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Hip Strip (Gloucester Avenue) Tours and Activities

Hip Strip (Gloucester Avenue)
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.

The Basics
As the main hub of tourist activity in Montego Bay, expect jubilant crowds, thumping reggae music, free-flowing rum drinks and Red Stripe, and shopping galore, from high-end duty-free boutiques to trinket stalls. A popular destination is Jimmy Buffett’s Margaritaville, a double-decker bar with giant water trampolines and a 120-foot (37-meter) water-slide that plunges into the warm waters of the Caribbean. The Strip’s best bet for live music (and martinis) is the Blue Beat Jazz Lounge, where revelers have a romantic view of the sea.

Travelers have many options to experience the Hip Strip as part of half-day, full-day, group, or private tours that may incorporate a visit to Rocklands Bird Sanctuary, a local artisan market, a nearby beach like Doctor’s Cave or Agua Bay, or a place to admire a panoramic view of Montego Bay. Other tours may include a Jamaican meal at a local restaurant. 

Things to Know Before You Go
  • The Hip Strip is ideal for party-goers visiting Montego Bay. It’s a lively area, so it might not be suitable for those looking for a mellow, off-the-beaten-track experience or for small children.
  • With so many shops selling similar souvenirs and t-shirts, feel free to gently haggle for better prices.
  • Along the Hip Strip are access points to popular beaches like Cornwall or Doctor’s Cave. Some beaches have small admission fees that would be included if visiting as part of a tour. 
  • While safer than the downtown area of Montego Bay, use your discretion and stay in the more populated areas, especially at night.

How to Get There
Montego Bay’s Hip Strip runs along Gloucester Avenue, from Aquasol Theme Park to Sangster International Airport. It is walking distance or a quick taxi ride from many nearby hotels (some of which offer free shuttles).

When to Get There
A hot spot day and night, the best time to visit the Hip Strip depends on whether you want to incorporate a stop at the beach or a night out on the town. The warm months of winter comprise the busiest time of the year.

Treasure Hunters Welcome
One of the best-reviewed Hip Strip souvenir shops is Tropical Treasures, where owner Sammie makes you feel at home—and has even been known to give discounts for smiling. Travelers say the prices here are fair and that his no-hassle attitude is a welcome pleasure. 

Address: Gloucester Ave, Montego Bay, Jamaica
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25 Tours and Activities to Experience Hip Strip (Gloucester Avenue)

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Montego Bay Half-Day Shopping Tour

Montego Bay Half-Day Shopping Tour

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26
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
  • Taking safety measures
From
$10.00
From
$10.00
Taking safety measures

Doctor's Cave Beach Day-Trip with Jimmy Buffett's Margaritaville & Shopping

Doctor's Cave Beach Day-Trip with Jimmy Buffett's Margaritaville & Shopping

star-4.5
7
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
  • Taking safety measures
From
$46.16
Price varies by group size
From
$46.16
Price varies by group size
Taking safety measures

Rocklands Bird Sanctuary & City Highlights plus Shopping from Montego Bay

Rocklands Bird Sanctuary & City Highlights plus Shopping from Montego Bay

star-4
9
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
  • Taking safety measures
From
$109.99
From
$109.99
Taking safety measures

Montego Bay Highlight Tour Visit local Community And See Local Stuffs

Montego Bay Highlight Tour Visit local Community And See Local Stuffs

star-4.5
3
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

Private Montego Bay Highlights Tour

Private Montego Bay Highlights Tour

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5
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
  • Taking safety measures
From
$54.49
From
$54.49
Taking safety measures

4 Hours Montego Bay Private Sightseeing Highlight Tour

4 Hours Montego Bay Private Sightseeing Highlight Tour

Explore Montego bay, Jamaica on This Four (4) Hours Sightseeing Tour with a private driver and van for your Exclusive Group which you can . The vans can hold a capacity of up to 10 persons and picks you up from your Montego bay Resorts Hotels and Villas  . See all the interesting Sights of Montego Bay . See local Communities where native live  so you can feel immersed in the Jamaica  way of life . No need to just sit in your resort and the say you visited jamaica we provide a safe tour for you and the family
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  • 4 hours
  • Taking safety measures
From
$307.70
per group
From
$307.70
per group
Taking safety measures

