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All listings in Caribbean

Awesome sailboat rentals in the Caribbean.

4.7
(2,379 Reviews)

Page 3 of 19439 listings

🛥️ 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
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
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
44ft Sailing Catamaran Charter in Bridgetown, Saint Michael
Sailing in Henrys · 20 guests

44ft Sailing Catamaran Charter in Bridgetown, Saint Michael

5.0
$203/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
⛵️  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
44 Luxury Catamaran BIG BEN
Sailing in Leeward Settlement · 18 guests

44 Luxury Catamaran BIG BEN

5.0
$875+/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
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
$1,133/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
3.5hr Catamaran Experience Montego Bay
Sailing in Montego Bay · 30 guests

3.5hr Catamaran Experience Montego Bay

5.0
Superowner
$834/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
Private Luxury Yacht Experience in Montego Bay
Events in Montego Bay · 12 guests

Private Luxury Yacht Experience in Montego Bay

5.0
$400/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
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
🏝️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
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
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
Sailing From Pompano Beach, FL
Sailing in Pompano Beach · 12 guests

Sailing From Pompano Beach, FL

4.6
Superowner
$125+/hour
3hr Classic Yacht Experience Montego Bay
Powerboats in Montego Bay · 35 guests

3hr Classic Yacht Experience Montego Bay

5.0
Superowner
$933/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
Let's go Sailing in Miami!
Sailing in Miami · 6 guests

Let's go Sailing in Miami!

5.0
$45+/hour

Sailing Reviews in Caribbean

  1. 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.

  2. 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!

  3. SJ

    Shea

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

    Robert and his crew went over and beyond to help celebrate my husband 50th birthday. My group of 10 fit perfectly throughout the entire boat no one was cramped, the boat was also clean and had everything we needed. Robert and his team were so attentive to our needs (my husband doesn't eat pork, we communicated that with him and he made sure our charcuterie board had other options in meat selection). This yacht experience was the highlight of our first time in Aruba!! BOOK WITH Robert- you will not be disappointed!!!!

  4. MP

    Martin

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

    My family and I recently chartered a yacht in Aruba to celebrate our daughter's birthday and we could not have been more thrilled with our experience. The crew on board went above and beyond to ensure that every detail was perfect for our special day. From the moment we stepped on board, we were greeted with smiles and warmth, and they had even gone the extra mile to decorate the boat with birthday balloons and all the special touches we had requested. Throughout the day, the crew was attentive, friendly, and made sure that we had everything we needed to have a fantastic time out on the ocean. They truly went out of their way to make our experience unforgettable and we felt incredibly well taken care of. I would highly recommend this yacht to anyone looking for a luxurious and fun-filled day out on the water. The crew's exceptional service and attention to detail really set this experience apart and I can't wait to charter this yacht again the next time we are in Aruba. Five stars all the way!

  5. Julia

    Julia

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

    We had an AMAZING time. This boat is even more beautiful than the photos show. We had insulated cups for our drinks which was such a great touch. We relaxed, snorkeled a bit and were waited on with the best service. The crew was diligent with refilling our drinks and asking what we needed. They were lovely and we would highly recommend!

  6. 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.