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All listings in Caribbean

Awesome sailboat rentals in the Caribbean.

4.8
(2,081 Reviews)

Page 18 of 18415 listings

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 2025
Snoozed - Active 02 Feb 2026
Bahamas All Inclusive Luxury Day & Overnight Charter 51' Leopard Power Catamaran
Sailing in Nassau · 12 guests

Bahamas All Inclusive Luxury Day & Overnight Charter 51' Leopard Power Catamaran

4.9
Snoozed - Active 02 Mar 2026
38’ Lagoon Catamaran Charter In Miami, Florida
Sailing in Miami · 13 guests

38’ Lagoon Catamaran Charter In Miami, Florida

5.0
Snoozed - Active 02 Jan 2026
Ultimate Day Sailing Charter Onboard 40' Baba Sailboat in St. Thomas
Sailing in St. Thomas · 6 guests

Ultimate Day Sailing Charter Onboard 40' Baba Sailboat in St. Thomas

5.0
Snoozed - Active 23 Jan 2026
Sailing catamaran in USVI
Sailing in Charlotte Amalie · 6 guests

Sailing catamaran in USVI

5.0
Snoozed - Active 02 Apr 2026
Leopard 46 Catamaran Sailing in Antigua & Barbuda
Sailing in English Harbour · 6 guests

Leopard 46 Catamaran Sailing in Antigua & Barbuda

New
Snoozed - Active 02 Mar 2026
Lagoon 420 Hybrid Eco Friendly Electric Catamaran
Sailing in Guna Yala Comarca · 4 guests

Lagoon 420 Hybrid Eco Friendly Electric Catamaran

New
Snoozed - Active 31 Mar 2026

Sailing Reviews in Caribbean

  1. AJ

    Ashley

    Sail away in Montego Bay! 39ft Leopard Catamaran

    Words cannot express my gratitude towards this crew. I had been looking for private boat tours for my 30th birthday and came across this listing randomly. From day one Stacey was amazing with communication and answered any and every question that I had. The Crew was also top-tier once we got to Jamaica and on the boat. It felt like they were a part of the group. We laughed, had amazing food, had great drinks, and also several of us took a nap lol. The water was amazing and the vibes were even better. I definitely recommend this 100 times again.

  2. RH

    Ron

    Sail away in Montego Bay! 39ft Leopard Catamaran

    I rent private boats in many Caribbean islands but this has been one of the top 3 experiences ever. The captain Peter was great. With storm clouds in the sky he stayed in front of it so we would only see sun. The staff was super attentive yet gave us our space to be great. And the host Stacey is overly polite ! I plan on booking this boat everytime I go to Jamaica !

  3. LP

    Latoya

    Sail away in Montego Bay! 39ft Leopard Catamaran

    I booked with Stacey for my birthday trip to Jamaica and she did not disappoint. The boat was definitely big enough for my group of eight and there was nothing but good vibes from the crew. The snorkeling was a great addition to the beautiful views and smooth ride. We enjoyed the punch and snacks. I would Definitely book again.

  4. dwayne

    dwayne

    Sail away in Montego Bay! 39ft Leopard Catamaran

    Great day on the water! We had group of 14 people. Plenty of room to lay out and have a good time. Captain Peter and crew were awesome! The drinks stayed flowing, snorkeling was fun and beef patties for lunch were a nice touch! Would absolutely recommend!

  5. KN

    Karen

    Bahamas All Inclusive Luxury Day & Overnight Charter 51' Leopard Power Catamaran

    I had ever used this app before, but glad I did! Johnathan had amazing communication prior to our charter and was very helpful and transparent of what was included and answered all of our questions. The crew was AMAZING too! We saw sea turtles, sunfish, and more! Found a gorgeous conch shell near Rose Island and the kids LOVED the slide. The food was also AMAZING and the fully stocked bar was a winner!!! Boat was incredible and they also has sea scooters!!!

  6. LB

    Leanna

    Bahamas All Inclusive Luxury Day & Overnight Charter 51' Leopard Power Catamaran

    I truly cannot say enough great things about Anthony and Mile. From the moment we stepped on board, everything exceeded our expectations. The boat was absolutely stunning—beautifully maintained and equipped with all the fun extras that made the day unforgettable. The food was not only delicious but thoughtfully prepared and presented. Most importantly, the entire experience was filled with fun, laughter, and amazing memories. Every detail was perfect, and it was worth every single penny. Thank you both for an incredible day on the water—we’ll definitely be back!