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Montego Bay Tours

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Private Yacht Tour w/optional Flying Dress Photoshoot Montego Bay

Luxurious Ultimate Private Caribbean Vacation Package!! 3-hour cruise includes: Various refreshments, including (Premium Alcohol and Rum Punch). Choice of KFC Chicken (includes fries, biscuits) or …More

Private Yacht Tour w/optional Flying Dress Photoshoot Montego Bay

Luxurious Ultimate Private Caribbean Vacation Package!! 3-hour cruise includes: Various refreshments, including (Premium Alcohol and Rum Punch). Choice of KFC Chicken (includes fries, biscuits) or...

3 hours • Hotel pickup offered • Free Cancellation
from
$2,844
Montego Bay Photographer LLC - Kevin Wright

Take part in your exclusive wedding photography with Jamaica wedding photographer Kevin Wright. You will be the star of the show on this exciting photography …More

Likely to Sell Out
Likely to Sell Out
5.0 (11)

Montego Bay Photographer LLC - Kevin Wright

Take part in your exclusive wedding photography with Jamaica wedding photographer Kevin Wright. You will be the star of the show on this exciting photography...

8 hours • Hotel pickup offered • Free Cancellation
5.0 (11)
from
$1,700
Flying Dress Photoshoots in Montego Bay Jamaica

Take part in your exclusive Flying Dress Photoshoot in Jamaica with Kevin Wright's team of professional photographers. You will be the star of the show …More

5.0 (48)

Flying Dress Photoshoots in Montego Bay Jamaica

Take part in your exclusive Flying Dress Photoshoot in Jamaica with Kevin Wright's team of professional photographers. You will be the star of the show...

1 to 2 hours • Free Cancellation
5.0 (48)
from
$500
Jamaica Flying Dress Photoshoots

Feel like a million bucks and book your Jamaica Flying Dress Photoshoot with Kevin Wright. Perfect gift for anniversary, birthday, girls trip. Please bring your …More

4.3 (11)

Jamaica Flying Dress Photoshoots

Feel like a million bucks and book your Jamaica Flying Dress Photoshoot with Kevin Wright. Perfect gift for anniversary, birthday, girls trip. Please bring your...

1 to 2 hours
4.3 (11)
from
$450
Explore Montego Bay to River Tubing, Horse Back Riding, Blue Hole

This is a Private and customize HASSLE FREE and CASHLESS Day Tour, to a full day attraction in Ocho Rios that does encounter in a …More

4.9 (14)

Explore Montego Bay to River Tubing, Horse Back Riding, Blue Hole

This is a Private and customize HASSLE FREE and CASHLESS Day Tour, to a full day attraction in Ocho Rios that does encounter in a...

8 to 9 hours • Hotel pickup offered • Free Cancellation
4.9 (14)
from
$404
Clear Water Kayaking Photo shoot In Montego Bay

Crystal clear kayaks offer a unique and thrilling way to glamorize and enjoy everyday life, this gives you a sitting on water" vibes! Come enjoy …More

5.0 (1)

Clear Water Kayaking Photo shoot In Montego Bay

Crystal clear kayaks offer a unique and thrilling way to glamorize and enjoy everyday life, this gives you a sitting on water" vibes! Come enjoy...

30 minutes • Hotel pickup offered • Free Cancellation
5.0 (1)
from
$300
Private Martha Brae Raft and Luminous Lagoon Tour with Dinner

Experience a romantic evening with your love one away from your resort. are you or your love one celebrating your anniversary, a birthday, Honeymoon etc? …More

5.0 (2)

Private Martha Brae Raft and Luminous Lagoon Tour with Dinner

Experience a romantic evening with your love one away from your resort. are you or your love one celebrating your anniversary, a birthday, Honeymoon etc?...

4 hours • Hotel pickup offered • Free Cancellation
5.0 (2)
from
$270
Explore Montego Bay Jamaica to Pelican Bar & Appleton Rum Factory

This is a CASHLESS AND HASSLE FREE Day Tour, starts from Montego Bay goes through the mountainous terrain of Jamaica south coast, and passes under …More

5.0 (11)

Explore Montego Bay Jamaica to Pelican Bar & Appleton Rum Factory

This is a CASHLESS AND HASSLE FREE Day Tour, starts from Montego Bay goes through the mountainous terrain of Jamaica south coast, and passes under...

