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

Hip Strip (Gloucester Avenue) Tours and Tickets

star-5
409 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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41 results

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

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

star-4.5
20
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

Private and Customized Montego Bay Day Tour

Private and Customized Montego Bay Day Tour

star-5
165
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
13
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
$64.29
Price varies by group size
From
$64.29
Price varies by group size

Private Day Tour from Montego Bay to Negril

Private Day Tour from Montego Bay to Negril

star-5
73
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

Montego Bay Half-Day Shopping Tour

Montego Bay Half-Day Shopping Tour

star-4
42
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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  • 3 hours
  • Free Cancellation
From
$30.00
From
$30.00

The Amazing Montego Bay City Tour

The Amazing Montego Bay City Tour

star-5
4
Experience a deeper look into the city of Montego Bay from this tour journey. Learn of its history and feel the vibe of the tourism capital of Jamaica. Take a drive through different class of communities and get to meet the locals and see the city's business and social scenes. You may stop for food at your desired local restaurant, visit the Doctors Cave Beach if you wish or lounge spots such as 27/27 on Montego Bay's Hip Strip Lastly you can shop until you drop. We'll stop on the Montego Bay Hip strip which is known for its liveliness and vibrancy in the city. We'll visit gift shops so you can purchase souvenirs to bring back home in remembrance of Jamaica and the amazing excursion you did.
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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

Montego Bay Private Shopping Tour with Hotel Pickup

Montego Bay Private Shopping Tour with Hotel Pickup

star-5
16
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
$30.00
Price varies by group size
From
$30.00
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-4
5
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 Highlights

Montego Bay Highlights

star-5
4
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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  • 3 to 5 hours
  • Free Cancellation
From
$85.00
Price varies by group size
From
$85.00
Price varies by group size

Combo Day Trip to Bob Marley Nine Mile and Hip Strip with Shops and Dispensary

Combo Day Trip to Bob Marley Nine Mile and Hip Strip with Shops and Dispensary

Visit the birthplace and hometown of reggae legend Bob Marley during this day trip from Montego Bay. Explore the remote village of Nine Miles, located in St. Ann parish, to see where Bob Marley was born and spent his formative years. See Mt. Zion, where Bob frequently meditated and composed music. Learn about the Rastafarian religion that the musician practiced through informative, engaging commentary from your local guide. Then stop at the ‘Hip Strip’. • Discover Nine Miles, Bob Marley's birthplace, on a tour from Montego Bay • Learn about the life and death of the Rastafarian musician • Soak up the views of the countryside and mountain peaks • Visit the ‘Hip Strip’ which offers shopping, food, drinks, gambling, and dispensaries • Round-trip transportation from Montego Bay is included
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  • 7 to 9 hours
  • Free Cancellation
From
$135.00
Price varies by group size
From
$135.00
Price varies by group size

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

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

Montego Bay highlight and Shopping from Montego Bay Hotel & Villas

Montego Bay highlight and Shopping from Montego Bay Hotel & Villas

Take a guided tour and explore the landmarks and highlights of Montego Bay and surrounding areas. Shopping at local craft market and Hip strip, enjoy local cuisines.
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  • 5 to 7 hours
  • Free Cancellation
From
$80.00
Price varies by group size
From
$80.00
Price varies by group size

Montego Bay City Tour

Montego Bay City Tour

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.
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  • 2 to 3 hours
  • Free Cancellation
From
$35.00
From
$35.00

Rehab sports bar Day or Nightlife Experience with Private Transportation

Rehab sports bar Day or Nightlife Experience with Private Transportation

This tour is Unique because Basically The tour promotes Montego Bay’s amazing Local Bars. We will visit rehab (the off the beaten path spot) You will easily get many opportunities to mingle and interact with the people of Montego Bay. This bar you visit is unique 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 at the start of the tour if you choose to book this in the evening hours. 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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  • 4 hours
  • Free Cancellation
From
$97.00
Price varies by group size
From
$97.00
Price varies by group size

Jamaican Local Restaurant and Food Tasting Tour with Private Transportation

Jamaican Local Restaurant and Food Tasting Tour with Private Transportation

Explore Montego Bay through its cuisine on this private Jamaican food-tasting tour. With a guide, taste local dishes such as brown stew fish, curry goat, and, of course, jerk chicken. Plus, stop at a fruit stand to sample fresh mangoes, coconuts, and more. Enjoy transportation by private vehicle. Private Jamaican food tour from Montego Bay Get a taste of Jamaica as you try dishes like jerk chicken, curry goat, or beef patties Enjoy fresh fruit from a side-of-the-road stand Learn about authentic Jamaican cuisine from a private guide This tour only charge for transportation so travelers will pay for their own meals.
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  • 3 to 4 hours
  • Free Cancellation
From
$130.00
Price varies by group size
From
$130.00
Price varies by group size

Rocklands Bird Sanctuary & City Highlights plus Shopping from Montego Bay

Rocklands Bird Sanctuary & City Highlights plus Shopping from Montego Bay

star-4.5
11
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

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

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

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

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

Margaritaville Hipstrip and Shopping with Private Transportation in Montego Bay

Margaritaville Hipstrip and Shopping with Private Transportation in Montego Bay

star-4
4
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

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

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. 
More
  • 6 hours
  • Free Cancellation
From
$135.00
From
$135.00

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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)?