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All listings in Caribbean

Awesome sailboat rentals in the Caribbean.

4.7
(2,411 Reviews)

Page 8 of 20 • 460 listings

Catamaran Lose 50 Country House La Romana
Sailing in La Romana · 20 guests

Catamaran Lose 50 Country House La Romana

New
$2,088/day
40ft Jeanneau Sloop Charter in Fort Lauderdale
Sailing in Fort Lauderdale · 6 guests

40ft Jeanneau Sloop Charter in Fort Lauderdale

5.0
$109+/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
Catamaran Timaiao V, Crew included.  Saint Vincent and the Grenadines
Sailing in St. Andrew · 6 guests

Catamaran Timaiao V, Crew included. Saint Vincent and the Grenadines

5.0
$724+/night
🛥🥂VIP EXPERIENCE-Prívate Catamaran for bachelorette-birthday in Puerto Plata
Events in Barrio Las Yaguitas · 60 guests

🛥🥂VIP EXPERIENCE-Prívate Catamaran for bachelorette-birthday in Puerto Plata

1.0
$170/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
Cruising Catamaran Charter for Up to 65 People in St Maarten
Caribbean · 65 guests

Cruising Catamaran Charter for Up to 65 People in St Maarten

5.0
$1,800/day
Private Charters In Simpson Bay or Philipsburg
Caribbean · 30 guests

Private Charters In Simpson Bay or Philipsburg

5.0
$3,300/day
Power in Las Galeras
Sailing in Las Galeras · 10 guests

Power in Las Galeras

New
$1,580/day
30 foot Jupiter Center Console Rental in Fort Lauderdale, Florida
Powerboats in Deerfield Beach · 10 guests

30 foot Jupiter Center Console Rental in Fort Lauderdale, Florida

5.0
$200/hour
Rosario Islands Private Cruise – 40ft Catamaran from Cartagena
Powerboats in Cartagena · 15 guests

Rosario Islands Private Cruise – 40ft Catamaran from Cartagena

New
$4,999/day
Instant Book
Private boat planning room up to 100 people or more
Events in Bávaro · 300 guests

Private boat planning room up to 100 people or more

New
Superowner
Best of 2026
$20/hour
LUXURY PARTY YACHT IN BAVARO PERFECT FOR ANY OCCASION 😎
Events in Bávaro · 80 guests

LUXURY PARTY YACHT IN BAVARO PERFECT FOR ANY OCCASION 😎

New
Superowner
Best of 2026
$16/hour
Limited Availability
Mambo 40ft Sail Catamaran
Caribbean · 20 guests

Mambo 40ft Sail Catamaran

5.0
$1,500/day
Celebrate in Style with Luxury Yacht Charter in Punta Cana!
Powerboats in Punta Cana · 100 guests

Celebrate in Style with Luxury Yacht Charter in Punta Cana!

New
Superowner
Best of 2026
$17/hour
Enjoy Day Trips or Grenadines Cruises Onboard Our Luxury Catamaran
Sailing in Lance aux Epines · 6 guests

Enjoy Day Trips or Grenadines Cruises Onboard Our Luxury Catamaran

5.0
$800/day
EXCLUSIVE ISLAND CRUISE ENTERTAINMENT  MUSIC DANCE PARTY CAPTAIN CHARTER 🏝
Events in Bávaro · 100 guests

EXCLUSIVE ISLAND CRUISE ENTERTAINMENT MUSIC DANCE PARTY CAPTAIN CHARTER 🏝

New
Superowner
Best of 2026
$15/hour
Charter the Maxicat 65 Sailing Catamaran in Cartagena, Colombia
Sailing in Cartagena · 60 guests

Charter the Maxicat 65 Sailing Catamaran in Cartagena, Colombia

5.0
$3,500/day
Aicon 67 Fly  – Elite Luxury Yacht Experience
Events in Miami · 13 guests

Aicon 67 Fly – Elite Luxury Yacht Experience

New
$350/hour
Luxury Lagoon 50' Catamaran Charter In Grenada and The Grenadines
Sailing in Saint George's · 10 guests

Luxury Lagoon 50' Catamaran Charter In Grenada and The Grenadines

5.0
$200/hour
Punta Cana - PRIVATE MEDIUM GROUP (FRANK)
Sailing in Bávaro · 35 guests

Punta Cana - PRIVATE MEDIUM GROUP (FRANK)

New
$375/hour
Private Group Sail and Snorkel Montego Bay
Sailing in Montego Bay · 30 guests

Private Group Sail and Snorkel Montego Bay

5.0
$940/hour
Private 51ft Leopard Power Catamaran — Rosario Islands
Powerboats in Cartagena · 35 guests

Private 51ft Leopard Power Catamaran — Rosario Islands

New
$550/hour
Shared Catamaran to Cayo Icacos from Fajardo – $129 per Person, Lunch & Snorkel
Sailing in Fajardo · 44 guests

Shared Catamaran to Cayo Icacos from Fajardo – $129 per Person, Lunch & Snorkel

New
$129/day

Sailing Reviews in Caribbean

  1. SS

    Shaun

    40ft Jeanneau Sloop Charter in Fort Lauderdale

    This was our first time sailing and Captain Dan was amazing 🤩. He is very knowledgeable and accommodating. We sat up front on a couple of bean bags which was perfect and very comfortable. We will definitely do this again. Oh and we saw 👀dolphins 🐬 too. 🙌

  2. Kathy

    Kathy

    40ft Jeanneau Sloop Charter in Fort Lauderdale

    It was a great choice! Captain Dan welcomed us and prepared us so we would have a most enjoyable and safe trip! We toured beautiful areas, sailed along the coast and a great ocean adventure! We dropped anchor for a swim and lunch and had great conversation !! Thank you and we will be back!

  3. SH

    Susan

    Cruising Catamaran Charter for Up to 65 People in St Maarten

    Thank you so much Cathy and team! We had an incredible time on the Tango and would 100% do it again! The crew was fun and professional and ensured we had a wonderful snorkel and sail. Thank you again!! Definitely would recommend them and would book again!

  4. PA

    Peggy

    30 foot Jupiter Center Console Rental in Fort Lauderdale, Florida

    Our party of six adults and three children had the best time with Mike and his beautiful Jupiter 30. The boat was in immaculate order, had plenty of seating for all of us, and was safe for the kids to roam around on. A great sound system kept both kids and adults entertained. Mike truly is the best captain one can ask for. Quick to respond to our requests before the trip, and attentive, safe and positive during it. 10/10 from our whole party of nine

  5. James

    James

    Mambo 40ft Sail Catamaran

    Great experience and value. Snorkelling equipment for every member of our party! We stopped multiple times for snorkelling and to get food and the crew are amazing. They happily topped up drinks for us throughout the day and were full of energy. Highly recommend

  6. Amber

    Amber

    Enjoy Day Trips or Grenadines Cruises Onboard Our Luxury Catamaran

    We had a fantastic trip. My husband and I booked this trip for the Christmas holiday and Magali did a fantastic job of communicating with us leading up to the trip and even after we returned. We requested to see as much of Grenada as possible and an amazing itinerary was formulated for us. Our captain, Shaden, was the absolute best. He was knowledgeable, a great driver, and took into account our preferences. We even enjoyed some meals and played some games together. The boat is a little older but it is well kept and comfortable. We hope to come back for a longer trip soon!