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All listings in Caribbean

Incredible cruising catamaran rentals in the Caribbean.

4.7
(1,079 Reviews)

Page 9 of 9206 listings

Captained Charter on 47ft
Sailing in Coclé Province · 8 guests

Captained Charter on 47ft

5.0
$2,000/day
Bahia 46 in San Blas Islands
Sailing in Panama City · 8 guests

Bahia 46 in San Blas Islands

New
$1,500/night
36ft Wooden Catamaran - Enjoy a Once In a Lifetime Sailing Experience
Sailing in Naples · 6 guests

36ft Wooden Catamaran - Enjoy a Once In a Lifetime Sailing Experience

New
$200/hour
Prowler Catamaran 6pax- Fun island hoping, snorkeling and booze cruse
Powerboats in Fajardo · 8 guests

Prowler Catamaran 6pax- Fun island hoping, snorkeling and booze cruse

New
$175/hour
Hobie Cat Rental on Cockleshell Bay
Sailing in Saint George Basseterre Parish · 1 guest

Hobie Cat Rental on Cockleshell Bay

New
$100/hour
Key Largo Sailing with Dolphins on 35ft Legacy Catamaran
Sailing in Key Largo · 6 guests

Key Largo Sailing with Dolphins on 35ft Legacy Catamaran

New
$125/hour
Captained 42' Sailing Catamaran with 3 cabins and all the toys
Sailing in Key West · 6 guests

Captained 42' Sailing Catamaran with 3 cabins and all the toys

New
$320/hour
7 Day Cruise aboard Lagoon 470 Cruising Catamaran in Sainte-Anne
Sailing in Grande-Terre · 8 guests

7 Day Cruise aboard Lagoon 470 Cruising Catamaran in Sainte-Anne

New
$1,130/day
51' Neel Cruising Catamaran Rental in Le Marin, Martinique
Sailing in Rivière-Salée · 9 guests

51' Neel Cruising Catamaran Rental in Le Marin, Martinique

New
$1,535/day
Private Catamaran Charter In Punta Cana, Dominican Republic
Sailing in El Cortecito · 50 guests

Private Catamaran Charter In Punta Cana, Dominican Republic

New
$350/hour
TORTOLA BVI - PRIVATE DAY SAILS ON 48' Privilege Catamaran Charter
Sailing in Wickhams Cay 1 · 20 guests

TORTOLA BVI - PRIVATE DAY SAILS ON 48' Privilege Catamaran Charter

New
$3,000/day
Luxury Catamaran located in Downtown Miami
Sailing in Miami · 12 guests

Luxury Catamaran located in Downtown Miami

5.0
Snoozed - Active 06 May 2025
Private 65ft Catamaran for Charter Trips in Montego Bay
Sailing in Montego Bay · 40 guests

Private 65ft Catamaran for Charter Trips in Montego Bay

New
Snoozed - Active 02 Aug 2025
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

Cruising Catamaran Reviews in Caribbean

  1. Ross

    Ross

    Luxury Catamaran located in Downtown Miami

    Just Amazing!!! Aaron was professional, responsive to emails and text. He was accommodating and extremely knowledgeable. He was a gracious captain and the boat was as described. Just amazing! Highly recommend!

  2. EL

    Erin

    Luxury Catamaran located in Downtown Miami

    5 stars! The boat was so nice and Aaron customized the day based on what we wanted to do. We got to swim to a sandbar, float in the mat, tour neat coves where we saw a baby manatee. Aaron taught my teenagers how to tack and work the ropes on the sail (which was both of their favorite parts of the trip!). Plus we got to cruise the beautiful bay and see magnificent houses. Was the perfect day! Highly recommend!

  3. DD

    DANIEL

    Luxury Catamaran located in Downtown Miami

    Amazing sailing experience! Sails went up and we were cruising and had a phenomenal time! Captain Aaron is the best, very responsive beforehand to help us prepare for the day and then he took us on a memorable day trip. Don't hesitate to book, this is the one you've been looking for!

  4. YP

    Yu Yang

    Luxury Catamaran located in Downtown Miami

    Aaron was the best captain ever. We had a group of 11 guys and we all had the best time. He was extremely experienced and personalized the route exactly to the needs of our group. He has a lot of fun things on the boat like water pads and paddle boards so if you have an active group, you will be kept busy the whole time. When our friend lost his wedding ring in the water, Aaron went above and beyond and spend over 30 minutes scuba diving for it in the water.

  5. Shauna

    Shauna

    Luxury Catamaran located in Downtown Miami

    This was such a great experience! Perfect day for sailing and Aaron was awesome as we asked him all sorts of things during the charter. Laying on the trampoline and feeling the spray is a highlight we will remember forever. Thanks, Aaron! We hope to see you again.

  6. NV

    Nina

    Luxury Catamaran located in Downtown Miami

    This was truly the best choice for my group of 7 women celebrating a belated bachelorette and birthday. From booking the boat to docking back in the harbor, there was stellar communication, vessel amenities and onboard service. The boat is very well maintained, including clean equipment for water activities like snorkeling, pool noodles and stand up paddle boards. Like many others mentioned, our captain went above and beyond taking care of our group. He was super down to earth, took awesome photos and videos, steered us smoothly and gave us ample information regarding our trip. Would book again