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All listings in Caribbean

Awesome sailboat rentals in the Caribbean.

4.7
(2,379 Reviews)

Page 19 of 19439 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 Oct 2026
All Inclusive 67' Fountaine Pajot Catamaran for Day and Overnight Charter
Sailing in Nassau · 24 guests

All Inclusive 67' Fountaine Pajot Catamaran for Day and Overnight Charter

5.0
Snoozed - Active 02 Nov 2026
52' Catamaran - Sunset Cruise Private Charter at Simpson Bay
Caribbean · 32 guests

52' Catamaran - Sunset Cruise Private Charter at Simpson Bay

New
Snoozed - Active 03 Mar 2027
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
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 02 Oct 2026

Sailing Reviews in Caribbean

  1. AF

    Allison

    All Inclusive 67' Fountaine Pajot Catamaran for Day and Overnight Charter

    What a day! That’s the best way I can describe this incredible experience. True Story is a true gem. Our crew, Steven our captain and Cecilia and Bianca made this a trip to remember. From the moment we boarded to the moment we left. We booked this trip for my mom’s 80th birthday. We had ages 21-80 and everyone fully enjoyed. From relaxing in the sun, to snorkeling, jet skiing, paddle boarding, walking on private beaches, and we even had a few try the E-Foil. It was constant fun! And I can’t say enough about the food. Beautiful, healthy and super yummy. We did not leave hungry. This was truly an experience of a lifetime and again, it would not have been the same without this incredible crew. We hope to be back to the Bahamas and we would 100% book this again. Thank you from the bottom of our hearts, True Story crew!

  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. 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!

  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. SH

    Sheri

    All Inclusive 67' Fountaine Pajot Catamaran for Day and Overnight Charter

    This boat is beautiful! The crew was attentive to our wants and needs! The food was fabulous! Would recommend 10 out of 10 !

  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!!