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All listings in Caribbean

Awesome paddlesport rentals in the Caribbean.

5.0
(138 Reviews)

Page 1 of 7165 listings

Private San Juan Bay Cruise 37' Sailboat
Sailing in San Juan · 6 guests

Private San Juan Bay Cruise 37' Sailboat

5.0
Superowner
$200hour
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
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
Fountaine Pajot 40ft Catamaran! African Dream, Turks and Caicos
Sailing in Leeward Settlement · 10 guests

Fountaine Pajot 40ft Catamaran! African Dream, Turks and Caicos

5.0
$728-$947hour
Luxury Catamaran Punta Cana
Events in La Romana · 150 guests

Luxury Catamaran Punta Cana

New
$70hour
Fancy Yacht Adventure with Captain and Crew in Punta Cana!
Events in Punta Cana · 160 guests

Fancy Yacht Adventure with Captain and Crew in Punta Cana!

5.0
Best of 2023
$40person
Ultimate Party with Luxury Yacht Charter for Up to 150 Guests!
Tours in Punta Cana · 150 guests

Ultimate Party with Luxury Yacht Charter for Up to 150 Guests!

5.0
$40hour
41ft Metta Sailing Catamaran in Turks and Caicos Islands
Sailing in Leeward Settlement · 12 guests

41ft Metta Sailing Catamaran in Turks and Caicos Islands

New
$450hour
44'Cruising Monohull Charter in Kralendijk, Caribbean Netherlands
Sailing in Kralendijk · 14 guests

44'Cruising Monohull Charter in Kralendijk, Caribbean Netherlands

5.0
$14hour
Celebrate in Style with Luxury Yacht Charter for 150 in Punta Cana!
Events in Punta Cana · 150 guests

Celebrate in Style with Luxury Yacht Charter for 150 in Punta Cana!

New
$40hour
Luxury Sailing Catamaran in Key West
Sailing in Key West · 10 guests

Luxury Sailing Catamaran in Key West

5.0
$250hour
Guided Clear Kayak /Paddle Board Tours and Rentals
Adventures in Leeward Settlement · 8 guests

Guided Clear Kayak /Paddle Board Tours and Rentals

New
$115person
Clear Kayak Mangrove Cay Eco Venture 2-hour tour
Adventures in Leeward Settlement · 10 guests

Clear Kayak Mangrove Cay Eco Venture 2-hour tour

New
$100person
⛵️ Relaxing ECO Day Sailing 🏝🤿🐠🧜‍♀️🍹🥂
Sailing in Fajardo · 6 guests

⛵️ Relaxing ECO Day Sailing 🏝🤿🐠🧜‍♀️🍹🥂

4.9
$400hour
Sport Cruiser Exodus Experience Tour in Montego Bay
Events in Montego Bay · 11 guests

Sport Cruiser Exodus Experience Tour in Montego Bay

5.0
$840hour
ALL INCLUSIVE Private Day and Overnight Charters
Sailing in Nassau · 28 guests

ALL INCLUSIVE Private Day and Overnight Charters

New
$700hour
1 Hour Reef Snorkeling Trip in the Sandy Reefs in Negril Sea, Jamaica
Tours in West End · 12 guests

1 Hour Reef Snorkeling Trip in the Sandy Reefs in Negril Sea, Jamaica

5.0
$120person
Discover St Maarten on this beautiful catamaran
Sailing in Upper Prince's Quarter · 15 guests

Discover St Maarten on this beautiful catamaran

5.0
$1,750day
Fort Lauderdale Bahamas Sailing Charters
Sailing in Fort Lauderdale · 6 guests

Fort Lauderdale Bahamas Sailing Charters

5.0
$119-$120hour
Custom Private Bioluminescence Kayak Tour in Fajardo
Adventures in Fajardo · 18 guests

Custom Private Bioluminescence Kayak Tour in Fajardo

New
Superowner
Best of 2023
Snoozed - Active 02 Jan 2025
Two Person Kayak Rental
Adventures in Fajardo · 2 guests

Two Person Kayak Rental

5.0
$25hour
Samana Sailing adventure: Set sail to Los Haitises National Park
Sailing in Samaná Province · 12 guests

Samana Sailing adventure: Set sail to Los Haitises National Park

New
$197hour
 Catamaran sail experience in Aruba. OPEN BAR AND BBQ included
Sailing in Oranjestad-West · 40 guests

Catamaran sail experience in Aruba. OPEN BAR AND BBQ included

New
$123person
Crewed sail catamaran for a comfortable and fun day at sea!
Sailing in Upper Prince's Quarter · 12 guests

Crewed sail catamaran for a comfortable and fun day at sea!

5.0
$1,500day

Boards & Paddles Reviews in Caribbean

  1. 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!

  2. 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.

  3. 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.

  4. LC

    Louis

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

    Deren & Crystal were exactly what we hoped for. They treated us so well and were so accommodating. They even had a happy birthday sign for me! My family and I had such a great time we added another hour onto our booking. I would highly recommend these two! It was a blast!

  5. ZZ

    Zina

    Ultimate Party with Luxury Yacht Charter for Up to 150 Guests!

    Yovannis private party boat was an experience beyond compare. From the moment our group stepped foot on the deck, we knew we were in for an unforgettable journey. The atmosphere aboard the boat was electric, with excitement palpable in the air as we set sail. The sleek and stylish design of the vessel provided the perfect backdrop for our celebration, setting the stage for an epic day on the water. The highlight was the slide that we probably took all the way throughout the trip. The crew onboard were exceptional, catering to our every whim with professionalism and enthusiasm. From serving up ice-cold drinks to guiding us through thrilling water activities, they ensured that every moment of our bachelor party was filled with excitement and adventure. Thank you Yovanni for such an unforgettable experience!

  6. LB

    Leonardo

    MAUI CATAMARAN - ISLANDS, SUNSETS AND NIGHT EVENTS

    What a great experience for a very reasonable price. The boat is even bigger than it looks in pictures and has a lot of space for seating and even to have a dance floor. Sound system was also great. Crew was very nice and served us well. Highly recommend!