Montego Bay Private Tour: Sam Sharpe Square & Hip Strip

Cruise Montego Bay’s lively streets and savor authentic jerk chicken flavors on your own schedule

A private 3-hour guided tour of Montego Bay departing from Falmouth, where a professional driver and tour guide picks you up from your hotel and takes you through the town's historical landmarks, including Sam Sharpe Square and the local market, then along Jimmy Cliff Boulevard to see beaches, hotels, and craft shops. The tour covers four main stops across the town and its communities, with time built in to grab local food at your own expense.

Step-by-step itinerary

Montego Bay private guided tour

• Pick up from hotel in minibus
• Visit Sam Sharpe Square for 30 minutes
• Explore local market for 30 minutes
• Tour local communities for 30 minutes
• Walk along Hip Strip/Jimmy Cliff Boulevard for 45 minutes
• View Montego Bay viewpoints for 15 minutes
• Try local cuisine at own expense for 30 minutes
• Experience local grill food preparation

The Experience

Your driver arrives in a private air-conditioned minibus and picks you up from your hotel or designated meeting point in Falmouth. From there, the route moves into Montego Bay proper, starting at Sam Sharpe Square—the historical heart of the town—where you spend 30 minutes exploring the square and its significance. The guide walks you through what the space means to the island's history and points out the surrounding architecture and layout.

Next is the local market, another 30 minutes where you see how Jamaicans shop for produce, spices, and everyday goods. Then the tour moves through local communities for 30 minutes, giving you a sense of how people actually live beyond the resort strip. The longest stop comes on Jimmy Cliff Boulevard—the hip strip—where you have 45 minutes to walk past Margaritaville, major hotels, beaches, and shops stocked with Jamaican art and crafts. This is where most travelers grab lunch on their own dime; the guide can point you toward the jerk chicken and patties the area is known for. A final 15-minute stop at a viewpoint lets you see Montego Bay from above before the drive back to your hotel.

The whole day runs three to four hours door-to-door. Because it's private, the pace and stops adjust to what you want to linger on. The guide speaks English and knows the town well enough to answer questions as you move through it.

What’s included

• Professional driver and tour guide who speaks English.
• private air-conditioned minibus transport.
• pickup and drop-off from your hotel or designated meeting point in Falmouth.
• stops at Sam Sharpe Square, the local market, local communities, Jimmy Cliff Boulevard, and a viewpoint overlooking Montego Bay.

Good to know

Easy physical levelStroller friendlyInfant seats availablePublic transport nearby

Operated by DJZ Transfer & Tours

Is this one for you?Choose this private minibus tour if you want a guide navigating you through Montego Bay's town square and communities rather than exploring independently, with the flexibility to set your own pace.

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Top questions

What is Sam Sharpe Square and why does the tour spend time there?

Sam Sharpe Square is the historical center of Montego Bay and a key landmark in Jamaica's history. The guide spends 30 minutes there walking you through the square's significance and the buildings around it, so you understand what you're looking at instead of just passing through.

Can I eat lunch during the tour, or is that on my own?

Lunch is at your own expense. The tour includes a 30-minute stop where you can grab food—jerk chicken and patties are local specialties—but you pay for it yourself. The guide can recommend spots along Jimmy Cliff Boulevard where most travelers eat.

How long is the tour and what time does it start?

The tour runs three to four hours total, including pickup and drop-off. Start time depends on your hotel location in Falmouth; the driver coordinates that when you book and picks you up from your accommodation.

Is the minibus air-conditioned?

Yes, transport is by private air-conditioned minibus, so you're not riding in heat between stops. The vehicle fits small groups comfortably and has space for luggage and strollers if you're traveling with children.

What's on Jimmy Cliff Boulevard and how much time do I have there?

Jimmy Cliff Boulevard is the main tourist and commercial strip in Montego Bay, lined with Margaritaville, major hotels, beaches, and shops selling Jamaican art and crafts. You get 45 minutes to walk around, shop, and eat—the longest single stop on the tour.

Do I need to be in good physical shape for this tour?

The tour suits all fitness levels. You're mostly walking at a comfortable pace through town squares, markets, and streets, with stops built in to rest. There's no hiking, climbing, or strenuous activity involved.