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All listings in Caribbean

Awesome sailboat rentals in the Caribbean.

4.8
(1,764 Reviews)

Page 1 of 20478 listings

🥂Amazing vip Catamaran in Punta Cana, Dominican Republic
Events in Bávaro · 50 guests

🥂Amazing vip Catamaran in Punta Cana, Dominican Republic

4.5
Best of 2023
$20hour
Amazing Day at Icacos & Palomino Islands
Tours in Fajardo · 6 guests

Amazing Day at Icacos & Palomino Islands

5.0
$725day
Private San Juan Bay Cruise 37' Sailboat
Sailing in San Juan · 6 guests

Private San Juan Bay Cruise 37' Sailboat

5.0
Superowner
$200hour
Luxury 48' Leopard Catamaran in Cartagena
Sailing in Cartagena · 25 guests

Luxury 48' Leopard Catamaran in Cartagena

4.8
Superowner
Best of 2023
$210-$325hour
Cruise the Caribbean Like A Rockstar with 43' Luxury Power Catamaran
Events in St. Thomas · 12 guests

Cruise the Caribbean Like A Rockstar with 43' Luxury Power Catamaran

5.0
$350hour
LUXURY CATAMARAN Barebones, Catered and All Inclusive Options
Sailing in Nassau · 12 guests

LUXURY CATAMARAN Barebones, Catered and All Inclusive Options

5.0
$700hour
46 feet luxury yacht in Montego Bay with round trip transportation!
Powerboats in Montego Bay · 14 guests

46 feet luxury yacht in Montego Bay with round trip transportation!

5.0
Best of 2023
$699hour
New addition! Lagoon 450 Catamaran
Sailing in George Town · 35 guests

New addition! Lagoon 450 Catamaran

5.0
$500hour
MAUI CATAMARAN - ISLANDS, SUNSETS AND NIGHT EVENTS
Sailing in Cartagena · 40 guests

MAUI CATAMARAN - ISLANDS, SUNSETS AND NIGHT EVENTS

5.0
Superowner
Best of 2023
$1,100day
🥰 Set sail to "Bacardi Island" Samaná ~ Private Catamaran Sailing
Sailing in Samaná Province · 12 guests

🥰 Set sail to "Bacardi Island" Samaná ~ Private Catamaran Sailing

5.0
$197hour
50ft Catamaran Charter with Water Toys - Boca Raton, FL
Sailing in Boca Raton · 12 guests

50ft Catamaran Charter with Water Toys - Boca Raton, FL

5.0
$350hour
Luxury and fun 51ft power cat from Anguilla
Powerboats in Sandy Ground · 20 guests

Luxury and fun 51ft power cat from Anguilla

5.0
$376-$429hour
SINGLAR PLUS BITCOIN LIMITED EDITION
Powerboats in Cartagena · 10 guests

SINGLAR PLUS BITCOIN LIMITED EDITION

5.0
$550day
Tour in Las Terrenas on 45ft Fountaine Pajot Sailing Catamaran
Sailing in Las Terrenas · 15 guests

Tour in Las Terrenas on 45ft Fountaine Pajot Sailing Catamaran

New
Best of 2023
$279hour
🏝️Exciting-Private Island Hopper: Affordable Charter with Crew🎉
Powerboats in Punta Cana · 100 guests

🏝️Exciting-Private Island Hopper: Affordable Charter with Crew🎉

3.0
Best of 2023
$15hour
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
Best of 2023
$600hour
Luxury Catamaran Lagoon 52' Capacity up to 40
Powerboats in Cartagena · 40 guests

Luxury Catamaran Lagoon 52' Capacity up to 40

5.0
$250hour
The 30ft in Cruises at Barbados
Sailing in Welches · 15 guests

The 30ft in Cruises at Barbados

5.0
Best of 2023
$180-$200hour
Curacao Experience, Spanish Waters, snorkel and fuik cruise ship pickup possible
Sailing in Jan Thiel · 30 guests

Curacao Experience, Spanish Waters, snorkel and fuik cruise ship pickup possible

5.0
$100person
PRIVATE BOAT-VIP EXPERIENCE-SUNSET CRUISE-BBQ 🌅🤩🛥
Events in Puerto Plata · 150 guests