8 to 10 hours • Hotel pickup offered • Free Cancellation
5.0 (11)
from
$269
Explore Montego Bay Jamaica Luxury Round TTransfer in Montego Bay

After a hard working period and on a vacation in Jamaica, it’s a freedom moment of fun and enjoyment to have someone to take you …More

5.0 (8)

Explore Montego Bay Jamaica Luxury Round TTransfer in Montego Bay

After a hard working period and on a vacation in Jamaica, it’s a freedom moment of fun and enjoyment to have someone to take you...

15 to 25 minutes • Hotel pickup offered • Free Cancellation
5.0 (8)
from
$253
Explore Montego Bay to Bob Marley Mausoleum Nine Miles& Blue Hole

This is a CASHLESS HASSLE FREE TOUR that Pickup from Cruise Ship or Hotel in Private style, breaking away from coach and large bus group …More

5.0 (2)

Explore Montego Bay to Bob Marley Mausoleum Nine Miles& Blue Hole

This is a CASHLESS HASSLE FREE TOUR that Pickup from Cruise Ship or Hotel in Private style, breaking away from coach and large bus group...

7 to 8 hours • Hotel pickup offered • Free Cancellation
5.0 (2)
from
$250
Explore Montego Bay Jamaica to Country Side Appleton & Y S Falls

This is a cashless hassle free day tour that goes through the mountainous terrain of Jamaica south coast, and passes under over lapping tunnel of …More

5.0 (4)

Explore Montego Bay Jamaica to Country Side Appleton & Y S Falls

This is a cashless hassle free day tour that goes through the mountainous terrain of Jamaica south coast, and passes under over lapping tunnel of...

8 to 10 hours • Hotel pickup offered • Free Cancellation
5.0 (4)
from
$250
Explore Montego Bay Jamaica to Blue Hole/Falls & River Rapid Tour

This is a one of a kind two in one HASSLE FREE CASHLESS DAY TOUR that offers tour from Montego Bay at a very affordable …More

5.0 (6)

Explore Montego Bay Jamaica to Blue Hole/Falls & River Rapid Tour

This is a one of a kind two in one HASSLE FREE CASHLESS DAY TOUR that offers tour from Montego Bay at a very affordable...

7 hours • Free Cancellation
5.0 (6)
from
$231
Explore Montego Bay Jamaica, Horse Back Riding & Blue Hole Falls

This’s a easy access and CASHLESS HASSLE FREE DAY TOUR. That’s inclusive of Horse Back riding tour and Blue Hole River/falls fun fill day in …More

5.0 (9)

Explore Montego Bay Jamaica, Horse Back Riding & Blue Hole Falls

This’s a easy access and CASHLESS HASSLE FREE DAY TOUR. That’s inclusive of Horse Back riding tour and Blue Hole River/falls fun fill day in...

7 to 8 hours • Hotel pickup offered • Free Cancellation
5.0 (9)
from
$231
Bamboo Rafting with Limestone Massage at Lethe

If you have a deep appreciation for the beauty of nature, I warmly invite you to embark on a journey with me to Lethe Bamboo …More

5.0 (7)

Bamboo Rafting with Limestone Massage at Lethe

If you have a deep appreciation for the beauty of nature, I warmly invite you to embark on a journey with me to Lethe Bamboo...

2 hours • Hotel pickup offered • Free Cancellation
5.0 (7)
from
$200
Luxury Montego Bay Airport Taxi

Start your Jamaican getaway the right way with a luxury private transfer from Montego Bay Airport straight to your resort. No waiting in long lines, …More

5.0 (2)

Luxury Montego Bay Airport Taxi

Start your Jamaican getaway the right way with a luxury private transfer from Montego Bay Airport straight to your resort. No waiting in long lines,...

