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All listings in Jamaica

Awesome sailboat rentals in Jamaica.

5.0
(185 Reviews)

Page 1 of 228 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
$600/hour
46 feet luxury yacht in Montego Bay with unlimited cocktails and meals included
Powerboats in Montego Bay · 16 guests

46 feet luxury yacht in Montego Bay with unlimited cocktails and meals included

5.0
Superowner
Best of 2026
$599/hour
3.5hr Catamaran Experience Montego Bay
Sailing in Montego Bay · 30 guests

3.5hr Catamaran Experience Montego Bay

5.0
Superowner
$834/hour
Montego Bay Private Champagne Sunset Catamaran Cruise
Powerboats in Montego Bay · 10 guests

Montego Bay Private Champagne Sunset Catamaran Cruise

New
$1,896/hour
2.5hr Catamaran Experience Montego Bay
Events in Montego Bay · 30 guests

2.5hr Catamaran Experience Montego Bay

5.0
Superowner
$995/hour
3hr Classic Yacht Experience Montego Bay
Powerboats in Montego Bay · 25 guests

3hr Classic Yacht Experience Montego Bay

5.0
Superowner
$933/hour
Private Yacht Luxury Turquoise Adventure Ocho Rios, Jamaica
Sailing in Ocho Rios · 40 guests

Private Yacht Luxury Turquoise Adventure Ocho Rios, Jamaica

5.0
$1,560/hour
Negril Private Catamaran Cruise with Snorkeling & Drinks
Sailing in West End · 120 guests

Negril Private Catamaran Cruise with Snorkeling & Drinks

New
$509/hour
Private Group Sail and Snorkel Montego Bay
Sailing in Montego Bay · 30 guests

Private Group Sail and Snorkel Montego Bay

5.0
$940/hour
Sailing live aboard  Charter in Montego Bay, Jamaica
Sailing in Montego Bay · 15 guests

Sailing live aboard Charter in Montego Bay, Jamaica

5.0
$950/day
Private Catamaran Sail & Snorkel in Negril – Open Bar, Snacks & Music
Sailing in Negril · 60 guests

Private Catamaran Sail & Snorkel in Negril – Open Bar, Snacks & Music

New
$930+/hour
Ocho Rios Private Sunset Catamaran with Dinner & Open Bar
Powerboats in Ocho Rios · 100 guests

Ocho Rios Private Sunset Catamaran with Dinner & Open Bar

New
$817/hour
Montego Bay Private Catamaran Cruise with Open Bar & Snorkeling
Sailing in Montego Bay · 60 guests

Montego Bay Private Catamaran Cruise with Open Bar & Snorkeling

New
$1,176/hour
Montego Bay All-inclusive Yacht Experience
Events in Montego Bay · 10 guests

Montego Bay All-inclusive Yacht Experience

New
Superowner
$998/hour
Dunn’s River Falls Private Catamaran Cruise – Ocho Rios
Powerboats in Ocho Rios · 100 guests

Dunn’s River Falls Private Catamaran Cruise – Ocho Rios

New
$654/hour
Sol Brillio Negril Sailing Catamaran Rental fin Negril Westmoreland, Parish
Sailing in Negril · 100 guests

Sol Brillio Negril Sailing Catamaran Rental fin Negril Westmoreland, Parish

New
$1,800/hour
Set sail and enjoy Montego Bay’s stunning waterfront - 42 ft Catalina Sailboat
Sailing in Montego Bay · 14 guests

Set sail and enjoy Montego Bay’s stunning waterfront - 42 ft Catalina Sailboat

New
$250/hour
Mega Catamaran Charter in Ocho Rios
Sailing in Ocho Rios · 120 guests

Mega Catamaran Charter in Ocho Rios

New
$2,300/hour
Private Group Catamaran Cruise in Ocho Rios
Sailing in Ocho Rios · 40 guests

Private Group Catamaran Cruise in Ocho Rios

New
$1,266/hour
Ultra luxe Full Day Yacht Charter to Negril!
Events in Montego Bay · 10 guests

Ultra luxe Full Day Yacht Charter to Negril!

New
Superowner
$1,625/hour
Negril & Montego Bay Private Charter Sunset Catamaran Jamaica Ricks Cafe
Sailing in Hanover Parish · 120 guests

Negril & Montego Bay Private Charter Sunset Catamaran Jamaica Ricks Cafe

New
$900/hour
VIP Private Yacht Negril Jamaica | Azimut 54 Flybridge
Events in Negril · 15 guests

VIP Private Yacht Negril Jamaica | Azimut 54 Flybridge

New
$1,150/hour
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
$1,365/hour
Private Group Catamaran Sail Snorkeling Adventure in Ocho Rios, Jamaica
Sailing in Ocho Rios · 60 guests

Private Group Catamaran Sail Snorkeling Adventure in Ocho Rios, Jamaica

New
$1,080/hour

Sailing Reviews in Jamaica

  1. RM

    Renee

    46 feet luxury yacht in Montego Bay with unlimited cocktails and meals included

    I had an absolutely amazing time! I was well taken care of and pampered! Everything was wonderful from start to finish - great communication, amazing and attentive staff, delicious food, excellent service, beautiful decorations and a yummy surprise birthday cake! What a memorable birthday! Thank you all again!

  2. 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.

  3. 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 !

  4. 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.

  5. 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!

  6. CR

    Christine

    Sail away in Montego Bay! 39ft Leopard Catamaran

    This was an amazing day! We were very excited about this boat day and Stacey was excellent about communication leading up to the trip. Captain Peter and his crew also went above and beyond to make sure we had a great trip. The food, drinks, and service were perfect. They took us snorkeling which we hadn’t done in years! Our whole family got in the water and had so much fun. The weather app showed that the weather that day would be less than ideal and Stacey (days in advance) gave us the option to move days, but that day was the day that worked best for us. Captain Peter’s team tested the sea and also kept a close eye on the radar. Stacey also checked in several times. They assured us the weather would hold and the sea was safe. And it was!!! Captain Peter navigated us away from the rain and the waves. We are so glad that we trusted the team and we got to have an incredible trip!