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Top Jamaica Sailing Trips

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Jamaica Tours

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Montego Bay Private Yacht Tour with Open Bar and Lunch

We are not just offering a cruise. We are offering an escape and tranquility. Our aim is to provide sophistication, outstanding customer service and the …More

Montego Bay, Jamaica
4.9 (68)

Montego Bay Private Yacht Tour with Open Bar and Lunch

We are not just offering a cruise. We are offering an escape and tranquility. Our aim is to provide sophistication, outstanding customer service and the...

4 hours • Free Cancellation
4.9 (68)
from
$2,500
Zip-lining/Horseback Rides/Cat & Atv Inclusive Act with Transpo From Montego Bay

This is a private customizable day tour which Highlights the beauty of the western part of the island. This Tour is a complete package of …More

Montego Bay, Jamaica
5.0 (21)

Zip-lining/Horseback Rides/Cat & Atv Inclusive Act with Transpo From Montego Bay

This is a private customizable day tour which Highlights the beauty of the western part of the island. This Tour is a complete package of...

5 hours • Hotel pickup offered • Free Cancellation
5.0 (21)
from
$190
Bioluminescent Lagoon Tour: Night Swimming and Liming in Jamaica

This is one of the many wonders of the world. A beautiful night swim activity that all travelers to Jamaica must experience at-lease once. …More

Montego Bay, Jamaica
4.6 (58)

Bioluminescent Lagoon Tour: Night Swimming and Liming in Jamaica

This is one of the many wonders of the world. A beautiful night swim activity that all travelers to Jamaica must experience at-lease once....

1 hour 30 minutes • Hotel pickup offered • Free Cancellation
4.6 (58)
from
$80
Sail Away in Montego Bay on a Private Catamaran

Sailing along the coastline of Montego Bay offers breathtaking views and turquoise waters. You’ll have the opportunity to indulge in snorkeling and swimming, explore the …More

Montego Bay, Jamaica
5.0 (20)

Sail Away in Montego Bay on a Private Catamaran

Sailing along the coastline of Montego Bay offers breathtaking views and turquoise waters. You’ll have the opportunity to indulge in snorkeling and swimming, explore the...

3 hours • Free Cancellation
5.0 (20)
from
$1,850
4 Hours Party Boat Catamaran Cruise in Negril

Book our unique Catamaran experience. You will be picked up at your hotel. You will be travelling in a comfortable fully air conditioned vehicle from …More

Montego Bay, Jamaica
5.0 (11)

4 Hours Party Boat Catamaran Cruise in Negril

Book our unique Catamaran experience. You will be picked up at your hotel. You will be travelling in a comfortable fully air conditioned vehicle from...

4 hours • Hotel pickup offered • Free Cancellation
5.0 (11)
from
$120
Negril PRIVATE CHARTER Catamaran (rate for 21 persons)

The minimum persons required to pay is 21 The private charter can accommodate up to 120 persons You may choose any 2 stops from the …More

Negril, Jamaica
4.9 (14)

Negril PRIVATE CHARTER Catamaran (rate for 21 persons)

The minimum persons required to pay is 21 The private charter can accommodate up to 120 persons You may choose any 2 stops from the...

4 hours • Hotel pickup offered
4.9 (14)
from
$139
Sailing Adventure Cruise from Montego Bay

Let's go sailing! Imagine diving into the crystal clear waters over a coral reef filled with exotic fish, turtles and starfish. You can even participate in …More

Montego Bay, Jamaica
5.0 (6)

Sailing Adventure Cruise from Montego Bay

Let's go sailing! Imagine diving into the crystal clear waters over a coral reef filled with exotic fish, turtles and starfish. You can even participate in...

4 hours
5.0 (6)
from
$138
Party Catamaran Sunset Ricks Cafe Negril Open Bar and DJ

ARE YOU READY..!! ADULTS ONLY PARTY cruise, we sail 7 days a week, we can cater for groups of up to 140 persons. Welcome to …More

Lucea, Jamaica
4.3 (16)

Party Catamaran Sunset Ricks Cafe Negril Open Bar and DJ

ARE YOU READY..!! ADULTS ONLY PARTY cruise, we sail 7 days a week, we can cater for groups of up to 140 persons. Welcome to...

