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All listings in Caribbean

Awesome sailboat rentals in the Caribbean.

4.7
(2,411 Reviews)

Page 1 of 20 • 460 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
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
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
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
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
$1,786/day
23’ Bayliner Beautiful Boat In Miami
Sailing in Miami · 9 guests

23’ Bayliner Beautiful Boat In Miami

4.9
$90/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
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
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
Catamaran in Saint George's
Sailing in Saint George's · 55 guests

Catamaran in Saint George's

4.9
$174+/hour
The 30ft in Cruises at Barbados
Sailing in Welches · 12 guests

The 30ft in Cruises at Barbados

5.0
$180+/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
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
🥳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
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
⛵️ Catamaran Party Boat 50' (49-Person)
Sailing in Miami Beach · 42 guests

⛵️ Catamaran Party Boat 50' (49-Person)

5.0
Superowner
$700+/hour
Memorable Punta Cana Boat Party Awaits! Inquire our Private Yacht Charter now!
Events in Punta Cana · 300 guests

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

5.0
Superowner
Best of 2026
$15/hour
Cabbage Key, Captiva Day Trip 1-6 people Captained 24' Hurricane Deck Boat
Powerboats in Cape Coral · 6 guests

Cabbage Key, Captiva Day Trip 1-6 people Captained 24' Hurricane Deck Boat

5.0
$100+/hour
Charter the Lagoon 450 Cruising Catamaran for Anguilla Tours with Friends
Sailing in Saint Martin · 20 guests

Charter the Lagoon 450 Cruising Catamaran for Anguilla Tours with Friends

5.0
$2,010/day

Sailing Reviews in Caribbean

  1. 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.

  2. 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!

  3. 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.

  4. 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.

  5. TL

    Tony

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

    One of the better charters I've done. Aaron was responsive before the trip, the boat was in excellent shape, and he made the whole day effortless — no stress, no surprises. If you're deciding, book it. Five stars.

  6. MG

    Manuel

    23’ Bayliner Beautiful Boat In Miami

    An excellent experience! We had a fantastic day. The boat was spotless, comfortable, and exactly as agreed. The service was top-notch from start to finish. 100% recommended I would definitely do it again! See you soon. ⭐️⭐️⭐️⭐️⭐️⭐️⭐️⭐️⭐️⭐️