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All listings in Caribbean

Awesome sailboat rentals in the Caribbean.

4.7
(2,256 Reviews)

Page 3 of 18419 listings

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!

4.5
Superowner
$1,600/day
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
$550/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
$1,144/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
🏝️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 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
⛵️ 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
60ft AIcon Yacht – Perfect for Luxury Day Trips
Events in Miami · 13 guests

60ft AIcon Yacht – Perfect for Luxury Day Trips

4.8
$350/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
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
$280/day
3.5hr Catamaran Experience Montego Bay
Sailing in Montego Bay · 30 guests

3.5hr Catamaran Experience Montego Bay

5.0
Superowner
$834/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
Sailing From Pompano Beach, FL
Sailing in Pompano Beach · 12 guests

Sailing From Pompano Beach, FL

4.6
Superowner
$125+/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
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...

4.9
Superowner
$1,000/day
34ft Pacific Seacraft Sailboat for full day Trip in Santa Marta, Magdalena
Sailing in Santa Marta · 12 guests

34ft Pacific Seacraft Sailboat for full day Trip in Santa Marta, Magdalena

5.0
$100/hour
Let's go Sailing in Miami!
Sailing in Miami · 6 guests

Let's go Sailing in Miami!

5.0
$45+/hour
Janise Sailing Afternoon Charter - Fajardo, Puerto Rico 🇵🇷
Sailing in Fajardo · 6 guests

Janise Sailing Afternoon Charter - Fajardo, Puerto Rico 🇵🇷

4.9
$995/day
Exclusive Private boat rental to any occasion in punta cana🥳
Events in El Cortecito · 30 guests

Exclusive Private boat rental to any occasion in punta cana🥳

New
Superowner
Best of 2026
$10/hour
3hr Classic Yacht Experience Montego Bay
Powerboats in Montego Bay · 35 guests

3hr Classic Yacht Experience Montego Bay

5.0
Superowner
$933/hour
Private Sailing Full Day Charter - Fajardo, Puerto Rico
Sailing in Fajardo · 6 guests

Private Sailing Full Day Charter - Fajardo, Puerto Rico

5.0
$1,995/day
🏆🎉LUXURY YACHT RENTED BY OWNER- Best 2025- 2026 Awards TOTALLY PRIVATE 🎉
Events in Verón · 100 guests

🏆🎉LUXURY YACHT RENTED BY OWNER- Best 2025- 2026 Awards TOTALLY PRIVATE 🎉

4.8
Superowner
Best of 2026
$50/hour
DELUXE BOAT FOR PRIVATE VIP BACHELORETTE/BIRTHDAY PARTY
Events in Uvero Alto · 80 guests

DELUXE BOAT FOR PRIVATE VIP BACHELORETTE/BIRTHDAY PARTY

4.5
$50/hour
Sea Ray Sundancer 38ft – Classic Luxury Cruise in Miami!
Events in Miami · 13 guests

Sea Ray Sundancer 38ft – Classic Luxury Cruise in Miami!

5.0
$100/hour

Sailing Reviews in Caribbean

  1. lb

    lauren

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

    We had a wonderful day on this boat! The captain was great, took us to the best spots for snorkeling and lunch, and we loved leaving from Orient Bay so we didn’t have to sail as long in the rougher waters. Spectacular day all around and highly recommend

  2. TL

    Tyler

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

    Amazing experience! Was the perfect addition to a bachelorette itinerary. Boat was clean, Manuel and Rene were so attentive and friendly. Cant recommend enough!

  3. RE

    Renee

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

    Great day on the ocean! We spent the day snorkeling at lle Tintamarre; swam with the turtles, explored beach and used beach toys, then sailed to Creole Rock and snorkeled -saw lots of fish and a skate…and some jellyfish (not stinging). Then we sailed to pinel island for a late lunch and beach time. Overall wonderful day!! Would do again. Service was great and extra shoutout for getting grandma in and out of the boat!

  4. Natalie

    Natalie

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

    Our group of three families from New Jersey had a full day trip to Tintamare, Creole and Pinel Islands. We had a wonderful day and great snorkeling experience. We’ve seen turtles, colorful fishes, sea urchins, beautiful jumbo sized shells, white sands, crystal clear water and crabs. The boat is comfy and gorgeous. We were absolutely lucky with the captain who was very friendly and professional. The captain also helped us to reserve Karibuni restaurant on Pinel Island and we’ve got a nice table near the water. We truly enjoyed every minute of the trip. Thank you, thank you, thank you!!

  5. SK

    Sandy

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

    If you are looking for an authentic sailing experience in Puerto Rico, look no further. This is for you! We came in with sailing experience but not in the ocean and not on as large of a boat. He let us sail the entire time and taught us along the way. Jimbo is a very experienced sailor and is looking to give you the sailing experience you are looking for. If I could have given him more than 5 stars I would have!

  6. FS

    Felicia

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

    This experience was amazing! This was the first time my family experienced a sunset ride on a sailboat and Jimbo made sure the experience was one we'd always remember. Jimbo ensured we were in the know on all safety protocols and during the sail, enlightened us with facts and history about Puerto Rico. Jimbo was personable and accommodating from the beginning to end of our excursion. This was our first, but not our last trip with Jimbo!