PRIVATE BOAT-VIP EXPERIENCE-SUNSET CRUISE-BBQ 🌅🤩🛥

4.0
Superowner
$45person
Lagoon 450 Sailing Catamaran Charter in Collectivité de Saint-Martin
Sailing in Anse Marcel · 20 guests

Lagoon 450 Sailing Catamaran Charter in Collectivité de Saint-Martin

4.9
Best of 2023
$1,717day
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
$2,400day
The Midnight Sun,  Affordable Luxury  motor yacht
Events in Oranjestad-East · 12 guests

The Midnight Sun, Affordable Luxury motor yacht

5.0
Superowner
Best of 2023
$350hour
Private Boat Trip in punta cana
Events in El Cortecito · 80 guests

Private Boat Trip in punta cana

5.0
$60hour

Sailing Reviews in Caribbean

  1. Laura

    Laura

    Curacao Experience, Spanish Waters, snorkel and fuik cruise ship pickup possible

    Captain Daniel was a wonderful host! The boat is large and spacious with lots of places to sit and relax. There is a grill on the boat and the lunch was fabulous. Nice ride out to the sea and then relaxing in a bay by a small beach. Lots of swimming and snorkeling opportunities. Highly recommend!

  2. GM

    Geraldine

    MAUI CATAMARAN - ISLANDS, SUNSETS AND NIGHT EVENTS

    Our trip to the Rosario Islands with a group of 23 was epic! The crew was very friendly, professional, and attentive, and tried to make the best of our full day of sailing, for instance, ordering lunch beforehand for our group so we could eat as soon as we docked and could maximize swimming time on the islands. Our return ride took much longer than expected and caused splashing and rocking because of extreme winds, but the crew made sure our possessions were safely stored below and protected from getting wet, and were calm and collected during the most rough of the waves, inspiring our confidence and trust in their care. Very professional and patient crew, who got us back to port safely. Later, we realized that many of the smaller speedboats that typically go to the islands would have been even harder for our group to have traveled in in terms of sea sickness or safety, so we were grateful we booked a cat for our trip. The boat is comfortable, beautiful and perfect for a large group. I suggest discussing with the staff ahead of time for your itinerary, and factoring in time when deciding where to go to-- we were so glad to have visited the islands, but, it was a long day and others should make sure to understand how long their day will be!

  3. CF

    Connie

    Private San Juan Bay Cruise 37' Sailboat

    I had my bachelorette party with 6 women in Capt Luis' boat. I wanted a relaxing sailing experience in San Juan, as well as have the option to jump into the water, if we wanted. This was perfect for us. The water was very calm when we went. Capt Luis was good at listening to what the customer wants, and he adjusted to my preferred timeline, and I really liked that. He was very responsive via text, and email. And I would say, after doing my research and messaging a lot of boat companies, his pricing was the most reasonable and he was also the most responsive. My girls and I had a great time! The only thing I would give others a heads up is that the complimentary tapas and drinks that come with a 3-hour booking, is minimal. So if you and your guests are hungry and thirsty bunch, it is best to bring more of your own tapas/drinks. Regardless, I would still book him again as he was very professional and had great communication skills. It was an easy transaction despite my fickle mind.

  4. Fernanda

    Fernanda

    Amazing Day at Icacos & Palomino Islands

    We had an amazing experience!! Fantastic. We had a lot of fun with the seabob, we also loved our chicken skewers at lunch. Our captain was very friendly and took great care of us. Definitely, we will schedule again next time in Puerto Rico.

  5. LV

    Luis

    LUXURY CATAMARAN Barebones, Catered and All Inclusive Options

    We had a blast!! Ignacio and Jaqueline were amazing. The description of the vessel is completely accurate, and it’s evident that they love what they’re hey do. We can’t wait to book with them again. Besides, they are the only Spanish speaking crew in Bahamas which is great when traveling with Spanish speaking kids.

  6. JW

    Julie

    Private San Juan Bay Cruise 37' Sailboat

    Captain Luis and First Mate Gabi were great! It was rather windy the day we went, so we appreciated their sailing experience. Luis gave us a great tour of San Juan Harbor with lots of historical facts. Gabi was very helpful, taking care of our every need. Luis contacted us the day before with all of the details which were spot on, and we were able to order additional food and drinks so all we had to do was show up. I would highly recommend Captain Luis.