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All listings in Caribbean

Awesome sailboat rentals in the Caribbean.

4.8
(2,326 Reviews)

Page 1 of 19450 listings

🌴 St. Lucia Yacht Escape – Sail, Snorkel & Soak in Paradise
Sailing in Gros Islet · 12 guests

🌴 St. Lucia Yacht Escape – Sail, Snorkel & Soak in Paradise

5.0
$130/hour
Sail away in Montego Bay! 39ft Leopard Catamaran
Sailing in Montego Bay · 16 guests

Sail away in Montego Bay! 39ft Leopard Catamaran

5.0
Superowner
$600/hour
Private San Juan Bay Cruise 37' Sailboat
Sailing in San Juan · 6 guests

Private San Juan Bay Cruise 37' Sailboat

5.0
Superowner
Best of 2026
$195/hour
🏆BEST 2024🏆 Luxurious & elegant yacht designed for maximum comfort rent me!
Events in Bávaro · 80 guests

🏆BEST 2024🏆 Luxurious & elegant yacht designed for maximum comfort rent me!

4.3
Superowner
Best of 2026
$45/hour
Luxury 48' Leopard Catamaran in Cartagena
Sailing in Cartagena · 25 guests

Luxury 48' Leopard Catamaran in Cartagena

4.8
Superowner
Best of 2026
$200+/hour
46 feet luxury yacht in Montego Bay with unlimited cocktails and meals included
Powerboats in Montego Bay · 16 guests

46 feet luxury yacht in Montego Bay with unlimited cocktails and meals included

5.0
Superowner
Best of 2026
$599/hour
New addition! Lagoon 450 Catamaran
Sailing in George Town · 30 guests

New addition! Lagoon 450 Catamaran

5.0
$500/hour
Lagoon 450 Sailing Catamaran Charter in Saint Martin Community
Sailing in Anse Marcel · 20 guests

Lagoon 450 Sailing Catamaran Charter in Saint Martin Community

4.9
$1,887/day
Sailing Catamaran Grand Cayman for Sunrise, Sunset or Any Time Cruise
Sailing in West Bay · 20 guests

Sailing Catamaran Grand Cayman for Sunrise, Sunset or Any Time Cruise

5.0
$400/hour
Private Tours~ Snorkeling at Palomino & Icacos Islands- Pursuit 28'
Tours in Fajardo · 6 guests

Private Tours~ Snorkeling at Palomino & Icacos Islands- Pursuit 28'

5.0
Superowner
Best of 2026
$675/day
Yacht Adventure⭐️⭐️⭐️⭐️⭐️Fun Memories, Captain & Crew Included
Events in El Cortecito · 100 guests

Yacht Adventure⭐️⭐️⭐️⭐️⭐️Fun Memories, Captain & Crew Included

5.0
Superowner
Best of 2026
$15/hour
Memorable Punta Cana Boat Party Awaits! Inquire our Private Yacht Charter now!
Events in Punta Cana · 100 guests

Memorable Punta Cana Boat Party Awaits! Inquire our Private Yacht Charter now!

5.0
Superowner
Best of 2026
$15/hour
Private Charter Leopard 43 Catamaran in St Lucia
Sailing in Rodney Bay · 20 guests

Private Charter Leopard 43 Catamaran in St Lucia

5.0
$1,500/day
🏆5-Star Luxury Yacht: B-DAY PARTY & Crew TOTALLY PRIVATE 🎉
Events in Bávaro · 80 guests

🏆5-Star Luxury Yacht: B-DAY PARTY & Crew TOTALLY PRIVATE 🎉

5.0
Superowner
Best of 2026
$45/hour
The 30ft in Cruises at Barbados
Sailing in Welches · 12 guests

The 30ft in Cruises at Barbados

5.0
$180+/hour
Cabbage Key, Captiva Day Trip 1-6 people Captained
Powerboats in Cape Coral · 6 guests

Cabbage Key, Captiva Day Trip 1-6 people Captained

5.0
$100+/hour
Luxury Afloat In Antigua Onboard Jeanneau Sun Odyssey 519 Sailboat
Sailing in Jolly Harbour · 8 guests

Luxury Afloat In Antigua Onboard Jeanneau Sun Odyssey 519 Sailboat

5.0
$80/hour
Luxury Catamaran Lagoon 52' Capacity up to 40
Powerboats in Cartagena · 40 guests

