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All listings in Caribbean

Awesome sailboat rentals in the Caribbean.

4.8
(2,319 Reviews)

Page 7 of 19434 listings

60' Sailing Party Catamaran in Miami Florida
Sailing in Miami Beach · 49 guests

60' Sailing Party Catamaran in Miami Florida

4.6
$1,300/hour
AMAR IS THE WAY TO ENJOY
Events in Miami · 13 guests

AMAR IS THE WAY TO ENJOY

5.0
Superowner
$400+/hour
Catamaran Lose 50 Country House La Romana
Sailing in La Romana · 20 guests

Catamaran Lose 50 Country House La Romana

New
$2,088/day
Awesome and Spacious Sea Ray 55’ 2009 Motor Yacht Rental in Fajardo, Puerto Rico
Events in Fajardo · 12 guests

Awesome and Spacious Sea Ray 55’ 2009 Motor Yacht Rental in Fajardo, Puerto Rico

5.0
$800/hour
Ultimate Day Sailing Charter Onboard 40' Baba Sailboat in St. Thomas
Sailing in St. Thomas · 6 guests

Ultimate Day Sailing Charter Onboard 40' Baba Sailboat in St. Thomas

5.0
$220/hour
Isla Saona Private Yacht – Luxury Full-Day Tour
Powerboats in Bávaro · 20 guests

Isla Saona Private Yacht – Luxury Full-Day Tour

1.0
$1,820/day
60 Person Catamaran, Pet Friendly - Reserve Your Day On The Water With Us!
Powerboats in Bávaro · 200 guests

60 Person Catamaran, Pet Friendly - Reserve Your Day On The Water With Us!

New
Superowner
Best of 2026
$16/hour
Luxury Sailing Catamaran Charter in Fajardo, Puerto Rico
Sailing in Fajardo · 19 guests

Luxury Sailing Catamaran Charter in Fajardo, Puerto Rico

5.0
$450/hour
Sailing Charters On 37' Hunter Legend Cruising Monohull In Virgin Islands
Sailing in Charlotte Amalie West · 6 guests

Sailing Charters On 37' Hunter Legend Cruising Monohull In Virgin Islands

5.0
$210/hour
All-inclusive Luxury Private Charter - Power Cat - St Martin/Anguilla/St Barths
Caribbean · 12 guests

All-inclusive Luxury Private Charter - Power Cat - St Martin/Anguilla/St Barths

5.0
$2,298+/day
Lagoon 38 Catamaran trip in St Martin with skipper, departure from Orient bay
Sailing in Saint Martin · 12 guests

Lagoon 38 Catamaran trip in St Martin with skipper, departure from Orient bay

4.9
$1,143/day
Be Happy 40ft - Private Catamaran Charter - Discover the beautiful St Maarten
Caribbean · 12 guests

Be Happy 40ft - Private Catamaran Charter - Discover the beautiful St Maarten

5.0
$1,850/day
Sailing Cruise Saint John
Sailing in Cruz Bay · 6 guests

Sailing Cruise Saint John

5.0
$197/hour
45' Lagoon Sailing Catamaran in St. Thomas, U.S. Virgin Islands
Sailing in St. Thomas · 12 guests

45' Lagoon Sailing Catamaran in St. Thomas, U.S. Virgin Islands

5.0
$2,000/day
Lagoon 380 S2 S/V Timaiao, Chef included.  Saint Vincent and the Grenadines
Sailing in St. George · 6 guests

Lagoon 380 S2 S/V Timaiao, Chef included. Saint Vincent and the Grenadines

5.0
$924+/night
Luxury Day Catamaran Charters ANTIGUA
Sailing in Saint John's · 65 guests

Luxury Day Catamaran Charters ANTIGUA

5.0
$1,000/hour
The Best Day Sail in St. Maarten
Caribbean · 30 guests

The Best Day Sail in St. Maarten

5.0
$129/day
21ft Sun Tracker 20 Party Barge {Catch a Vibe}
Powerboats in Fort Lauderdale · 6 guests

