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All listings in Caribbean

Awesome sailboat rentals in the Caribbean.

4.8
(2,357 Reviews)

Page 8 of 19440 listings

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
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
St. Kitts Coastline Cruise & Beach
Tours in Basseterre · 45 guests

St. Kitts Coastline Cruise & Beach

5.0
$147/hour
🟢🍾Ocean Escape: Snorkel, Sip & Celebrate with Open Bar & Music☀️
Powerboats in Punta Cana · 500 guests

🟢🍾Ocean Escape: Snorkel, Sip & Celebrate with Open Bar & Music☀️

New
Superowner
Best of 2026
$15/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
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
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
$1,407/day
44 Luxury Catamaran BIG BEN
Sailing in Leeward Settlement · 18 guests

44 Luxury Catamaran BIG BEN

New
$875+/hour
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
48 Ft Catamaran sailing on the Biscayne Bay . Party, Sound healing, Wingfoil
Sailing in Miami · 13 guests

48 Ft Catamaran sailing on the Biscayne Bay . Party, Sound healing, Wingfoil

5.0
$187+/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
Captained 80' Sailing Schooner Charter In Key West, Florida
Sailing in Key West · 32 guests

Captained 80' Sailing Schooner Charter In Key West, Florida

5.0
$475+/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
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
St. Martin Private Boat Tour with Lagoon 450 Cruising Catamaran
Sailing in Saint Martin · 20 guests

St. Martin Private Boat Tour with Lagoon 450 Cruising Catamaran

New
$1,877/day
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
🛥️🏝️ SAIL IN PUNTA CANA PRIVATE GROUPS 🛥️🏝️
Tours in Dominican Republic · 40 guests

🛥️🏝️ SAIL IN PUNTA CANA PRIVATE GROUPS 🛥️🏝️

New
Superowner
Best of 2026
$75/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
$3,120/day
Bahia de las Aguilas- Private Catamaran Cruise
Events in Dominican Republic · 70 guests

Bahia de las Aguilas- Private Catamaran Cruise

New
$500/hour
Private Charters In Simpson Bay or Philipsburg
Caribbean · 30 guests

Private Charters In Simpson Bay or Philipsburg

5.0
$3,300/day

Sailing Reviews in Caribbean

  1. 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!

  2. 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

  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. MW

    MAESHEN

    Private Sail tour to Les Saintes with Skipper Sailing teacher

    Une journée de Rêve à ne pas manquer! Le voilier porte bien son nom!!! La croisière était super! On a vraiment aimé voir la Guadeloupe depuis la mer. Avec possibilité de prendre la barre et d'aider avec les voiles. Nous avons déjà fait du voilier, mais jamais participer, donc c'était une bonne expérience. Skipper m très sympa et intéressant et nous avons appris beaucoup sur la Guadeloupe et le voilier. Apéro et repas aussi très bon😊. Vous ne regretterez pas! Je recommande! Vraiment belle journée!

  5. Michael

    Michael

    48 Ft Catamaran sailing on the Biscayne Bay . Party, Sound healing, Wingfoil

    My family had a wonderful day on The Bubble! Catherine and Serge responded quickly to our inquiries and were very accommodating of a request to change the time. They made us feel at home on the boat and the boat was great. They have a table outside and inside with seating, and a large area in the front to lounge. There have yoga mats and blankets we used and a speaker you can connect to. We were able to put our food in a fridge and a cooler. They provided water bottles. We enjoyed a fun ride in their dingy to go see the stilt houses in the bay as well. If you’re able to go on The Bubble at sunset you may be treated as we were to a gorgeous sunset over the water in addition to the great view of Miami lit up. Our captain Doug was great-super nice and professional and interesting to speak to him about the places he has lived all over the world. I highly recommend The Bubble!

  6. AD

    Alison

    48 Ft Catamaran sailing on the Biscayne Bay . Party, Sound healing, Wingfoil

    We had such an amazing time on the Bubble for my bachelorette party! The boat is huge and was very stable on the bay - no one got sea sick! We were able to sail the whole time except leaving the dock. Captain Serge made sure we had a great time and also made sure we were all super safe onboard. The main bathroom is very large for a boat and clean. We also loved hanging out on the floating mat in the water! I highly recommend and would love to sail on the Bubble again!