5 to 15 minutes • Free Cancellation
5.0 (2)
from
$200
Luxury MBJ Airport Transfer to Montego Bay Hotels

Private luxury transportation, We service all major international airports, seaports, and private terminals. We offer close protection services and engage in event planning Destination weddings …More

Likely to Sell Out
Likely to Sell Out
5.0 (10)

Luxury MBJ Airport Transfer to Montego Bay Hotels

Private luxury transportation, We service all major international airports, seaports, and private terminals. We offer close protection services and engage in event planning Destination weddings...

1 to 24 hours • Free Cancellation
5.0 (10)
from
$180
Montego Bay VIP Drive Tour with Bryan Ottey

Join Bryan for an unforgettable journey through Montego Bay with friends and family on a private VIP drive tour. Experience a perfect blend of shopping, …More

Likely to Sell Out
Likely to Sell Out
5.0 (4)

Montego Bay VIP Drive Tour with Bryan Ottey

Join Bryan for an unforgettable journey through Montego Bay with friends and family on a private VIP drive tour. Experience a perfect blend of shopping,...

4 hours • Hotel pickup offered • Free Cancellation
5.0 (4)
from
$180
Couples Clear Kayak Photoshoot in Montego Bay

Experience a unique and memorable couples' photoshoot on the crystal-clear waters of Jamaica. This package includes 30 photos taken during your session, with 7 of …More

4.5 (2)

Couples Clear Kayak Photoshoot in Montego Bay

Experience a unique and memorable couples' photoshoot on the crystal-clear waters of Jamaica. This package includes 30 photos taken during your session, with 7 of...

30 minutes • Hotel pickup offered • Free Cancellation
4.5 (2)
from
$180
Clear Kayak Beauty Photoshoot Montego Bay Jamaica

We go above and beyond to make sure our customers receive the best images. Clients photos are taken with High-Resolution drone camera. You can't help …More

5.0 (100)

Clear Kayak Beauty Photoshoot Montego Bay Jamaica

We go above and beyond to make sure our customers receive the best images. Clients photos are taken with High-Resolution drone camera. You can't help...

30 minutes • Hotel pickup offered • Free Cancellation
5.0 (100)
from
$160
Explore Montego Bay Jamaica Tour to Dunns River Falls

This is a hassle free tour that INCLUDES ROUND TRIP TRANSPORTATION AND ENTRANCE FEES in the cost. We pickup from Cruise Ships Piers or hotel …More

5.0 (14)

Explore Montego Bay Jamaica Tour to Dunns River Falls

This is a hassle free tour that INCLUDES ROUND TRIP TRANSPORTATION AND ENTRANCE FEES in the cost. We pickup from Cruise Ships Piers or hotel...

