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All listings in Caribbean

Awesome sailboat rentals in the Caribbean.

4.8
(2,281 Reviews)

Page 7 of 19438 listings

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
Sailing Cruise Saint John
Sailing in Cruz Bay · 6 guests

Sailing Cruise Saint John

5.0
$197/hour
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
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
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
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
Full Day 50' Private Sailing Catamaran. Luxury, Beach/Snorkel. Departs Red Hook
Sailing in St. Thomas · 12 guests

Full Day 50' Private Sailing Catamaran. Luxury, Beach/Snorkel. Departs Red Hook

5.0
$2,395/day
Luxury Day Catamaran Charters ANTIGUA
Sailing in Saint John's · 65 guests

Luxury Day Catamaran Charters ANTIGUA

5.0
$1,000/hour
Luxury Private Catamaran Charter – All-Inclusive from St. Maarten
Caribbean · 16 guests

Luxury Private Catamaran Charter – All-Inclusive from St. Maarten

5.0
$2,095/day
Aicon 67 Fly  – Elite Luxury Yacht Experience
Events in Miami · 13 guests

Aicon 67 Fly – Elite Luxury Yacht Experience

New
$350/hour
Instant Book
3-Hours Puerto Plata Private Catamaran Cruise with BBQ Drinks and Snorkel
Powerboats in Sosúa · 15 guests

3-Hours Puerto Plata Private Catamaran Cruise with BBQ Drinks and Snorkel

New
$332/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
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 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
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
$922+/night
Imagine Sailing Catamaran Charter in Simpson Bay, Sint Maarten
Caribbean · 12 guests

Imagine Sailing Catamaran Charter in Simpson Bay, Sint Maarten

5.0
$1,500/day
2 Hour Sunset River Cruise for up to 6 people in Fort Lauderdale
Sailing in Fort Lauderdale · 6 guests

2 Hour Sunset River Cruise for up to 6 people in Fort Lauderdale

5.0
$150/hour
🥂EXCLUSIVE ISLAND CRUISE ENTERTAINMENT BAR MUSIC DANCE PARTY CAPTAIN CHARTER 🏝
Events in Bávaro · 100 guests

🥂EXCLUSIVE ISLAND CRUISE ENTERTAINMENT BAR MUSIC DANCE PARTY CAPTAIN CHARTER 🏝

New
Superowner
Best of 2026
$15/hour
Lagoon 42' Private Sailing Adventure in Florida with Captain Eric
Sailing in Deerfield Beach · 8 guests

Lagoon 42' Private Sailing Adventure in Florida with Captain Eric

5.0
$300/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
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
40 ft Jeanneau Sloop Charter in Fort Lauderdale
Sailing in Fort Lauderdale · 6 guests

40 ft Jeanneau Sloop Charter in Fort Lauderdale

5.0
$109+/hour
Limited Availability
🥂AMAZING PRIVATE YACHT🥂
Powerboats in La Romana · 50 guests

🥂AMAZING PRIVATE YACHT🥂

5.0
Superowner
Best of 2026
$50/hour

Sailing Reviews in Caribbean

  1. 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

  2. Andrea

    Andrea

    Luxury Sailing Catamaran Charter in Fajardo, Puerto Rico

    boat and crew were amazing ! We had a blast and they were very accommodating and friendly. Beautiful big boat! we had a great time and saw so many beautiful places. Food was good! Drinks were good! We will definitely be using them again! Thank you for wonderful moments !

  3. Caitlin

    Caitlin

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

    This was one of the best days of our lives! Christina and Jon were beyond accommodating. The drinks, the FOOD (get the lobster and mahi), the music, the snorkeling (saw so many beautiful fish and sea turtles!!) and the conversation were so enjoyable. These people know the islands so well and teach you a lot on top of giving you one of the best experiences of your life! Could not recommend it enough!!!!!

  4. KR

    Kelsey

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

    Jon and his team delivered the best experience of our St. John’s vacation. This is an island best seen by boat. Our kids are young (2,5,7). He customized an itinerary, snacks etc to the group. We went to one beautiful beach with turtles and a great snorkeling spot with fish. As our kids say, three thumbs up!

  5. LK

    Liz

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

    Jon and Christina were absolutely amazing! They made the experience so much fun and were very accommodating to everything we wanted to do, whether snorkeling, bringing us into to hang on the beach or whatever we wanted to experience. They also served the best food and drinks, it was the best part of our trip!

  6. ML

    Michael

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

    We have been on multiple day trips around the water during our stay on St. John. Our trip with Jon and Christina was by far the best experience. They actually asked us for input and what we would like to see and do. The lunch they served us was the best meal we have had here on St. John. Not only was it the best experience, it was also the best value. I highly recommend this duo for a great afternoon of sailing and snorkeling. We will be back.