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All listings in Caribbean

Awesome sailboat rentals in the Caribbean.

4.7
(2,382 Reviews)

Page 19 of 19 • 442 listings

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
$36,863/day
🌴 St. Lucia Yacht Escape – Sail, Snorkel & Soak in Paradise
Sailing in Gros Islet · 12 guests

🌴 St. Lucia Yacht Escape – Sail, Snorkel & Soak in Paradise

5.0
Snoozed - Active 02 Dec 2026
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. Kathy

    Kathy

    🌴 St. Lucia Yacht Escape – Sail, Snorkel & Soak in Paradise

    What a wonderful time we had on the Karen P sailboat! Captain Nico went over our intinerary and was flexible and accomodating with our requests of sailing, docking, fishing, eating! The first mates Marlin and Grayson were always willing to please! We had 11 adults on board, sailed down to Soufriere to see the Pitons and back, with snacks and drinks, and were able to see the sun setting on our way home. It was a wonderful experience and we will be looking to hire the same crew in the future. Thank you Captian Nico!

  3. JO

    James

    🌴 St. Lucia Yacht Escape – Sail, Snorkel & Soak in Paradise

    We had the best time with Capt. Nico and his crew! I would highly recommend booking this boat and crew. Everyone in our group thoroughly enjoyed the day. Snorkeling was amazing. Capt. Nico picked us up on time and got us back to the ship in plenty of time, we even had time to go to the open air market across the street from the port. Beverly provided great communication before our trip and everything went as arranged. When I come back to St. Lucia I will definitely book this trip again.

  4. ek

    elizabeth

    🌴 St. Lucia Yacht Escape – Sail, Snorkel & Soak in Paradise

    Captain Nico and his crew did a great job providing our family of 5 a very fun day! The scenery was beautiful! The boat was comfortable and accommodating. We had fun snorkeling and they prepared a delicious lunch for us! We booked them during our port day on our cruise. Highly recommend!

  5. BR

    Brandi

    🌴 St. Lucia Yacht Escape – Sail, Snorkel & Soak in Paradise

    What a great trip! They met us at the port entrance and walked us to the sailboat. The crew was amazing, interactive and helped us have a great day! We rode to see the Pitons, stopped for swim and snorkeling, and enjoyed a yummy fresh cooked lunch on the way back to port. We listened to music and the Pitons beer and rum punch was flowing!

  6. Ricky

    Ricky

    🌴 St. Lucia Yacht Escape – Sail, Snorkel & Soak in Paradise

    This was an amazing experience. Communication from beginning to end was excellent. The captain and his crew went above and beyond for everyone involved. I cant recommend this highly enough. Ill be doing a YouTube video review of the whole experience soon. Highly satisfied customers.