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All listings in Caribbean

Awesome sailboat rentals in the Caribbean.

4.7
(2,259 Reviews)

Page 5 of 18417 listings

5-Star Vibes: All-Inclusive Captain & Crew - 65ft Ocean Explorer Catamaran
Events in Bávaro · 150 guests

5-Star Vibes: All-Inclusive Captain & Crew - 65ft Ocean Explorer Catamaran

4.0
Superowner
Best of 2026
$10/hour
41ft Metta Sailing Catamaran in Turks and Caicos Islands
Sailing in Leeward Settlement · 12 guests

41ft Metta Sailing Catamaran in Turks and Caicos Islands

5.0
$450/hour
Visit Culebra Island or Vieques Island / Private Tour
Tours in Fajardo · 6 guests

Visit Culebra Island or Vieques Island / Private Tour

5.0
Superowner
Best of 2026
$1,500/day
Private Full Day, Aboard SY Mazu - Luxury Gemini Catamaran w/Holiday Pricing
Sailing in St. Thomas · 12 guests

Private Full Day, Aboard SY Mazu - Luxury Gemini Catamaran w/Holiday Pricing

5.0
$1,550/day
Luxury Catamaran Trips in St Maarten and Surrounding Islands
Caribbean · 22 guests

Luxury Catamaran Trips in St Maarten and Surrounding Islands

5.0
$475/hour
44' Wellington Sailing Yacht In Antigua
Sailing in Jolly Harbour · 6 guests

44' Wellington Sailing Yacht In Antigua

5.0
$100/hour
ALL INCLUSIVE luxury day and overnight charter on the sailing catamaran Amura
Sailing in Nassau · 40 guests

ALL INCLUSIVE luxury day and overnight charter on the sailing catamaran Amura

5.0
$960/hour
YOUR DREAM ALL-INCLUSIVE CATAMARAN CHARTER PARTY 🎉
Events in Bávaro · 120 guests

YOUR DREAM ALL-INCLUSIVE CATAMARAN CHARTER PARTY 🎉

5.0
Superowner
Best of 2026
$117/hour
33ft The Key West's Most Versatile Sailboat! (With Captain Only)
Sailing in Key West · 12 guests

33ft The Key West's Most Versatile Sailboat! (With Captain Only)

4.6
$199+/hour
Curacao Private Morning Tour All Inclusive
Sailing in Jan Thiel · 6 guests

Curacao Private Morning Tour All Inclusive

5.0
$250/hour
Private Boat Rental Turks & Caicos
Powerboats in Long Bay Hills · 8 guests

Private Boat Rental Turks & Caicos

5.0
$200/hour
Half Day 50' Private Sailing Catamaran. Luxury, Beach/Snorkel. Departs Red Hook
Sailing in St. Thomas · 12 guests

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

4.9
$390/hour
🎉 Miches All Stars Cruise All Inclusive Luxury Yacht
Powerboats in Dominican Republic · 150 guests

🎉 Miches All Stars Cruise All Inclusive Luxury Yacht

5.0
Superowner
Best of 2026
$17/hour
Punta Cana - PRIVATE SMALL GROUP (CAT PAUSE)
Sailing in Bávaro · 15 guests

Punta Cana - PRIVATE SMALL GROUP (CAT PAUSE)

5.0
$250/hour
Sailing Hobie Cat Rental in Noord, Aruba
Sailing in Oranjestad-West · 4 guests

Sailing Hobie Cat Rental in Noord, Aruba

4.4
$89/hour
ENJOY UNLIMITED OPEN BAR TOUR 🏝️ PRIVATE CHARTER😎☀️
Events in Uvero Alto · 70 guests

ENJOY UNLIMITED OPEN BAR TOUR 🏝️ PRIVATE CHARTER😎☀️

3.7
Superowner
Best of 2026
$17/hour
Sunset Cruise in San Juan Puerto Rico
Sailing in San Juan · 6 guests

Sunset Cruise in San Juan Puerto Rico

5.0
Superowner
$353/hour
Montego Bay Private Champagne Sunset Catamaran Cruise
Powerboats in Montego Bay · 10 guests

Montego Bay Private Champagne Sunset Catamaran Cruise

New
$1,896/hour
Negril Private Catamaran Cruise with Snorkeling & Drinks
Sailing in West End · 120 guests

