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Hip Strip (Gloucester Avenue)
Hip Strip (Gloucester Avenue)

Hip Strip (Gloucester Avenue) Tours and Tickets

star-5
340 Reviews

Buzzing with activity and music day and night, the Hip Strip is the beating heart of Montego Bay. This stretch of Gloucester Avenue—between Aquasol Theme Park and the airport—is the epicenter of tourism entertainment, where the town’s most popular shops, nightclubs, restaurants, bars, and beach hangouts pulsate with fun-seeking travelers.

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Gloucester Ave, Montego Bay, Jamaica
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Private and Customized Montego Bay Day Tour

Private and Customized Montego Bay Day Tour

star-5
149
Explore Montego Bay without getting lost on this personalized sightseeing tour, a great choice for a shore excursion or for first-time visitors. Travel between attractions with ease in an air-conditioned minivan and customize your itinerary according to personal preference—visit the attractions that interest you and skip the rest. Plus, round-trip transportation from your hotel or the cruise port in Montego Bay is included.
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  • 2 to 3 hours
  • Free Cancellation
From
$70.52
From
$70.52

Private Half-Day Montego Bay Tour

Private Half-Day Montego Bay Tour

star-5
9
Explore the highlights of Montego Bay in just a few hours on this personalized sightseeing tour, a great choice for a shore excursion or for first-time visitors with limited time. Visit historical sites, the Hip Strip, Margaritaville, or the beach, and customize your itinerary according to personal preference. Plus, round-trip transportation from your hotel or the port in Falmouth is included.
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  • 4 hours
  • Free Cancellation
From
$83.00
Price varies by group size
From
$83.00
Price varies by group size

Private Day Tour from Montego Bay to Negril

Private Day Tour from Montego Bay to Negril

star-5
45
Take a trip out to Negril with this private tour from Montego Bay. You'll have time to relax on the white sands of Seven-Mile Beach before continuing to Rick's Cafe, famous for its cliff divers, where you'll watch the sun set into the sea. You'll also get a chance to visit Fort Charlotte, where you'll learn about pirate history while taking in views over the sea.
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  • 7 to 8 hours
  • Free Cancellation
From
$90.00
From
$90.00

Doctor's Cave Beach, Jimmy Buffett 's Margaritaville and Shopping

Doctor's Cave Beach, Jimmy Buffett 's Margaritaville and Shopping

star-4.5
18
Experience some of the best of what Montego Bay has to offer with this tour of the coastal city. You'll have time to shop on the Hip Strip, go swimming and sunbathing at Doctor's Cave Beach, and spend time sipping margaritas (or whatever drink you order) at the Montego Bay branch of Jimmy Buffett's Margaritaville.
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  • 5 hours
  • Free Cancellation
From
$80.00
Price varies by group size
From
$80.00
Price varies by group size

Doctor's Cave Beach and Jimmy Buffet's margaritaville with shopping

Doctor's Cave Beach and Jimmy Buffet's margaritaville with shopping

star-5
1
Explore the white sand Doctor's Cave Beach, the legendary Margaritaville and stroll along the 'hip-strip' for some shopping during this day trip. With your local guide, enjoy the sun on your shoulders and the sand in your toes on the popular Doctor's Cave Beach. Head to Margaritaville to enjoy some entertainment, then walk down the bustling shopping streets for some souvenirs.
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  • 5 hours
  • Free Cancellation
From
$56.42
Price varies by group size
From
$56.42
Price varies by group size

Montego Bay Half-Day Shopping Tour

Montego Bay Half-Day Shopping Tour

star-4
40
Finding the perfect souvenir can be a challenge if you're staying in Montego Bay and already trying to experience all the city has to offer. With this tour, visit souvenir shops, a shopping mall, the Hip Strip, and Margaritaville in just a few hours and get great deals on Jamaican coffee, rum, novelty items, and more. Plus, round-trip transportation from your hotel in an air-conditioned vehicle is included.
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  • 4 hours 30 minutes
  • Free Cancellation
From
$20.00
From
$20.00

