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All listings in Caribbean

Awesome sailboat rentals in the Caribbean.

4.7
(2,407 Reviews)

Page 3 of 20 • 457 listings

🤩VIP EXPERIENCE🛥🍾ALL INCLUDED CATAMARAN 4 Bachelorette-Birthday In Punta Cana
Powerboats in Punta Cana · 80 guests

🤩VIP EXPERIENCE🛥🍾ALL INCLUDED CATAMARAN 4 Bachelorette-Birthday In Punta Cana

4.7
$85/hour
Private 29ft Island Hopping Boat for 12 | Cartagena & Rosario Islands
Powerboats in Cartagena · 10 guests

Private 29ft Island Hopping Boat for 12 | Cartagena & Rosario Islands

4.9
$500/day
Leopard 47 PC Power Catamaran Charter in Castries, St Lucia
Events in Castries · 8 guests

Leopard 47 PC Power Catamaran Charter in Castries, St Lucia

5.0
$408/hour
Sailing Charter On 39' Catalina Sailboat In Fort Lauderdale, Florida
Sailing in Fort Lauderdale · 6 guests

Sailing Charter On 39' Catalina Sailboat In Fort Lauderdale, Florida

5.0
Superowner
$119+/hour
🛥️ Make It a Yacht Day – Your Private 45ft VIP Yacht Experience in Aruba
Events in Oranjestad-East · 12 guests

🛥️ Make It a Yacht Day – Your Private 45ft VIP Yacht Experience in Aruba

5.0
$575/hour
45' Sea Ray Yacht Charter in Turks & Caicos
Powerboats in The Bight Settlement · 15 guests

45' Sea Ray Yacht Charter in Turks & Caicos

5.0
$500/hour
44ft Sailing Catamaran Charter in Bridgetown, Saint Michael
Sailing in Henrys · 20 guests

44ft Sailing Catamaran Charter in Bridgetown, Saint Michael

5.0
$202/hour
Fountaine Pajot Great Sailing Catamaran for up to 25 people!
Sailing in Cartagena · 25 guests

Fountaine Pajot Great Sailing Catamaran for up to 25 people!

4.6
Superowner
$1,600/day
44 Luxury Catamaran BIG BEN
Sailing in Leeward Settlement · 18 guests

44 Luxury Catamaran BIG BEN

5.0
$875+/hour
⛵️  MARIAH — 60’ CATAMARAN (UP TO 49 GUESTS)
Sailing in Miami Beach · 49 guests

⛵️ MARIAH — 60’ CATAMARAN (UP TO 49 GUESTS)

5.0
Superowner
$700+/hour
All Inclusive, Luxury 42 Lagoon Catamaran Adventure in Fajardo, Puerto Rico
Sailing in Fajardo · 12 guests

All Inclusive, Luxury 42 Lagoon Catamaran Adventure in Fajardo, Puerto Rico

5.0
$467+/hour
Exclusive Escape with Ocean Explorer Catamaran in Punta Cana
Powerboats in Uvero Alto · 30 guests

Exclusive Escape with Ocean Explorer Catamaran in Punta Cana

4.8
Superowner
Best of 2026
$16/hour
Private Sail Aboard Classic 1969 Sloop in San Juan, Puerto Rico
Sailing in San Juan · 6 guests

Private Sail Aboard Classic 1969 Sloop in San Juan, Puerto Rico

4.9
Superowner
$198/hour
3.5hr Catamaran Experience Montego Bay
Sailing in Montego Bay · 30 guests

3.5hr Catamaran Experience Montego Bay

5.0
Superowner
$834/hour
Lagoon 38 Catamaran trip in St Martin with skipper, departure from Orient bay
Sailing in Saint Martin · 12 guests

Lagoon 38 Catamaran trip in St Martin with skipper, departure from Orient bay

4.9
Superowner
$1,112/day
Punta Cana Booze Cruise Experience  Snorkeling • Sandbar • Music
Events in Punta Cana · 180 guests

Punta Cana Booze Cruise Experience Snorkeling • Sandbar • Music

4.0
Superowner
Best of 2026
$17/hour
Great Catamaran for Cholon, Barú, sunset cruise, lunch or dinner on board...
Sailing in Cartagena · 45 guests

Great Catamaran for Cholon, Barú, sunset cruise, lunch or dinner on board...

4.8
Superowner
$1,000/day
⛵️ Catamaran Party Boat with Captain & Crew – Up to 42 Guests!
Sailing in Miami Beach · 42 guests

⛵️ Catamaran Party Boat with Captain & Crew – Up to 42 Guests!

