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All listings in Caribbean

Awesome sailboat rentals in the Caribbean.

4.7
(2,413 Reviews)

Page 1 of 20 • 461 listings

Private San Juan Sailing | El Morro, Sunset, Charcuterie & Signature Cocktails
Sailing in San Juan · 6 guests

Private San Juan Sailing | El Morro, Sunset, Charcuterie & Signature Cocktails

5.0
Superowner
Best of 2026
$195/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
Limited Availability
Sailing Catamaran Grand Cayman Sunset, Stingray City, Starfish Point & Snorkel
Sailing in West Bay · 20 guests

Sailing Catamaran Grand Cayman Sunset, Stingray City, Starfish Point & Snorkel

5.0
$400/hour
Lagoon 450F Catamaran
Sailing in George Town · 30 guests

Lagoon 450F Catamaran

5.0
$500/hour
Limited Availability
Luxury 48' Leopard Catamaran in Cartagena
Sailing in Cartagena · 25 guests

Luxury 48' Leopard Catamaran in Cartagena

4.8
Superowner
Best of 2026
$213+/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
Open bar 🍹 & food 🍱 Sand-Bar Punta Cana Snorkeling Entertainment Booze cruise
Events in Bávaro · 300 guests

Open bar 🍹 & food 🍱 Sand-Bar Punta Cana Snorkeling Entertainment Booze cruise

4.3
Superowner
Best of 2026
$15/hour
Captained 42' Sailing Catamaran with 3 cabins and all the toys
Sailing in Key West · 6 guests

Captained 42' Sailing Catamaran with 3 cabins and all the toys

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

Lagoon 450 Sailing Catamaran Charter in Saint Martin Community

5.0
$1,796/day
23’ Bayliner Beautiful Boat In Miami
Sailing in Miami · 9 guests

23’ Bayliner Beautiful Boat In Miami

4.9
$90/hour
Available in Puerto Plata  Private Yacht Experience: Beautiful Views book now
Powerboats in Puerto Plata · 100 guests

Available in Puerto Plata Private Yacht Experience: Beautiful Views book now

5.0
Superowner
Best of 2026
$50/hour
Yacht Adventure⭐️⭐️⭐️⭐️⭐️Fun Memories, Captain & Crew Included
Events in El Cortecito · 100 guests

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

4.6
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
Lobster 🦞🍹cocktail Private Boat Experience: Beautiful Views, Captain Included
Events in Punta Cana · 50 guests

Lobster 🦞🍹cocktail Private Boat Experience: Beautiful Views, Captain Included

5.0
Superowner
Best of 2026
$15/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
Catamaran in Saint George's
Sailing in Saint George's · 55 guests

Catamaran in Saint George's

4.9
$175+/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
Limited Availability
Sailing & Snorkeling Day Charter - Fajardo, Puerto Rico
Sailing in Fajardo · 6 guests

Sailing & Snorkeling Day Charter - Fajardo, Puerto Rico

5.0
$1,395/day
The 30ft in Cruises at Barbados
Sailing in Welches · 12 guests

The 30ft in Cruises at Barbados

5.0
$180+/hour
🥳Dreams Birthday Party 5-Star Luxury Yacht - Totally Private🥳
Events in Uvero Alto · 150 guests

🥳Dreams Birthday Party 5-Star Luxury Yacht - Totally Private🥳

4.7
Superowner
Best of 2026
$15/hour
Enjoy cruising the Montego Bay coastline  In a 46  feet Searay yacht
Events in Montego Bay · 16 guests

Enjoy cruising the Montego Bay coastline In a 46 feet Searay yacht

4.9
Superowner
Best of 2026
$599/hour
⛵️ Catamaran Party Boat 50' (49-Person)
Sailing in Miami Beach · 42 guests

⛵️ Catamaran Party Boat 50' (49-Person)

5.0
Superowner
$700+/hour
Ultimate Catamaran Party Boat | Up to 49 Passengers!
Events in Miami · 49 guests

Ultimate Catamaran Party Boat | Up to 49 Passengers!

4.9
Superowner
$700+/hour
Limited Availability
Charter the 36' Fountaine Pajot Tobago Cruising Catamaran in Cartagena, Colombia
Sailing in Cartagena · 16 guests

Charter the 36' Fountaine Pajot Tobago Cruising Catamaran in Cartagena, Colombia

4.8
Superowner
$870/day

Sailing Reviews in Caribbean

  1. SL

    Sheri

    Private San Juan Sailing | El Morro, Sunset, Charcuterie & Signature Cocktails

    Luis and Andrea were so sweet and knowledgeable. Not only did we feel safe on the boat but we also got a lot of historical info. They were also fun and friendly! The sangria was delish!! We had bad weather so we couldn’t get in the water but it was still a relaxing and fun adventure!

  2. AN

    Ann

    Private Charter Leopard 43 Catamaran in St Lucia

    We were a group of 18 persons and we all had a great time. There was plenty of drinks from non alcoholic to alcoholic. We included a stop at the mud baths and waterfall. The staff were accommodating and friendly.

  3. BS

    Bria

    Lagoon 450 Sailing Catamaran Charter in Saint Martin Community

    Book with captain Sup!! Him and Zoey were amazing to us! It was my birthday and there were 14 of us and all needs were accommodated. They were very sweet and kind to all of us and took us to really cool beaches!

  4. MG

    Misty

    Sailing & Snorkeling Day Charter - Fajardo, Puerto Rico

    Captain Ivan and mate Monica, by far exceeded our expectations. They asked what we wanted to prioritize in our trip and then created our itinerary around it. Communication from booking to the morning of was very detailed. Food and snacks were fresh and we loved the bbq and sides! If you’re searching for an incredible day stop here and BOOK! This IS the private excursion you’re looking for.

  5. AD

    Amaia

    Luxury 48' Leopard Catamaran in Cartagena

    Tuvimos una experiencia padrísima con este catamarán. Desde el primer contacto la comunicación fue excelente y el barco estaba impecable. La tripulación fue súper linda y atenta en todo momento; nos tocó un día con mal clima (nublado, lluvia y el mar bastante picado), pero navegaron a muy buena velocidad priorizando siempre nuestra seguridad, lo cual nos dio muchísima tranquilidad. Es un gran plus que cuenten con wifi y que puedas conectar tu propia música a las bocinas. Sin duda los volveríamos a contratar.

  6. GR

    Graham

    Luxury Afloat In Antigua Onboard Jeanneau Sun Odyssey 519 Sailboat

    Great boat/ yacht well equipped and comfortable. All organised and booked ahead of us, party of 5, arriving, captain and 1st mate ready for us and away we sailed.