8 hours • Hotel pickup offered • Free Cancellation
4.3 (16)
from
$87
Sunset Premium 2-Hour Private Charter in Montego Bay, Open Bar

Exclusive Caribbean Sunset Escape Experience unparalleled luxury and seclusion on a 2-hour private yacht charter. Personalised Welcome Arrive at our secluded pier and enjoy: - …More

5.0 (1)

Sunset Premium 2-Hour Private Charter in Montego Bay, Open Bar

Exclusive Caribbean Sunset Escape Experience unparalleled luxury and seclusion on a 2-hour private yacht charter. Personalised Welcome Arrive at our secluded pier and enjoy: -...

2 hours • Free Cancellation
5.0 (1)
from
$280
Deluxe 2-Hour Private Charter in Montego Bay with Open Bar

Escape to a Private Paradise Begin your day with a personalised welcome at our secluded pier, where refreshing cold towels and dedicated concierge service await. …More

5.0 (3)

Deluxe 2-Hour Private Charter in Montego Bay with Open Bar

Escape to a Private Paradise Begin your day with a personalised welcome at our secluded pier, where refreshing cold towels and dedicated concierge service await....

3 hours • Free Cancellation
5.0 (3)
from
$273
Jamwest Beach Negril Family Catamaran Cruise Pick up from Lucea

The journey begins with a convenient hotel pick-up, followed by a drive to Jamwest Beach, upon arrival, you will be greeted by a host and …More

Lucea, Jamaica
3.9 (16)

Jamwest Beach Negril Family Catamaran Cruise Pick up from Lucea

The journey begins with a convenient hotel pick-up, followed by a drive to Jamwest Beach, upon arrival, you will be greeted by a host and...

3 hours 30 minutes • Hotel pickup offered • Free Cancellation
3.9 (16)
from
$95
RICKS CAFE PARTY CRUISE RIU AQUARELLE with Open Bar & DJ

ARE YOUR READY TO PARTY... this is Strictly and adults only cruise, From the moment you're picked up from the hotel your tour of Jamaica …More

Falmouth, Jamaica
4.7 (3)

RICKS CAFE PARTY CRUISE RIU AQUARELLE with Open Bar & DJ

ARE YOUR READY TO PARTY... this is Strictly and adults only cruise, From the moment you're picked up from the hotel your tour of Jamaica...

7 to 8 hours • Hotel pickup offered • Free Cancellation
4.7 (3)
from
$145
Exotic River Rafting and Luminous Lagoon Adventure

-“Rafter’s Village”, is on 6 acres of beautifully manicured lawns situated on a natural island. It offers a full recreational facility which includes picnic grounds, …More

Ocho Rios, Jamaica
5.0 (1)

Exotic River Rafting and Luminous Lagoon Adventure

-“Rafter’s Village”, is on 6 acres of beautifully manicured lawns situated on a natural island. It offers a full recreational facility which includes picnic grounds,...

4 hours • Hotel pickup offered • Free Cancellation
5.0 (1)
from
$99
Sunset Deluxe 2-Hour Private Charter in Montego Bay, Open Bar

Private Sunset Serenade Begin your exclusive 2-hour journey with a warm welcome at our secluded pier, complete with refreshing cold towels and personalised attention. Voyage …More

Sunset Deluxe 2-Hour Private Charter in Montego Bay, Open Bar

Private Sunset Serenade Begin your exclusive 2-hour journey with a warm welcome at our secluded pier, complete with refreshing cold towels and personalised attention. Voyage...

2 hours • Free Cancellation
from
$227
Premium 2-Hour Private Charter in Montego Bay with Open Bar

=Indulge in an exclusive and personalized snorkeling adventure tailored to your desires. Upon arrival at the private pier, enjoy a warm welcome with refreshing cold …More

Premium 2-Hour Private Charter in Montego Bay with Open Bar

=Indulge in an exclusive and personalized snorkeling adventure tailored to your desires. Upon arrival at the private pier, enjoy a warm welcome with refreshing cold...

