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All listings in Caribbean

Awesome sailboat rentals in the Caribbean.

4.7
(2,413 Reviews)

Page 3 of 20 • 461 listings

Private Luxury Yacht Experience in Montego Bay
Events in Montego Bay · 12 guests

Private Luxury Yacht Experience in Montego Bay

5.0
$400/hour
Punta Cana Party Cruise, Snorkeling, Slide Sand-Bar and Entertainment
Powerboats in Bávaro · 300 guests

Punta Cana Party Cruise, Snorkeling, Slide Sand-Bar and Entertainment

New
Superowner
Best of 2026
$15/hour
🤩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
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
New 2023 29ft Speedboat | Up to 12 | Cholón Party, Rosario Islands & Bathroom
Powerboats in Cartagena · 10 guests

New 2023 29ft Speedboat | Up to 12 | Cholón Party, Rosario Islands & Bathroom

4.9
$70/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
Private Deep-Sea Fishing Cabo Rojo, Dominican Republic
Fishing in Dominican Republic · 4 guests

Private Deep-Sea Fishing Cabo Rojo, Dominican Republic

New
$300/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
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
$203/hour
Limited Availability
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
⛵️  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
Luxury 42 Lagoon Catamaran Adventure in Fajardo, Puerto Rico
Sailing in Fajardo · 12 guests

Luxury 42 Lagoon Catamaran Adventure in Fajardo, Puerto Rico

5.0
$467+/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
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
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
$1,111/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
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
🏝️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
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

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. Kathy

    Kathy

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

    A glorious day at sea! Do yourself a favor and book this experience! You won’t regret it! Feeling at ease on the water and really enjoying the element was what were were striving for! As a local realtor, I make sure to enjoy what this beautiful place has to offer and this is one of them!

  4. AH

    Andrew

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

    This was a charter to remember. Charles makes the trip, with humor, attention to detail and professionalism. While he has conducted over 1100 charters, he still makes you feel valued and at ease. We had a delightful time on a perfect day and were even lucky enough to see dolphins. A rare treat. I have chartered many boats and cannot recommend him highly enough.

  5. Jill

    Jill

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

    Wonderful sail excursion on a perfect sunny day! Captain Charlie is friendly, knowledgeable and practices safe sailing in our 4 hour cruise. 1 hr in and out of Ft Lauderdale River and canals, 2 hour sail on Th open seas. Clean bathroom and plenty of room for our personal belongings, snacks and beverages.

  6. 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!!!!