Rocklands Bird Sanctuary & City Highlights plus Shopping from Montego Bay

Rocklands Bird Sanctuary & City Highlights plus Shopping from Montego Bay

star-4.5
10
Explore the Rocklands Bird Sanctuary and visit Montego Bay's sightseeing highlights during this 5-hour tour. See the Jamaican Oriole, the White Winged Dove and Jamaica's national bird, the Doctor Bird, at the sanctuary, where they will perch on your finger and wait for you to feed them nectar from a bottle. In downtown Montego Bay, visit Sam Sharp Square, St James Parish Church and Richmond Hill Great House; then stop by one of the local 'hip strips' for some shopping. Entrance fees and round-trip transportation from Montego Bay hotels are included.
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  • 6 hours
  • Free Cancellation
From
$125.00
From
$125.00

Private Montego Bay Highlights Tour

Private Montego Bay Highlights Tour

star-5
12
Explore the landmarks and highlights of Montego Bay with a local guide on this private tour. Visit the Rose Hall Great House, shop for souvenirs and crafts on one of Montego Bay's local 'hip strips', then stop for lunch at Jimmy Buffet's world-famous Margaritaville (own expense). Journey to the top of Richmond Hill to see panoramic views of the city. Round-trip transportation by private vehicle is included.
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  • 5 hours
  • Free Cancellation
From
$90.00
From
$90.00

Local Bar Crawl Tour in Montego Bay with private transportation

Local Bar Crawl Tour in Montego Bay with private transportation

This private bar tour provides a fun-filled-100%-authentic-Jamaican-un-sugar-coated experience. The tour promotes Montego Bay’s amazing Local Bars. We will visit 6 - 7 bars and off the beaten path spots. You will easily get many opportunities to mingle and interact with the people of Montego Bay. The bars you visit are varied and interesting. Highlights may include, sunset watching great photo spots, typical Jamaican "corner bars", etc. The tour is always kept fresh and if the weather permits, you will get to experience a magnificent sunset towards the end of the tour. There will always be something new to delight you. This is a unique way to learn about our history and culture also interact with the locals who are happy to chat and share and entertain you. Feel free to ask for anything special. All travelers must be 18 years or older to drink.
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  • 2 to 3 hours
  • Free Cancellation
From
$180.00
Price varies by group size
From
$180.00
Price varies by group size

Private Montego Bay Highlights Tour with Margaritaville & Shopping

Private Montego Bay Highlights Tour with Margaritaville & Shopping

star-5
2
*Experience Montego Bay's lively hip strip for shopping and finish the day off with the entertaining Margaritaville for drinks, food and water activities. *The most affordable prices listed. *Visitors will get to experience their vacation of a lifetime beginning with their professional and trained driver who ensures safety and satisfaction at 100%. *Expect to be gifted with decades of history, shops and amenities for vacationers as the tour goes along. Guest are number one priority, hence whatever is requested shall be granted while on the tour. *Reliable, on time and guaranteed safety for a one of a kind Jamaican experience!!
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  • 1 to 6 hours
  • Free Cancellation
From
$84.11
Price varies by group size
From
$84.11
Price varies by group size

Margaritaville Hipstrip and Shopping with Private Transportation in Montego Bay

Margaritaville Hipstrip and Shopping with Private Transportation in Montego Bay

star-4.5
3
A day in the beautiful city of Montego bay were you will enjoy Margaritaville on the hipstrip enjoying good food, music and water activities then afterwards visit different gift shops for Jamaican souvenirs meet and interact with locals.
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  • 3 hours
  • Free Cancellation
From
$80.00
Price varies by group size
From
$80.00
Price varies by group size

Montego Bay Private Shopping Tour with Hotel Pickup

Montego Bay Private Shopping Tour with Hotel Pickup

star-5
12
With this tour you can visit souvenir shops, get great deals on Jamaican coffee, rum, novelty items, and more.
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  • 2 to 3 hours
  • Free Cancellation
From
$25.00
Price varies by group size
From
$25.00
Price varies by group size

Parasailing and Snorkeling Tour in Montego Bay

Parasailing and Snorkeling Tour in Montego Bay

This tour is a unique combo that allows travelers to enjoy the high adrenalin rush of parasailing followed by a calm and relaxing snorkeling experience.
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  • 2 to 4 hours
  • Free Cancellation
From
$180.00
From
$180.00

