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All listings in Caribbean

Awesome sailboat rentals in the Caribbean.

4.8
(2,311 Reviews)

Page 8 of 18427 listings

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
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
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
$117+/hour
Aicon 67 Fly  – Elite Luxury Yacht Experience
Events in Miami · 13 guests

Aicon 67 Fly – Elite Luxury Yacht Experience

New
$350/hour
Instant Book
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
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
Mambo 40ft Sail Catamaran
Caribbean · 20 guests

Mambo 40ft Sail Catamaran

5.0
$1,500/day
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
Puerto Plata Boat Budget-Friendly B-day Party Charter with Deals!
Powerboats in Sosúa · 80 guests

Puerto Plata Boat Budget-Friendly B-day Party Charter with Deals!

New
Superowner
Best of 2026
$50/hour
St. Kitts Coastline Cruise & Beach
Tours in Basseterre · 45 guests

St. Kitts Coastline Cruise & Beach

5.0
$147/hour
Custom Catamaran Trip in Punta Cana - Book With Us!
Powerboats in Punta Cana · 80 guests

Custom Catamaran Trip in Punta Cana - Book With Us!

New
Superowner
Best of 2026
$117+/hour
50ft Catamaran sail experience in Aruba. OPEN BAR AND Lunch included!!
Sailing in Oranjestad-West · 40 guests

50ft Catamaran sail experience in Aruba. OPEN BAR AND Lunch included!!

4.0
$1,120/hour
Private Sail tour to Les Saintes with Skipper Sailing teacher
Sailing in Saint Charles · 9 guests

Private Sail tour to Les Saintes with Skipper Sailing teacher

5.0
$1,383/day
Punta Cana - PRIVATE BOAT MAX BBQ
Sailing in Bávaro · 40 guests

Punta Cana - PRIVATE BOAT MAX BBQ

New
$575/hour
Leopard Power Catamaran 51ft - 2018 model from Saint Martin, Anse Marcel
Powerboats in Saint Martin · 12 guests

Leopard Power Catamaran 51ft - 2018 model from Saint Martin, Anse Marcel

5.0
$3,065/day
Punta Cana - PRIVATE MEDIUM GROUP (FRANK)
Sailing in Bávaro · 35 guests

Punta Cana - PRIVATE MEDIUM GROUP (FRANK)

New
$375/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
50ft Luxury Catamaran – Rose Island, Gilligan’s Island & Green Cay
Sailing in Nassau · 12 guests

50ft Luxury Catamaran – Rose Island, Gilligan’s Island & Green Cay

5.0
$1,375/hour
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
Puerto Plata Luxury Catamaran Charter with Snorkeling & Lunch
Powerboats in Sosúa · 70 guests

Puerto Plata Luxury Catamaran Charter with Snorkeling & Lunch

New
$242/hour
MAXIMA Powerboat 38ft in Cartagena de Indias
Powerboats in Cartagena · 20 guests

MAXIMA Powerboat 38ft in Cartagena de Indias

4.0
$830/day
Snorkeling And Party Boat For Private Groups
Powerboats in Uvero Alto · 80 guests

Snorkeling And Party Boat For Private Groups

5.0
$167/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
🛥️🏝️ Snorkeling Cruise Charter in Puerto Plata🛥️🏝️
Sailing in Barrio Las Yaguitas · 18 guests

🛥️🏝️ Snorkeling Cruise Charter in Puerto Plata🛥️🏝️

New
Superowner
Best of 2026
$75/hour

Sailing Reviews in Caribbean

  1. JP

    Jonathan

    Lagoon 42' Private Sailing Adventure in Florida with Captain Eric

    Amazing experience. Exceeded all expectations. I booked a trip for eight family members to celebrate a birthday while on vacation. Captain Eric took us on an afternoon tour of the Florida intercoastal. His boat was incredibly nice and spacious, and Eric was a great host - very friendly and accommodating to all our needs. We hope to book a sailing excursion with him next time we are in the area!

  2. SS

    Shaun

    40 ft 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. 🙌

  3. Kathy

    Kathy

    40 ft 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!

  4. 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!

  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. 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!