21ft Sun Tracker 20 Party Barge {Catch a Vibe}

5.0
$100/hour
SPRING BREAK TIME🛥🔥 VIP Luxury Catamaran Party Sailing-Swimming in Punta Cana
Events in Bávaro · 150 guests

SPRING BREAK TIME🛥🔥 VIP Luxury Catamaran Party Sailing-Swimming in Punta Cana

3.8
$167/hour
S/Y Timshel Day and Term Charters, Grenada and Grenadines
Sailing in Saint George's · 6 guests

S/Y Timshel Day and Term Charters, Grenada and Grenadines

5.0
$660/day
VIP Power cruise - Your adventure platform waiting to whisk you away!
Events in Bávaro · 100 guests

VIP Power cruise - Your adventure platform waiting to whisk you away!

New
Superowner
Best of 2026
$15/hour
All inclusive sailing charters, half day full day fishing week long sunset sail
Sailing in Charlotte Amalie · 12 guests

All inclusive sailing charters, half day full day fishing week long sunset sail

5.0
$250/hour
Instant Book
COME AND ENJOY THE C'YA WITH US AND FAMILY
Events in Miami · 13 guests

COME AND ENJOY THE C'YA WITH US AND FAMILY

New
Superowner
$365+/hour
All Inclusive 40' Catamaran Sailing Experience - Old San Juan
Sailing in San Juan · 6 guests

All Inclusive 40' Catamaran Sailing Experience - Old San Juan

3.0
$725/hour

Sailing Reviews in Caribbean

  1. SF

    Steven

    S/Y Timshel Day and Term Charters, Grenada and Grenadines

    We had a great, relaxing day on our private charter for 2. Lunch was delicious and the crew was awesome! The owner always replied to our inquiries promptly during the booking phase. Would recommend to anyone looking for a perfect day on the water.

  2. JB

    Julia

    45' Lagoon Sailing Catamaran in St. Thomas, U.S. Virgin Islands

    Carrie is a great host, very responsive and easy to communicate with. We had a great time, this boat was very spacious and comfortable for our group of 11. We even got to swim with some turtles during our trip!

  3. JB

    John

    Lagoon 38 Catamaran trip in St Martin with skipper, departure from Orient bay

    Loved our two family excursion around St. Martin! Kids loved the big floating mat. Adults liked being on the ocean and snorkeling creole rock

  4. CW

    Catherine

    45' Lagoon Sailing Catamaran in St. Thomas, U.S. Virgin Islands

    Carrie was fantastic to work with when booking for our group. There were a lot of questions and some adjustments, and she was so kind a patient while answering everything! She even gave us a heads up the day of that there were storms coming so they might've not seen the sunset, and they were able to reschedule for the next day. Nothing but great things to say for the whole experience!

  5. Dana

    Dana

    Luxury Sailing Catamaran Charter in Fajardo, Puerto Rico

    Gabriela and her team are incredible! I’m happy to share that our experience was absolutely phenomenal from start to finish. East Island Excursions was incredibly professional and accommodating throughout the entire planning process. Communication was seamless, check-in was a breeze, and everything ran so smoothly on the day of our excursion. The boat itself was stunning and made the perfect backdrop for my sister’s bachelorette party—truly unforgettable. Most of all, the crew was exceptional. They were warm, welcoming, and attentive to every detail, making us feel so well taken care of. They genuinely went above and beyond to make the day feel special, and it showed in every interaction. We couldn’t have asked for a better experience and would absolutely recommend both Getmyboat and East Island Excursions to anyone looking for a memorable, stress-free adventure on the water. Thank you again for such a wonderful experience! Warmly, Dana

  6. RE

    Renee

    Lagoon 38 Catamaran trip in St Martin with skipper, departure from Orient bay

    Great day on the ocean! We spent the day snorkeling at lle Tintamarre; swam with the turtles, explored beach and used beach toys, then sailed to Creole Rock and snorkeled -saw lots of fish and a skate…and some jellyfish (not stinging). Then we sailed to pinel island for a late lunch and beach time. Overall wonderful day!! Would do again. Service was great and extra shoutout for getting grandma in and out of the boat!