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All listings in Jamaica

Awesome sailboat rentals in Jamaica.

5.0
(160 Reviews)

Page 1 of 121 listings

Jeanneau Sun Odyssey for an Intimate Cruise in Montego Bay
Sailing in Montego Bay · 4 guests

Jeanneau Sun Odyssey for an Intimate Cruise in Montego Bay

5.0
$417/hour
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
$600/hour
46 feet luxury yacht in Montego Bay with round trip transportation!
Powerboats in Montego Bay · 16 guests

46 feet luxury yacht in Montego Bay with round trip transportation!

5.0
Best of 2025
$699/hour
2.5hr Catamaran Experience Montego Bay
Events in Montego Bay · 30 guests

2.5hr Catamaran Experience Montego Bay

5.0
Superowner
Best of 2025
$995/hour
3.5hr Catamaran Experience Montego Bay
Sailing in Montego Bay · 30 guests

3.5hr Catamaran Experience Montego Bay

5.0
Superowner
Best of 2025
$834/hour
3hr Classic Yacht Experience Montego Bay
Powerboats in Montego Bay · 25 guests

3hr Classic Yacht Experience Montego Bay

5.0
Superowner
Best of 2025
$933/hour
Sail Away In Negril With 39ft Leopard Catamaran
Sailing in Negril · 16 guests

Sail Away In Negril With 39ft Leopard Catamaran

5.0
Superowner
Best of 2025
$900/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
Montego Bay All-inclusive Yacht Experience
Events in Montego Bay · 10 guests

Montego Bay All-inclusive Yacht Experience

New
Superowner
Best of 2025
$998/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
Private Yacht Luxury Turquoise Adventure Ocho Rios, Jamaica
Sailing in Ocho Rios · 40 guests

Private Yacht Luxury Turquoise Adventure Ocho Rios, Jamaica

New
$1,560/hour
Mega Catamaran Charter in Ocho Rios
Sailing in Ocho Rios · 120 guests

Mega Catamaran Charter in Ocho Rios

New
$4,128/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
Best of 2025
$1,625/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
$1,000/hour
Cruising Catamaran Charter in Falmouth
Sailing in Falmouth · 40 guests

Cruising Catamaran Charter in Falmouth

New
$1,250/hour
Private Sunset Cruise With Dinner Ocho Rios, Jamaica
Events in Ocho Rios · 30 guests

Private Sunset Cruise With Dinner Ocho Rios, Jamaica

New
$1,175/hour
Reggae Catamaran Negril Sail Snorkel and Sunset Tour
Sailing in West End · 20 guests

Reggae Catamaran Negril Sail Snorkel and Sunset Tour

New
$1,084/hour
Axe 1 Center Console Boat Rental in Montego Bay, Jamaica
Events in Montego Bay · 8 guests

Axe 1 Center Console Boat Rental in Montego Bay, Jamaica

New
Snoozed - Active 02 Aug 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

Sailing Reviews in Jamaica

  1. ML

    Michelle

    Jeanneau Sun Odyssey for an Intimate Cruise in Montego Bay

    Sailing with the Captain and his son was really nice. They are friendly and professional, very accommodating. The vibe was amazing, from the tasty drinks, to the delicious sushi. My family had a great time snorkeling.

  2. AP

    Andy

    3hr Classic Yacht Experience Montego Bay

    If in Jamaica you must take this boat out on the Bay! The staff made our experience unforgettable. My kids got to snorkel, jump off the boat, and dance to music of their choice from our private DJ. Can't wait to get back on this vessel!

  3. Kacey

    Kacey

    Sail away in Montego Bay! 39ft Leopard Catamaran

    Stacey was amazing. She provided a memorable experience, felt like home, and had fun with us too. She prioritized our memories and fun. She’s the best.

  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!