6 to 8 hours • Hotel pickup offered • Free Cancellation
5.0 (14)
from
$154

Frequently Asked Questions

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

Recent tour reviews
Highlight of my trip on the water!!
New York City
Clear Kayak Beauty Photoshoot Montego Bay Jamaica
michellefR2554IB, Sep 2026
Highlight of my trip on the water!!
Absolutely loved my Kodak photo shoot! It was hands down the highlight of my trip. The team made everything so easy and fun, captured every shot beautifully, and even created a video that brought the whole experience to life. I’m beyond thrilled with how everything turned out, and can’t recommend them enough.
Read more
Tripping in JA
New York City
Clear Kayak Beauty Photoshoot Montego Bay Jamaica
abigayed2026, Sep 2026
Tripping in JA
My clear kayak and fly dress photoshoot experience in Montego Bay was absolutely unforgettable! From start to finish, everything was beautiful, fun, and so much more.The clear kayak was such a unique experience. Being out on the gorgeous water made the experience feel magical. The entire experience was fun, relaxing, and full of positive energy. The scenery was breathtaking, the water was beautiful, and the photos captured the moment perfectly. The Austine was friendly, helpful, and made me feel comfortable throughout the shoot. If you're visiting Montego Bay and looking for something different, fun, and Instagram-worthy, I highly recommend doing the clear kayak photoshoot with him. It’s an experience you’ll remember long after your vacation is over. Experience 10/10
Read more
An Amazing Jamaican Experience
New York City
Explore Montego Bay Jamaica to Pelican Bar & Appleton Rum Factory
ryanpH3493FO, Jun 2026
An Amazing Jamaican Experience
Leon and Nigel shared fantastic stories and experiences on the way to Floyd’s Pelican Bar. On the way there, the devastation from the hurricane the year before was still overwhelming — but how amazing was it to make it out to the sandbar and be in a restaurant that was almost like a metaphor for Jamaica?! They’re rebuilding their home, and keeping it as special as it was before. (See if you can find our carving, and you should absolutely do your own.) Also, the food is so delicious!It was a truly unique experience, and they’ve aptly named their touring agency. We highly recommend their services.
Read more
Awesome Food and Great Experience
New York City
Explore Montego Bay Jamaica to Pelican Bar & Appleton Rum Factory
U672OGkayp, Jun 2026
Awesome Food and Great Experience
Went to Pelican Bar on the recommendation of our driver Nigel. Leon and Nigel made the experience incredible. The boat ride to the bar was really cool. The food at the Pelican Bar was so delicious! We had a great time, and our drivers spent a lot of time with us and made sure we enjoyed everything.
Read more
Amazing service
New York City
Luxury MBJ Airport Transfer to Montego Bay Hotels
jacquelinecL6088TS, Jun 2026
Amazing service
We did transportation from Montego Bay airport to Negril, round-trip upon arrival we were greeted very warmly by Raymond. He loaded up our luggage and waywe went. We were safely, transported to our hotel, with lots of informative commentary by Raymond. He answered all of our questions about the locals, the , food to try, and much more. He is a great conversationalist, and extremely warm and welcoming man. On the way back, we were taken by Junior to the airport. He picked us up in a very luxurious car that was spotless and extremely comfortable with reclining seats in the back. Jr has a very friendly personality, and was a wealth of knowledge. T.E.A.M. transport is my go to transportation anytime I am in Jamaica. We have had the pleasure of using them multiple times over the last 10 years. If you want protected, safe transportation, to any destination, this is the company you should hire.
Read more
Amazing!!!
New York City
Luxury Montego Bay Airport Taxi
Bella J, May 2026
Amazing!!!
Island dreamers were amazing! Super efficient and on time.
Read more
Family of 6 private transfer from airport to hitrl
New York City
Luxury Montego Bay Airport Taxi
NY8486, Feb 2026
Family of 6 private transfer from airport to hitrl
Family of 6 traveling to grand palladium. We had excellent private service. Will book them again.
Read more
Dunns River tour
New York City
Explore Montego Bay Jamaica Tour to Dunns River Falls
fff124, Sep 2025
Dunns River tour
We had an awesome time on the tour arranged to Dunns River waterfalls on the 25 August 2025. We were a large group of 210 people and our tour guide Leon was exceptional. He arrived promptly with adequate transportation and took us all at the experience on time. We had a great day with no issues and everyone returned back safely to our hotel. I would highly recommend his company
Read more
Fantastic Travel Guide Experience!
New York City
Montego Bay VIP Drive Tour with Bryan Ottey
Trek54905454749, Jul 2025
Fantastic Travel Guide Experience!
I had a wonderful experience with our travel guide! Communication was smooth and easy from the start, and they were incredibly friendly and professional throughout. They took the time to really listen and understand what my son and I were looking for in our trip, and put together an itinerary that was thoughtful, well-paced, and full of great experiences. Every detail was carefully considered, which made everything run seamlessly. Always punctual and prepared, our guide made the whole journey stress-free and enjoyable. I highly recommend their services to anyone looking for a well-organized, personal, and memorable travel experience!