5. Montego Bay Private Highlite Sightseeing, SouvenirShoppingHalfDay Guided Tour

5. Montego Bay Private Highlite Sightseeing, SouvenirShoppingHalfDay Guided Tour

star-5
6
Let's start this wonderful tour highlight tour of Montego Bay at Sam Sharpe Square. This historic town square will allow you to experience, see and feel Montego Bay’s deep history. Your driver will take you on a guided tour throughout the city where interesting local sights will be pointed out with souvenir shopping. Fun Trip Jamaica guarantees all the other attractions, food and highlights will only enhance your love of Jamaica.
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  • 1 to 4 hours
  • Free Cancellation
From
$60.00
Price varies by group size
From
$60.00
Price varies by group size

Montego Bay Highlight Tour Visit local Community And See Local Stuffs

Montego Bay Highlight Tour Visit local Community And See Local Stuffs

star-5
4
Trust Tours Jamaica guarantee the best and most anticipated tour journey, taking on some of the top destination spots such as the city of Montego Bay and shopping along the hip strip  at the most affordable prices listed. Visitors will get to experience their vacation of  a lifetime beginning with their professional and trained driver who ensures safety and satisfaction at 100%. Expect to be gifted with decades of history, shops and amenities for vacationers as the tour goes along. Guest are number one priority, hence whatever is requested shall be granted while on the tour. Views of mountains, experiences of rivers, beaches, the cliffs,etc is always included in a tour. That is to say emphasis is put on tours that capture the island in its most natural state.
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  • 2 to 3 hours
  • Free Cancellation
From
$70.00
Price varies by group size
From
$70.00
Price varies by group size

Customize Bar Hopping Tour from Montego Bay to Bars in Montego Bay

Customize Bar Hopping Tour from Montego Bay to Bars in Montego Bay

star-5
2
A day tour of hanging out at multiple local bar in and around Montego Bay. For a local chilling and a cultural drinking experience.
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  • 3 to 4 hours
  • Free Cancellation
From
$51.29
From
$51.29

Doctor's Cave Beach, Margaritaville & Shopping from Montego Bay Hotels

Doctor's Cave Beach, Margaritaville & Shopping from Montego Bay Hotels

star-3.5
13
Explore the white sand Doctor's Cave Beach, the legendary Margaritaville and stroll along the 'hip-strip' for some shopping during this family friendly day trip. With your local guide, enjoy the sun on your shoulders and the sand in your toes on the popular Doctor's Cave Beach. Head to Margaritaville (under 18s welcome during the day) to enjoy some entertainment, then walk down the bustling shopping streets for some souvenirs. Round-trip transportation from Montego Bay and Grand Palladium hotels is included.
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  • 5 hours
  • Free Cancellation
From
$85.00
From
$85.00

Montego Bay Sightseeing and Shopping Tour

Montego Bay Sightseeing and Shopping Tour

star-5
5
Escape the tourist track to discover Montego Bay’s beautiful beaches, Reggae bars, and relaxed culture, all away from the crowds. With a dedicated guide and transport directly from your hotel, head into the hills above the town for panoramic views, then get personalized recommendations on the best beach clubs, shops, and restaurants in Montego Bay to customize your time in one of Jamaica's most popular destinations. 
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  • 3 to 4 hours
  • Free Cancellation
From
$66.67
From
$66.67

Montego Bay Highlights - Full Day Tour

Montego Bay Highlights - Full Day Tour

star-5
1
Take in all the highlights of Montego Bay in just one day with this full-day tour of the city. You'll take in panoramic views from Richmond Hill, spend time at popular Doctors Cave Beach, and hang out at Margaritaville, with plenty of time left over to walk around and shop for souvenirs.
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  • 5 to 7 hours
  • Free Cancellation
From
$85.00
Price varies by group size
From
$85.00
Price varies by group size

Rocklands Bird Sanctuary and Montego Bay Highlights Tour from Falmouth

Rocklands Bird Sanctuary and Montego Bay Highlights Tour from Falmouth

star-4
3
Explore the Rocklands Bird Sanctuary and visit Montego Bay's sightseeing highlights during this 5-hour tour departing from Falmouth. See the Jamaican Oriole, the White Winged Dove and Jamaica's national bird, the Doctor Bird, at the sanctuary, where they will perch on your finger and wait for you to feed them nectar from a bottle. In downtown Montego Bay, visit Sam Sharp Square, St James Parish Church and Richmond Hill Great House; then stop by one of the local 'hip strips' for some shopping. 
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  • 6 hours
  • Free Cancellation
From
$135.00
From
$135.00