Montego Bay Fast Track Sightseeing Plus Parasailing

Montego Bay Fast Track Sightseeing Plus Parasailing

Montego Bay Fast Track Sightseeing private tour plus parasail tour combo experience in the city of Montego Bay Jamaica. Explore the city's local area of Hip Strip ,Elegant Corridor , Sam Sharpe Square  ,See local communities where natives live and entertain. After a Fast Track Sightseeing Tour enjoy a visitor favorite water sports activity Parasailing Tour . This is quick sightseeing tour combo with Parasailing Tour in Montego Bay Jamaica.
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  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$192.31
Price varies by group size
From
$192.31
Price varies by group size
Taking safety measures

Private Tour of Montego Bay: Includes Sightseeing

Private Tour of Montego Bay: Includes Sightseeing

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1
Experience Jamaica away from the tourist crowds on this private half-day tour of Montego Bay. Head to less-visited landmarks such as St James Parish Church, Richmond Hill Great House, and Sam Sharp Square, and explore the surrounding countryside to see villages and farms that grow sugarcane, cacao, and tropical fruits. You can also taste authentic Jamaican dishes during a lunch stop (own expense) at a popular local restaurant.
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  • 3 hours
  • Free Cancellation
From
$61.54
Price varies by group size
From
$61.54
Price varies by group size

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

Day Trip: 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
  • Taking safety measures
From
$69.50
From
$69.50
Taking safety measures

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
  • Taking safety measures
From
$116.99
From
$116.99
Taking safety measures

(MBJ) Montego Bay Highlight Tour

(MBJ) Montego Bay Highlight Tour

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3
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. Fun Trip Jamaica guarantees all the other attractions, food ad highlights will only enhance your love of Jamaica.
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  • 1 to 4 hours
  • Free Cancellation
  • Taking safety measures
From
$46.16
From
$46.16
Taking safety measures

 5-Day Mini-Vacation Package at Holiday Inn Montego Bay, Jamaica

5-Day Mini-Vacation Package at Holiday Inn Montego Bay, Jamaica

Best Vacation Ever! 5 Days/4 Nights All-Inclusive Accommodation at a Montego Bay Family Resort with Family Morning Catamaran Cruise and Snorkeling Experience.
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  • 5 days
  • Taking safety measures
From
$769.24
From
$769.24
Taking safety measures

5-Day Mini-Vacation Package at Royal Decameron Montego Bay, Jamaica

5-Day Mini-Vacation Package at Royal Decameron Montego Bay, Jamaica

Best Vacation Ever! 5 Days/4 Nights All-Inclusive Accommodation at a Montego Bay Family Resort with Family Morning or Adults Only Afternoon Catamaran Cruise and Snorkeling Experience.
More
  • 5 days
  • Taking safety measures
From
$615.39
From
$615.39
Taking safety measures

5-Day Luxury Mini-Vacation Package at Secrets Wild Orchid Montego Bay, Jamaica

5-Day Luxury Mini-Vacation Package at Secrets Wild Orchid Montego Bay, Jamaica

Best Vacation Ever! 5 Days/4 Nights Luxury All-Inclusive Accommodation at a Montego Bay Adults Only Resort with Afternoon Catamaran Party Cruise and Snorkeling Experience.
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  • 5 days
  • Taking safety measures
From
$1,948.72
From
$1,948.72
Taking safety measures

5-Day Mini-Vacation Package at Jewel Grande Montego Bay, Jamaica

5-Day Mini-Vacation Package at Jewel Grande Montego Bay, Jamaica

Best Vacation Ever! 5 Days/4 Nights All-Inclusive Accommodation at a Montego Bay Family Resort with Family Morning Catamaran Cruise and Snorkeling Experience.
More
  • 5 days
  • Taking safety measures
From
$961.54
From
$961.54
Taking safety measures