4.8
Superowner
$700+/hour
⛵️ Catamaran 49-Person Party Boat Includes: 1-Captain, 1-Mate and 1-Bartender
Sailing in Miami Beach · 49 guests

⛵️ Catamaran 49-Person Party Boat Includes: 1-Captain, 1-Mate and 1-Bartender

5.0
Superowner
$700+/hour
🏝️Exciting Private Yacht: Affordable Charter with Crew🎉
Events in Punta Cana · 250 guests

🏝️Exciting Private Yacht: Affordable Charter with Crew🎉

3.0
Superowner
Best of 2026
$17/hour
Private Luxury Bali 4.0 Catamaran with 3 Cabin from Old San Juan
Sailing in San Juan · 12 guests

Private Luxury Bali 4.0 Catamaran with 3 Cabin from Old San Juan

5.0
$575/hour
Lux Catamaran Fountaine Pajot 40ft
Sailing in Leeward Settlement · 10 guests

Lux Catamaran Fountaine Pajot 40ft

New
$714+/hour
Sail In Caribbean Paradise with Jeanneau Sun Odyssey 44
Sailing in Jolly Harbour · 6 guests

Sail In Caribbean Paradise with Jeanneau Sun Odyssey 44

4.9
$62+/hour
3hr Classic Yacht Experience Montego Bay
Powerboats in Montego Bay · 35 guests

3hr Classic Yacht Experience Montego Bay

5.0
Superowner
$933/hour

Sailing Reviews in Caribbean

  1. RM

    Robert

    Sailing Charter On 39' Catalina Sailboat In Fort Lauderdale, Florida

    You get the total experience when you sail with Captain Charlie and the sailboat Daffy. There is the harbor tour when leaving and returning from the ocean cruise. That is followed by an enjoyable sail off the South Florida coast--accompanied by knowledgeable commentary by Captain Charlie. He is also a most skilled sailor, as demonstrated when he outran a developing squall line to return us safe and dry to the harbor. Our group highly endorses a sailing engagement with the sailboat Daffy and Capt'n Charlie!

  2. VC

    Valerie

    🛥️ Make It a Yacht Day – Your Private 45ft VIP Yacht Experience in Aruba

    We had an absolutely amazing time with the captain and crew on Eden Luca blue. We were a group of 10 to celebrate a friend with a getaway in Aruba- and our boat trip with Eden Luca was the highlight of our trip. The crew was easy to communicate with before and the day of the trip. The soft boat deck covers for walking outside were particularly lovely - lots of seating space on the upper deck and large lounge cushions on the bow. The interior was a little dated but the crew was incredible and made sure our whole party had the best time. Our boat trip was by far the highlight of the trip!! 110%recommend.

  3. Gabriela

    Gabriela

    All Inclusive, Luxury 42 Lagoon Catamaran Adventure in Fajardo, Puerto Rico

    We had such an amazing time on our catamaran trip to Icacos! The entire experience was so much fun, and the island and water were absolutely beautiful. The crew was fantastic—super friendly, attentive, and incredibly accommodating. They made sure everyone was comfortable, having a great time, and taken care of throughout the entire trip. Everything felt relaxed, easy, and well organized. We would 100% recommend them and would absolutely book again!

  4. JP

    Jennifer

    Leopard 47 PC Power Catamaran Charter in Castries, St Lucia

    This boat rental was an absolute dream. The service was beyond incredible, the team was outstanding, and Chris went above and beyond—so responsive, organized, and genuinely kind. We explored breathtaking spots all around the island and felt completely taken care of the entire time. It was seamless, magical, and truly unforgettable. One of those experiences you’ll talk about forever.

  5. Marcus

    Marcus

    Leopard 47 PC Power Catamaran Charter in Castries, St Lucia

    One of the most fantastic experiences we’ve ever been on. It was so good that we booked the next day as well thank you to the captain and crew. They were above expectations one of the best adventures we’ve ever been on. An absolute must in St. Lucia.

  6. Chanel

    Chanel

    Leopard 47 PC Power Catamaran Charter in Castries, St Lucia

    I cannot thank these guys enough for making this boat day one to truly remember for our 30th Girls Trip!! We had an absolute ball. Meeting/pickup from the resort was seamless. The captain met us at the dock, we boarded and got situated. They dropped us off at our excursion to do the mud bath and arranged our taxi service. Then they stopped us at the beach for lunch (which was delicious) and we partied and swam in the sea for the rest of the day! Jay was an absolute angel to our group! He meshed with our personalities very well. He was hospitable, took group pictures for us that’ll last a lifetime and cooked us the best pizza that held us over til lunch. Again, thank you, thank you, thank you! If you’re considering booking this boat, RUN DONT WALK. Peace & Love, Chanel