$10,234/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
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
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
$1,586/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
$37,693/day
Private Tours~ Snorkeling at Palomino & Icacos Islands- Pursuit 28'
Tours in Fajardo · 6 guests

Private Tours~ Snorkeling at Palomino & Icacos Islands- Pursuit 28'

5.0
Superowner
Best of 2026
Snoozed - Active 23 May 2026
Luxury Sailing Catamaran for up to 12
Sailing in Cruz Bay · 12 guests

Luxury Sailing Catamaran for up to 12

5.0
Snoozed - Active 11 May 2026

Sailing Reviews in Caribbean

  1. JL

    Jessica

    Private Tours~ Snorkeling at Palomino & Icacos Islands- Pursuit 28'

    Jose was the best Captain! He took us to Icacos, Palomino, a ride by Palominito, and a ride by Islets Marina! Great food and drinks… Had a blast! Couldn’t have asked for a better experience!!!

  2. OZ

    Osmar

    Private Tours~ Snorkeling at Palomino & Icacos Islands- Pursuit 28'

    Great trip. Our party of 6 really enjoyed it. We asked for a food option and they made an incredible BBQ. The snorkel equipment was great and they were very attentive through the trip.

  3. Gavin

    Gavin

    Private Tours~ Snorkeling at Palomino & Icacos Islands- Pursuit 28'

    José was great! Kept the energy going, showed us a lot of great spots, kept us fed, and we had an outstanding time. Highly recommend.

  4. AM

    Andie

    Private Tours~ Snorkeling at Palomino & Icacos Islands- Pursuit 28'

    Captain Jose was an absolute blast and made my mom’s 60th birthday so special and memorable. From the moment we stepped on board, he brought great energy, made everyone feel comfortable, and truly made the day fun. When we arrived, the original boat we had booked was unfortunately having mechanical issues, which was a bit disappointing at first. However, the team handled it well and upgraded the experience by letting us use the Seabob for free—which ended up being a huge highlight of the day. We loved visiting Icacos Island—it was beautiful, relaxing, and the perfect spot to celebrate. Captain Jose knew exactly how to make the experience enjoyable and stress-free. We would absolutely recommend Captain Jose to anyone looking for an unforgettable day on the water. He truly went above and beyond to make the celebration special.

  5. SS

    Simon

    Luxury Sailing Catamaran for up to 12

    Unforgettable Post-Wedding Sail!! We spent a half-day with Aaron on the Catamaran Quest right after our wedding in St. Thomas, and it was easily one of the highlights of our entire trip. From the moment we stepped on board, Aaron made us feel incredibly special. He was super attentive and helpful, ensuring we had everything we needed to just relax and soak in the "just married" bliss. The food and drinks he served were fantastic—well-prepared and exactly what we needed for a day on the water. The boat itself is awesome and very well-equipped with everything you’d want for a comfortable excursion. We did encounter some minor technical issues with the engines during our trip, but Aaron handled it with total professionalism and didn't let it dampen the experience at all. If you are looking for a captain who truly cares about his guests' experience, book with Aaron. Thank you for making our celebration so memorable! PS: Aaron’s mango salsa is to die for - awesome stuff!!

  6. JF

    Jorge

    Private Tours~ Snorkeling at Palomino & Icacos Islands- Pursuit 28'

    Great experience with great hosts. Nice boat took us out to Palomino and Icacos, and the family had a blast. Great music, snacks, and beverages were on point. Overall, it exceeded my expectations. Will definitely book again with Jose and team.