Sightseen tour and Souvenir shopping with private transportation in Montego Bay

Sightseen tour and Souvenir shopping with private transportation in Montego Bay

star-5
1
Basically this tour offers travelers a completely private shopping experience with any hassle or bombarded with things you’re not interested in buying. This tour allows you to enjoy your shopping in comfort and peace of mind at your own expense. This also gives travelers the option to do grocery shopping, souvenir shopping, shopping at the local market for fresh produce. Or just some Jamaican food
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  • 45 minutes to 1 hour
  • Free Cancellation
From
$39.00
Price varies by group size
From
$39.00
Price varies by group size

4-Hour Memorable Montego Bay Private Tour with Sightseeing

4-Hour Memorable Montego Bay Private Tour with Sightseeing

star-5
3
Basically this tour provides a unique experience. With this product, you get to experience the city of Montego Bay while having the best herbs at your fingertips. This is a private tour where safety is our responsibility, we ensure you have a fun and memorable time. You will get a free-rolling session and experience how Jamaicans move about on a daily. Red Stripe/Herbs/Music/Memories experiencing the ultimate chill spot in Montego Bay Jamaica the Hip Stripe.
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  • 4 hours
  • Free Cancellation
From
$280.00
Price varies by group size
From
$280.00
Price varies by group size

Doctor’s Cave Beach and Margaritaville Private Tour

Doctor’s Cave Beach and Margaritaville Private Tour

Explore the white sand Doctor's Cave Beach, the legendary Margaritaville and stroll along the 'hip-strip' for some shopping during this day trip. With your local guide, enjoy the sun on your shoulders and the sand in your toes on the popular Doctor's Cave Beach. Head to Margaritaville to enjoy some entertainment, then walk down the bustling shopping streets for some souvenirs.
More
  • 5 hours
  • Free Cancellation
From
$46.16
Price varies by group size
From
$46.16
Price varies by group size

Half-Day Private Tour in Montego Bay

Half-Day Private Tour in Montego Bay

This tour is designed to give the clients an opportunity to explore the rich heritage and history of the historical city of Montego Bay and its environs. It includes shopping on the famous Hip Strip, visiting the historical and culturally rich Sam Sharpe Square in downtown Montego Bay. Sightseeing through the different communities in terms of wealthy, middle class, and low-income settings. The clients will also get the opportunity to mingle with the locals and make stops at local fruit markets and the craft market. This tour is unique due to the fact that there is so much to see and do and you don't have to spend a long time on the road travelling. At the end of the tour, you will be able to get a good understanding of aspects of our culture, entertainment, historical background, shopping and sightseeing in just under four hours. I have been during it since 1996 and will bring a special brand of expertise and knowledge to enhance the quality of the tour.
More
  • 3 to 4 hours
  • Free Cancellation
From
$35.00
From
$35.00

