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All listings in Caribbean

Awesome sailboat rentals in the Caribbean.

4.7
(2,366 Reviews)

Page 9 of 18432 listings

Private 3-Hour Sunset Catamaran Cruise to Media Luna Pool
Sailing in Dominican Republic · 45 guests

Private 3-Hour Sunset Catamaran Cruise to Media Luna Pool

New
$1,100/hour
Private 40ft Catamaran Charter in Miches, El Seibo: Snorkeling & Lunch
Sailing in Dominican Republic · 35 guests

Private 40ft Catamaran Charter in Miches, El Seibo: Snorkeling & Lunch

New
$1,050/hour
Private 80-Guest Sailing Catamaran Charter to Cayo Levantado
Sailing in El Centro · 80 guests

Private 80-Guest Sailing Catamaran Charter to Cayo Levantado

New
$500/hour
Puerto Plata Party Catamaran Jacuzzi Slide Barbecue and Bar
Sailing in Sosúa · 20 guests

Puerto Plata Party Catamaran Jacuzzi Slide Barbecue and Bar

New
$425/hour
Instant Book
Puerto Plata Private Sunset Catamaran Cruise with Open Bar and BBQ
Sailing in Sosúa · 10 guests

Puerto Plata Private Sunset Catamaran Cruise with Open Bar and BBQ

New
$260/hour
Instant Book
Private 47ft Power Catamaran to Saona Island – Full-Day All-Inclusive Experience
Sailing in Los Melones · 35 guests

Private 47ft Power Catamaran to Saona Island – Full-Day All-Inclusive Experience

New
$850/hour
Instant Book
MAXIMA Powerboat 38ft in Cartagena de Indias
Powerboats in Cartagena · 20 guests

MAXIMA Powerboat 38ft in Cartagena de Indias

4.0
$830/day
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
$1,395/day
51ft Beneteau Cyclades Crewed Sailing Charter in St. John, U.S. Virgin Islands
Sailing in St. John · 8 guests

51ft Beneteau Cyclades Crewed Sailing Charter in St. John, U.S. Virgin Islands

New
$1,990/day
🛥️🏝️ 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
Rosario Islands Private Cruise – 40ft Catamaran from Cartagena
Powerboats in Cartagena · 40 guests

Rosario Islands Private Cruise – 40ft Catamaran from Cartagena

New
$750/hour
Instant Book
Private 40ft Catamaran Charter to Rosario Islands, Cartagena
Sailing in Cartagena · 18 guests

Private 40ft Catamaran Charter to Rosario Islands, Cartagena

New
$500/hour
Instant Book
Sail St Maarten on 42ft Gibsea SunDowner Crusing Monohull
Caribbean · 10 guests

Sail St Maarten on 42ft Gibsea SunDowner Crusing Monohull

5.0
$1,200/day
Punta Cana 60' Private Luxury Power Catamaran to Catalina Island
Powerboats in Punta Cana · 65 guests

Punta Cana 60' Private Luxury Power Catamaran to Catalina Island

New
$530/hour
Instant Book
🟢🍾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
Montego Bay Escape – 47ft Voyage Catamaran Snorkel & Party Cruise
Sailing in Montego Bay · 30 guests

Montego Bay Escape – 47ft Voyage Catamaran Snorkel & Party Cruise

New
Superowner
$500/hour
Sail from Delray Beach to Lake Boca
Sailing in Delray Beach · 12 guests

Sail from Delray Beach to Lake Boca

1.0
Superowner
$125+/hour
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
Sailing live aboard  Charter in Montego Bay, Jamaica
Sailing in Montego Bay · 15 guests

Sailing live aboard Charter in Montego Bay, Jamaica

5.0
$950/day
Bachelorette Dancing Party In Luxury Cruise in Punta Cana, La Altagracia
Events in Bávaro · 200 guests

Bachelorette Dancing Party In Luxury Cruise in Punta Cana, La Altagracia

New
Superowner
Best of 2026
$17/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
Private 6-Hour Sailing Catamaran Charter in Punta Cana – Esmeralda
Sailing in Bávaro · 60 guests

Private 6-Hour Sailing Catamaran Charter in Punta Cana – Esmeralda

New
$265+/hour
Instant Book
Luxury 52 Catamaran With  AC - Price include 2 People
Sailing in Guna Yala Comarca · 8 guests

Luxury 52 Catamaran With AC - Price include 2 People

5.0
$3,000/day
42' Luxury Catamaran Sailboat
Sailing in Miami · 12 guests

42' Luxury Catamaran Sailboat

New
$300/hour

Sailing Reviews in Caribbean

  1. 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!

  2. DP

    Dawn

    Luxury 52 Catamaran With AC - Price include 2 People

    ⭐⭐⭐⭐⭐ An unforgettable experience in San Blas, Panama! The Italian-owned boat exceeded all expectations. The food was divine, reflecting true Italian finesse, and the service was impeccable. Every moment aboard was filled with warmth, comfort, and authentic hospitality. A must-try for anyone seeking a remarkable sailing adventure in paradise!

  3. CT

    Cassie

    Sail St Maarten on 42ft Gibsea SunDowner Crusing Monohull

    We had a great experience with Garth and Byron! They shared lots of fun information about the island and we had a great day of snorkeling and sailing. Would definitely recommend for a group of 6-8 versus jumping on a big boat with lots of people.

  4. Kurt

    Kurt

    Private Sail tour to Les Saintes with Skipper Sailing teacher

    Oliver is a great captain and knows how to create a wonderful and safe experience. I highly recommend you consider a sailing trip with Oliver.

  5. SY

    Sierra

    MAXIMA Powerboat 38ft in Cartagena de Indias

    The boat crew helped themselves to our beverages, held our itinerary up with their lunch, and didn’t communicate so we couldn’t go everywhere we wanted. They were fine, but I expected a little more from a luxury experience. The boat itself was very beautiful.

  6. JR

    Janell

    Sail St Maarten on 42ft Gibsea SunDowner Crusing Monohull

    Garth and Byron really made sure that we had a good time! I would definitely use them again when I come back to St Martin!