Luxury Catamaran Lagoon 52' Capacity up to 40

5.0
Superowner
$200/hour
Catamaran in Saint George's
Sailing in Saint George's · 55 guests

Catamaran in Saint George's

4.9
$176+/hour
⛵️ Catamaran Party Boat 50' (49-Person)
Sailing in Miami Beach · 42 guests

⛵️ Catamaran Party Boat 50' (49-Person)

5.0
Superowner
$700+/hour
Sailing & Snorkeling Day Charter - Fajardo, Puerto Rico
Sailing in Fajardo · 6 guests

Sailing & Snorkeling Day Charter - Fajardo, Puerto Rico

5.0
$1,395/day
😎ADULT ONLY PARTY BOAT WITH UNLIMITED DRINKS,SNACKS, SAND-BAR, SNORKEL,MUSIC🥳
Events in Punta Cana · 150 guests

😎ADULT ONLY PARTY BOAT WITH UNLIMITED DRINKS,SNACKS, SAND-BAR, SNORKEL,MUSIC🥳

4.0
Superowner
Best of 2026
$45/hour
Explore Fort Lauderdale on 60ft Fountaine Pajot Yacht!
Sailing in Fort Lauderdale · 13 guests

Explore Fort Lauderdale on 60ft Fountaine Pajot Yacht!

5.0
Superowner
Best of 2026
$425+/hour
Sailing From Pompano Beach, FL
Sailing in Pompano Beach · 12 guests

Sailing From Pompano Beach, FL

4.5
Superowner
$125+/hour

Sailing Reviews in Caribbean

  1. AM

    Andie

    Private Tours~ Snorkeling at Palomino & Icacos Islands- Pursuit 28'

    Captain Jose was an absolute blast and made my mom’s 60th birthday so special and memorable. From the moment we stepped on board, he brought great energy, made everyone feel comfortable, and truly made the day fun. When we arrived, the original boat we had booked was unfortunately having mechanical issues, which was a bit disappointing at first. However, the team handled it well and upgraded the experience by letting us use the Seabob for free—which ended up being a huge highlight of the day. We loved visiting Icacos Island—it was beautiful, relaxing, and the perfect spot to celebrate. Captain Jose knew exactly how to make the experience enjoyable and stress-free. We would absolutely recommend Captain Jose to anyone looking for an unforgettable day on the water. He truly went above and beyond to make the celebration special.

  2. JD

    Jessica

    Sailing Catamaran Grand Cayman for Sunrise, Sunset or Any Time Cruise

    I cannot speak more highly of our sailing adventure with James and Nino! They were so accommodating, so much fun and took us to the most amazing spots for snorkeling. We even got to swim with stingrays. THE BEST EXPERIENCE!!!

  3. LW

    Lori

    Lagoon 450 Sailing Catamaran Charter in Saint Martin Community

    Fabulous trips around Saint Martin and over to Anguilla on 2 different trips. Our party of 8 enjoyed it immensely and were well taken care of. Do not hesitate to book as everything they promise will be there.

  4. RI

    Roman

    Luxury Catamaran Lagoon 52' Capacity up to 40

    ⭐️⭐️⭐️⭐️⭐️ We had an amazing day on the water—everything was perfect from start to finish. The crew was outstanding: friendly, professional, and always attentive to every detail, making sure we were comfortable and enjoying every moment. The sailing was smooth, the atmosphere on board was fantastic, and the entire experience exceeded our expectations. Without a doubt, a memorable day at sea. Highly recommended!

  5. MJ

    Mariah

    New addition! Lagoon 450 Catamaran

    Capt Dean and Jasper were nothing less than amazing. The boat itself was beautiful, and had all the amenities my group needed and more. They were accommodating in more than ways than one and which allowed us to have an amazing experience. I was comfortable, and knew I was in good hands with our boating adventures. I thank both of them over and over and will definitely be the only captain/boat I book with when I visit the Cayman Islands.

  6. JO

    James

    🌴 St. Lucia Yacht Escape – Sail, Snorkel & Soak in Paradise

    We had the best time with Capt. Nico and his crew! I would highly recommend booking this boat and crew. Everyone in our group thoroughly enjoyed the day. Snorkeling was amazing. Capt. Nico picked us up on time and got us back to the ship in plenty of time, we even had time to go to the open air market across the street from the port. Beverly provided great communication before our trip and everything went as arranged. When I come back to St. Lucia I will definitely book this trip again.