Montego Bay Shore Excursion: ROSEHALL GREAT HOUSE, DOCTORS CAVE BEACH & HILITE

Montego Bay Shore Excursion: ROSEHALL GREAT HOUSE, DOCTORS CAVE BEACH & HILITE

This half-day tour really packs it in. First, visit the Rose Hall Great House, which was featured on the show “Ghost Adventures” for its White Witch legend. Drive through wealthy residential areas, through downtown, and past the “Hip Strip” area, stopping for photos and a bit of shopping along the way. The day ends with free time to swim, relax, and unwind at Doctor's Cave Beach.
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  • 4 hours
  • Free Cancellation
From
$76.93
From
$76.93

Dispensary Tour(Bundle) Montego Bay

Dispensary Tour(Bundle) Montego Bay

With This Product, you get to experience the city of Montego Bay while having the best herds at your fingertips. This is a private tour where safety is our responsibility, we sure 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. Must be in a hotel in the Montego Bay Area.
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  • 5 hours
  • Free Cancellation
  • Taking safety measures
From
$82.06
From
$82.06
Taking safety measures

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

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

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
  • Taking safety measures
From
$56.42
Price varies by group size
From
$56.42
Price varies by group size
Taking safety measures

Montego Bay Private Shopping Tour with Hotel Pickup

Montego Bay Private Shopping Tour with Hotel Pickup

star-5
1
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
  • Taking safety measures
From
$21.54
Price varies by group size
From
$21.54
Price varies by group size
Taking safety measures

Private Day Tour from Montego Bay to Negril

Private Day Tour from Montego Bay to Negril

It’s a private and customize tour that offer comfort and safety at the cheapest rate. That will blow your mind away. Our private and customize tours is to educate you about Jamaica. We Sightseeing along the way and stop at different historical sight, we also stop for you to shop if requested. We also educate about our unique fruits and trees that we have here in Jamaica while we checkout our Landscape/Architecture as we drive though different towns and village. Up reaching our Negril destination/seven mile beach. We stop on the seven mile beach for 2 to 3 hours then go to Ricks Cafe to watch the sunset goes down. Then head back to Montego Bay after the sunset.
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  • 7 to 8 hours
  • Free Cancellation
  • Taking safety measures
From
$68.00
From
$68.00
Taking safety measures

Montego Bay Highlights - Full Day Tour

Montego Bay Highlights - Full Day Tour

Your adventure includes a City Tour of Montego Bay where we will drive through the bustling downtown area. This tour will take you to the Richmond Hill area which gives a panoramic view of Montego Bay. During this amazing city tour, you will see all the most popular sights and experience the best parts of the city with a local guide. Here you can capture amazing photos of Montego Bay and its surrounding areas. We will also show you the special things that make Montego Bay great. Explore Sam Sharpe Square and visit the world-renowned Doctors Cave Beach and be entertained at the popular Jimmy Buffets Margaritaville. You may shop for sourvineers and memobars
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  • 5 to 7 hours
  • Free Cancellation
  • Taking safety measures
From
$75.00
Price varies by group size
From
$75.00
Price varies by group size
Taking safety measures

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 hours
  • Free Cancellation
  • Taking safety measures
From
$66.67
From
$66.67
Taking safety measures

Private and Customized Montego Bay Day Tour

Private and Customized Montego Bay Day Tour

star-5
112
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.
More
  • 3 to 4 hours
  • Free Cancellation
  • Taking safety measures
From
$51.29
From
$51.29
Taking safety measures

Lets do Shopping & Margaritaville in Montego Bay (Private Tour)

Lets do Shopping & Margaritaville in Montego Bay (Private Tour)

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!!
More
  • 1 to 6 hours
  • Free Cancellation
From
$84.11
Price varies by group size
From
$84.11
Price varies by group size

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)?