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All listings in Caribbean

Awesome sailboat rentals in the Caribbean.

4.8
(2,282 Reviews)

Page 19 of 19440 listings

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
Snoozed - Active 02 Aug 2026
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
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
Punta Cana: Tasting the Tides - Rum, Sail and Swim | 4 hrs to full day options
Sailing in Bávaro · 12 guests

Punta Cana: Tasting the Tides - Rum, Sail and Swim | 4 hrs to full day options

New
Snoozed - Active 03 Jul 2026

Sailing Reviews in Caribbean

  1. 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

  2. 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.

  3. 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!

  4. KM

    Karrah

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

    Our trip was amazing, Jose and Suri were great. Beautiful locations, snacks, drinks, equipment. They even took photos and sent them to us. They were a great team and made it an amazing day for us. Would definitely book with them again!

  5. DE

    Daniel

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

    Loved black octopus for your sail. Was top notch service all the way around. Our most magical experience so far in San Juan.

  6. AL

    Amy

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

    Great experience for our family. We had a fantastic day, saw a dolphin, sea turtles and stingrays. We would highly recommend!!