We use cookies to improve your browsing experience.

And dolphins make us happy. Find out more about our cookies policy here.

Captain
All listings in Caribbean

Awesome sailboat rentals in the Caribbean.

4.8
(1,767 Reviews)

Page 1 of 20469 listings

Cabbage Key, Captiva Day Trip 1-6 people Captained
Powerboats in Cape Coral · 6 guests

Cabbage Key, Captiva Day Trip 1-6 people Captained

5.0
$95-$119hour
🥂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
$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
New addition! Lagoon 450 Catamaran
Sailing in George Town · 30 guests

New addition! Lagoon 450 Catamaran

5.0
$500hour
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
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
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
🥰 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
Luxury and fun 51ft power cat from Anguilla
Powerboats in Sandy Ground · 20 guests

Luxury and fun 51ft power cat from Anguilla

5.0
$379-$433hour
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
🏝️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
SINGLAR PLUS BITCOIN LIMITED EDITION
Powerboats in Cartagena · 10 guests

SINGLAR PLUS BITCOIN LIMITED EDITION

5.0
$550day
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
Sunset Sail in Bay of Santa Marta, Magdalena
Sailing in Comuna 2 · 12 guests

Sunset Sail in Bay of Santa Marta, Magdalena

5.0
$40person
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
Unforgettable Boat Rental Experience with FREE Captain & Fuel!
Powerboats in Fort Lauderdale · 6 guests

Unforgettable Boat Rental Experience with FREE Captain & Fuel!

5.0
$89-$129hour
4Hours-PRIVATE BOAT-VIP EXPERIENCE-SUNSET CRUISE-BBQ 🌅🤩🛥
Events in Puerto Plata · 150 guests

4Hours-PRIVATE BOAT-VIP EXPERIENCE-SUNSET CRUISE-BBQ 🌅🤩🛥

4.0
Superowner
$45person
Full-Day Yacht Adventure⭐️⭐️⭐️⭐️⭐️Fun Memories, Captain & Crew Included
Events in El Cortecito · 150 guests

Full-Day Yacht Adventure⭐️⭐️⭐️⭐️⭐️Fun Memories, Captain & Crew Included

5.0
Best of 2023
$15hour
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
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
$1,732day

Sailing Reviews in Caribbean

  1. BB

    Beth

    Luxury and fun 51ft power cat from Anguilla

    We were on Vogue from 10-4 during our visit to Anguilla and everything was honestly perfect! They do everything to make you feel special and safe and they are also lots of fun! We were able to play our own music on their speakers, full bar was excellent! Fruit was nice touch - we saw an and snorkeled as well They took us to Prickly Pear where they co texted the chef ahead of time so when we arrived we had a huge assortment of food for lunch including ribs, chicken, lobster, fish, salads and rice! Thanks for a fabulous day on the beautiful waterin Anguilla!

  2. 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!

  3. AK

    Aja

    Private San Juan Bay Cruise 37' Sailboat

    I had a great time sailing on Captain Luis’ boat! It was a nice and easy sail. We felt safe and comfortable the entire time and were well provided for. Plus, it was a great way to see the sites of Old San Juan!

  4. Ines

    Ines

    The Midnight Sun, Affordable Luxury motor yacht

    Jesus and his team were the best! They made sure we were always feel comfortable on the boat, had all the equipment we needed, and even helped us find turtles! 🐢 loved the experience, thank you for everything!

  5. 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!

  6. 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.