Filters

What people are saying about Hip-Strip-Gloucester-Avenue tours and tickets

star-5
Private and Customized Montego Bay Day Tour
"Great tour guide! We were impressed from beginning to the end. He gave us a tour that tells us about the history of the city."..."
star-5
Private Half-Day Montego Bay Tour
"we got to experience authentic Jamaica in the downtown marketplace way more than just the resort if you're adventurous and want to actually say you've been to Jamaica versus a resort in Jamaica this was an amazing experience! our tour guide Michael was amazing professional and kept us on track the restaurant we ate at was our choice and it was delicious it was called smokeez by the sea it's in neighborhood and it was the best part of the day"..."
star-5
Private Day Tour from Montego Bay to Negril
"Nigel was great, you should book this! Made my dad's birthday a great one. Thanks for being their guide."..."
star-5
Doctor's Cave Beach, Jimmy Buffett 's Margaritaville and Shopping
"The best part of the trip was the two drivers/guides. They were awesome. They were courteous , patient and knowledgeable. The beach was beautiful and we loved Margaritaville."..."
star-5
Montego Bay Half-Day Shopping Tour
"The tour was short but a nice view of Montego Bay. The ride around St. James was nice. Andre was a great tour guide!"..."
star-5
Rocklands Bird Sanctuary & City Highlights plus Shopping from Montego Bay
"I booked this for my clients and they had an Amazing time and the birds were so beautiful and friendly. They sent me a thank you saying how perfect the day was"..."
star-5
Private Montego Bay Highlights Tour
"Charles was awesome! He picked us up early in a clean SUV. We went down to Montego Bay & had a great time seeing the tourist spots as well as some of the areas the locals flock to. We felt super safe with Charles. He was knowledgeable, personable, and kept us laughing the entire time! Stopped for some delicious food & got a bunch of great pictures! Would definitely recommend to anyone!"..."
star-5
Private Montego Bay Highlights Tour with Margaritaville & Shopping
"Amazing tour of Montego Bay. My wife and I experienced the real taste of Jamaica. Traveling through the downtown market, stopped off at a local restaurant to try some authentic jerk chicken, I was true experience. Highly recommend."..."
star-5
Montego Bay Private Shopping Tour with Hotel Pickup
"Bailey was an excellent driver and tour guide. He was attentive and very customer friendly. He also went above and over by finding out where it was safe for us to party at in Jamaica with the locals."..."
star-5
Montego Bay Highlight Tour Visit local Community And See Local Stuffs
"The tour was informative. The driver was really nice and answered my questions. I really enjoyed my tour."..."
star-5
Doctor's Cave Beach, Margaritaville & Shopping from Montego Bay Hotels
"Well worth the experience. The sea is crystal clear with white soft sand. Margaritaville was lively with so much choice on their menu"..."
star-5
Montego Bay Sightseeing and Shopping Tour
"We booked this tour through Viator on Tripadvisor. We chose the 3 hour tour. I also selected to have the group tour but we still ended up with a private tour. When we first booked we were concerned that it stated we should be ready at 9am. We did not want to go that early since most things would not open up that early. I called and spoke to them and was assured that I could schedule a later time when we arrived. This was very easy once we were in Jamaica. Our hotel actually called and verified they could pick us up at 11AM. Our driver was very punctual and very informative. He asked us where we wanted to see but it was our first time in Jamaica. We did not know what there was to see so he drove us around. We went up into the mountains and saw amazing views of mobay. We went through the nicer homes and then back into downtown. It was a Sunday so we saw most stores were closed but people were selling stuff out of their cars in front of all of the closed businesses. It was really interesting to see. Our driver could have taken us anyplace but we had really just arrived and did not know so he made sure we saw many different sights. We had a 3 hour private tour, fully narrated and felt very safe at all times. We stopped at a local souvenir shop and our guide waited for us the entire time. We also asked to stop at a pharmacy and he kept an eye out to make sure we were safe while inside as well. This may not seem like a big deal but we attempted to walk off of the resort alone one day and quickly realized the value of our guide staying with us. When we return to Jamaica next year we will definitely book tours through Viator / tripadvisor again. I give our tour guide 10 stars! Thank you for a great time!!"..."
star-5
Rocklands Bird Sanctuary and Montego Bay Highlights Tour from Falmouth
"This was an awesome experience. We were able to feed the nectar to the birds which was an exhilarating experience. We then took a short walk around the mountain with our guide who was very knowledgeable about the trees and various plants. It was a great day for us because the tour also included seeing some of Montego Bay's history when we went into town and when we visited the Great House."..."
star-5
Sightseen tour and Souvenir shopping with private transportation in Montego Bay
"I had the best time Travis the tour guide made us feel very comfortable and welcomed to Jamaica. We had more fun out with him than we did at the resort. When we go to Jamaica next time we will definitely be using him❤️"..."
star-5
4-Hour Memorable Montego Bay Private Tour with Sightseeing
"Dwight, our wonderful guide showed us the real Jamaica taking us up the hills, through old town and met some very lovely and friendly folks!"..."
Frequently Asked Questions
The answers provided below are based on answers previously given by the tour provider to customers’ questions.
Q:
What's the best way to experience Hip Strip (Gloucester Avenue)?