3 hours • Free Cancellation
from
$327

Frequently Asked Questions

These answers are based on answers previously given to Cool Destinations customers' questions.

Recent tour reviews
Party boat
New York City
Party Catamaran Sunset Ricks Cafe Negril Open Bar and DJ
kerri_m, Aug 2026
Party boat
Great day out, loads of fun on the boat with Rex and crew. Had fun snorkelling and back on the boat for sunset
Read more
Great day trip
New York City
Party Catamaran Sunset Ricks Cafe Negril Open Bar and DJ
68dwightr, Aug 2026
Great day trip
Very lovely 💖 experience, had a great time.
Read more
It was amazing! The staff...
New York City
Montego Bay Private Yacht Tour with Open Bar and Lunch
cynthia_c, Aug 2026
It was amazing! The staff...
It was amazing! The staff was very attentive. They brought on a photographer who took amazing photos. The food was really good. Drinks were nice and strong. Worth every penny!
Read more
Our tour guide was excellent!
New York City
Bioluminescent Lagoon Tour: Night Swimming and Liming in Jamaica
Meander27273087215, Jul 2026
Our tour guide was excellent!
Amazing tour guide and transport. Always on time and our vacation was definitely enhanced by MXP tours. Highly recommend.
Read more
It was a great...
New York City
Montego Bay Private Yacht Tour with Open Bar and Lunch
Meryeha_H, Jul 2026
It was a great...
It was a great experience! They made my birthday super special! Definitely will be booking again if im ever there!
Read more
We will be back!!!
New York City
Bioluminescent Lagoon Tour: Night Swimming and Liming in Jamaica
681trinit, Jul 2026
We will be back!!!
⭐⭐⭐⭐⭐ 5/5 The Party Boat and Luminous Lagoon excursion with MXP Tours was one of the highlights of our Jamaica trip! The entire experience was well organized, fun, and unforgettable. The party boat had great music, an amazing atmosphere, and kept everyone entertained. Visiting the Luminous Lagoon afterward was absolutely breathtaking, it was such a unique experience seeing the water glow at night. The staff was friendly, professional, and made sure everyone had a great time. I highly recommend this excursion to anyone visiting Jamaica. It’s a must-do experience! 🌊✨🎉
Read more
We had an incredible week!
New York City
Deluxe 2-Hour Private Charter in Montego Bay with Open Bar
X2574GMdebh, May 2026
We had an incredible week!
We booked this tour to celebrate a 60th birthday. The staff went above and beyond our expectations. Our chef at Hanover Windward Gardens baked us a special cake, the staff on the boat provided champagne and played Happy Birthday. We all sang to the birthday girl. We all had a wonderful experience and highly recommend this tour!
Read more
Amazing charter and snorkeling experience!
New York City
Deluxe 2-Hour Private Charter in Montego Bay with Open Bar
Z7692NEsaraj, May 2026
Amazing charter and snorkeling experience!
We had the BEST time on our 2-hour private charter in Jamaica! From start to finish, the staff made the experience so fun, relaxing, and memorable. The crew brought such amazing energy, kept the vibes going the entire trip, and made everyone feel comfortable and taken care of.The snorkeling was incredible — beautiful clear water, amazing views, and such a fun experience getting to explore underwater. Everything was perfectly organized, and the staff made sure we had everything we needed while still keeping the whole trip laid-back and enjoyable.If you’re visiting Jamaica, this is 100% something you need to do. Amazing people, beautiful scenery, and such a fun way to spend the day. One of the highlights of our trip for sure!THANK YOU CAPTAIN MORGAN AND STAFF♥️
Read more
More Than a Tour — An Experience We’ll Never Forget
New York City
Sunset Premium 2-Hour Private Charter in Montego Bay, Open Bar
amiu2019, May 2026
More Than a Tour — An Experience We’ll Never Forget