Read more
From the start, out...
New York City
Couples Clear Kayak Photoshoot in Montego Bay
Danyaal_S, Jun 2025
From the start, out...
From the start, out driver Keemo was very welcoming and polite, showed up on time and was very informative throughout our journey. Once we arrived at the location, the camera men were very professional and guided us through different poses which resulted in some great photos. I would definitely recommend! Great experience!
Read more
SPEECHLESS
New York City
Jamaica Flying Dress Photoshoots
Mjhenville, Jun 2025
SPEECHLESS
✨️Still SPEECHLESS! ✨️✨️My Jamaica flying dress shoot was a literal dream come true💫💫✨️✨️Booking a flying dress photo shoot in Jamaica was one of the highlights of my trip - and working with Kevin made it absolutely seamless and unforgettable. From the very first call, Kevin was AMAZING -super responsive, professional, and s From the very first call, Kevin was professional, and so thoughtful. He handled every single detail and even came to our villa for the shoot (yes, he traveled to us - talk about service! 👏)Before the shoot, Kevin sent a selection of gorgeous dress colors to choose from and bonus: the dresses are fully adjustable, so they flatter every shape.The shoot itself? Pure magic. ✨️💫The team was SO patient, kind, and creative guiding me with poses, fixing the dress, catching the breeze at just the right moment. They gave 110% to get the perfect shot, and WOWWWWW. .. did they deliver.Massive love to Kevin & the team. If you're in Jamaica and dreaming of that flying dress moment... BOOK THEM NOW. You will not regret it!
Read more
Must Book with Leon
New York City
Explore Montego Bay Jamaica Tour to Dunns River Falls
jcR4608TJ, May 2025
Must Book with Leon
On this tour, Leon was engaging and made you feel you can be yourself. Very safe driver! Very knowledgeable of Jamaica! He knows many people and you can tell he is well like and respected! This made you know and feel you were with a good person! This is important when you are in an area you know nothing about. Also, before even leaving for our destination he made sure we had what was needed to make our experience smooth. Since we already used him for airport transportation, we knew we could ask any questions via WhatsApp and we would get a prompt response. We did not have waterproof pouch for a phone, but he did! Though we knew our destination, Leon encouraged us to stop at a souvenir shop and then when we told him we wanted to try KFC he found a way to work it in! If you let him know something you heard about or want to try, he was going to do what he can to make it happen! Once at your destination, he stays! This is fabulous because you know if anything happens you have a reliable, knowledgeable person that can help! On top of all this, the Falls are a must climb! Definitely is a memorable experience!
Read more
Exceptional service!
New York City
Montego Bay VIP Drive Tour with Bryan Ottey
Passenger03857563589, May 2025
Exceptional service!
Brian delivered outstanding service for my family of seven from start to finish. From the moment he picked us up and drove us to our resort in Ocho Rios, he went above and beyond, offering a rich, informative tour along the way and sharing fantastic local recommendations for activities and places to visit during our stay in Jamaica. Two days later, he transported us to Kingston with the same level of excellence and professionalism. Throughout the journey, he made thoughtful stops at local restaurants, souvenir shops, and points of interest, giving us an authentic taste of Jamaica while always prioritizing our comfort and safety. Brian’s driving is both skilled and cautious; he clearly respects the rules of the road and ensures a smooth, secure ride. I would wholeheartedly recommend his services to anyone planning a trip. His knowledge, hospitality, and genuine care made a memorable impact on our vacation.
Read more
Excellent tour guide
New York City
Private Martha Brae Raft and Luminous Lagoon Tour with Dinner
399whitneyr, Apr 2025
Excellent tour guide
Kyle was a wonderful tour guide . He was professional , timely, and very friendly . I traveled as a single woman with children and he made us feel safe at all times . He was helpful in recommending food as well as activities. I highly recommend booking with Esteen tours. I will definitely choose them every time I come to Jamaica .
Read more
New York City
Luxury MBJ Airport Transfer to Montego Bay Hotels
Cat_L, Jan 2025
"Exceptional Last-Minute Luxury Transportation Experience in Jamaica
I had an exceptional experience with a transportation company in Jamaica, thanks to Raymond, the owner. At the last minute, he arranged luxury transportation from my resort to the airport. A Mercedes sedan and a professional driver were ready and waiting for me at checkout. My driver was incredibly friendly and helpful, taking care of my bags and ensuring I was comfortable. It truly felt like a five-star service. Raymond even arranged for an attendant to meet me at the airport, assisting me with my luggage check-in and guiding me through customs. As a travel professional, I highly recommend this company for all your luxury transportation needs.
Read more
Leon is the best
New York City
Explore Montego Bay Jamaica Luxury Round TTransfer in Montego Bay
K1440PGseans, Sep 2024
Leon is the best
Leon is a great choice! He truly cares about your safety, happiness and experience in Jamaica! Let him know what you want to do and he'll make it happen!
Read more
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