Negril Private Catamaran Cruise with Snorkeling & Drinks

New
$509/hour
Lagoon 400 18 People Cruising Catamaran In Cartagena, Colombia
Sailing in Cartagena · 18 guests

Lagoon 400 18 People Cruising Catamaran In Cartagena, Colombia

5.0
$1,700/day
Get ready for the ultimate cruise in Punta Cana
Events in Macao · 150 guests

Get ready for the ultimate cruise in Punta Cana

New
Superowner
Best of 2026
$17/hour
Curacao Private Sunset Tour Deluxe
Sailing in Santa Barbara Plantation · 6 guests

Curacao Private Sunset Tour Deluxe

5.0
$250/hour
!!Best 2025 Winner !! Power Catamaran in La Romana, Dominican Republic
Events in La Romana · 100 guests

!!Best 2025 Winner !! Power Catamaran in La Romana, Dominican Republic

5.0
Superowner
Best of 2026
$60/hour
Exclusive Day Sail on a Private Beneteau Oceanis 440 Sailboat
Sailing in Gros Islet · 10 guests

Exclusive Day Sail on a Private Beneteau Oceanis 440 Sailboat

5.0
$569/day

Sailing Reviews in Caribbean

  1. RM

    Richard

    ALL INCLUSIVE luxury day and overnight charter on the sailing catamaran Amura

    The Amura was the highlight of our time in the Bahamas! The communication was clear, and time at sea was fantastic. The boat had all the toys that our family could want. Captain Dan and crew make for a really enjoyable day. Also the food was incredible, come hungry!

  2. QW

    Quentin

    Exclusive Day Sail on a Private Beneteau Oceanis 440 Sailboat

    Great Captain you’ll be in trusted hands

  3. TW

    Terry

    41ft Metta Sailing Catamaran in Turks and Caicos Islands

    A perfect day on the Metta. After messaging about our grandkids interests, the captain took us to the boat wreck to snorkel and then to a great coral reef! Snacks, drinks and gear were provided and they were very helpful. Last, we swam and played on the most beautiful beach and the kids saw iguanas! Great hosts! We will book the Metta again!

  4. KH

    Kanisha

    41ft Metta Sailing Catamaran in Turks and Caicos Islands

    We had an amazing time with our group of 8 adults and 3 kids under 5. We had a totally customized itinerary and the crew is so incredibly helpful and welcoming. We had an amazing time on a half day charter and would definitely do a full day with this crew any time. The highlight of our trip was JoJo the dolphin following us during the whole charter! We got to snorkel with him and the kids were so happy to see him following alongside the boat the whole way!

  5. DL

    Dmitriy

    Visit Culebra Island or Vieques Island / Private Tour

    Highly recommend. We booked a day trip with Jose to Culebra Island (Flamenco beach) and really enjoyed the amazing day. The captain and the mate made our day exciting and unforgettable. There are a lot of beach toys, chairs, snorkeling gears, drinks and snacks on the boat, so you don't need to care about it. For extras you may get a bbq and/or a Seabob, which is cool underwater scooter. Will definitely book again.

  6. Lisa

    Lisa

    Private Full Day, Aboard SY Mazu - Luxury Gemini Catamaran w/Holiday Pricing

    We were a group of 13 and rented two catamaran’s for the afternoon. Captain JW was the captain for the boat I was on and he was terrific- took us to Scott beach on St. John for snorkeling and swimming. It was very pretty and he was very attentive in providing drinks and snorkeling equipment and good music. We sailed in tandem with the other catamaran that had the rest of our group on it and also went to a beautiful private resort called Lovango for lunch. Felt like a little taste of Europe in the US Virgin Islands. Only complaint was I wish we had even more time at sea but we had to get back on our cruise ship!