Captain Morgan (Keno) and his crew were absolutely AMAZING! From the moment they picked us up right from our resort beach, everything was seamless, easy, and stress-free. Honestly, the entire experience was exactly as promised — but even BETTER!The catamaran had the perfect mix of shaded seating and sunny spots for relaxing or sunbathing while taking in the gorgeous island views. The snorkeling was incredible, and what really stood out was how attentive and caring the crew was. Safety was clearly their top priority while still making sure everyone had an unforgettable time.We had a first-time snorkeler in our group, and one of the crew members stayed nearby the entire time to make sure he felt comfortable and confident in the water. That genuine kindness and attention made such a difference.This ended up being the absolute highlight of our trip — and considering what a phenomenal vacation we had, that says a LOT! If we could give Captain Morgan and his crew 10 stars instead of 5, we absolutely would.We loved every minute of this experience and will definitely book again the next time we return to Tryall!
Read more
Perfect.
New York City
Jamwest Beach Negril Family Catamaran Cruise Pick up from Lucea
Lililacherien, Apr 2026
Perfect.
Perfection!!!! A huge thank you to the exceptional staff. My only regret was not having change to reward them. I'll never forget all that. Thank you very much.
Read more
Fritz and Lady Gaga!
New York City
Zip-lining/Horseback Rides/Cat & Atv Inclusive Act with Transpo From Montego Bay
amysF1965JA, Mar 2026
Fritz and Lady Gaga!
Fritz and Lady Gaga made the ziplomgimf trip and absolutely perfect experience! They were calm, confident, encouraging, funny, positive people and they made a find day even better!!!
Read more
Gem#2026
New York City
RICKS CAFE PARTY CRUISE RIU AQUARELLE with Open Bar & DJ
Gem_D, Feb 2026
Gem#2026
Exceptional highly recommend.. Nonstop fun, I'm in Jamaica where are you.. One Life One Love One Vibe. ❤️
Read more
Fun Excursion on the JAMWEST Catamaran Snorkel and Stop at Ricks Cafe!
New York City
Jamwest Beach Negril Family Catamaran Cruise Pick up from Lucea
GCoffiey, Jan 2026
Fun Excursion on the JAMWEST Catamaran Snorkel and Stop at Ricks Cafe!
We booked Jamwest catamaran right off the beach walking distance from the Azul Resort, Negril. Professional staff kept everyone safe throughout the snorkel trip and stop at Ricks Cafe. It was a fun trip with around 45 guests. Snorkel reef stop was nice seeing many colorful fish and sea life. We appreciate all the crew did to make it a great excursion. Fun, Fun, Fun!
Read more
Pon Di Wataaa
New York City
4 Hours Party Boat Catamaran Cruise in Negril
keyduhd, Sep 2025
Pon Di Wataaa
10/10 Experience . The music, the drinks and the vibes were unmatched then add food to the equation!!!! It was my first time swimming/snorkeling in the ocean and everyone made me feel safe! Would recommend and do again
Read more
It was a great time. I...
New York City
RICKS CAFE PARTY CRUISE RIU AQUARELLE with Open Bar & DJ
Jossilyn_D, Sep 2025
It was a great time. I...
It was a great time. I highly recommend this tour. Margaritaville was so fun. We loved cliff jumping at ricks Cafe and snorkeling was amazing as well.
Read more
This is the One!!!
New York City
Sail Away in Montego Bay on a Private Catamaran
W9647WVerica, Feb 2025
This is the One!!!
After researching several Charters we settled on Gypsy Sails due to the excellent communication, affordability for services offered and online reviews….and boy did they deliver! Just like in every other review we too had an incredible experience. The crew was very welcoming, friendly, talkative, and knowledgeable, The boat is extremely comfortable and the Captain had charted a beautiful cruise and tour of the harbor front. The snorkelling was beautiful, in crystal clear, calm waters, And the provided lunch and drinks were delicious and filling. We were a combined family of 16 ranging from 80 to 9 years old, and everyone felt comfortable and thoroughly enjoyed the experience. Highly recommend!
Read more
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