A bar tour can be more than drinking. It’s a fast way to learn the rhythm of Montego Bay, with Beanland Tours guiding you through local spots and the Hip Strip. I like how the tour mixes true hangout energy with big-name ease, and I also like the small-but-smart touch: Red Stripe is waiting at the start.

Two things I’d highlight right away: the guide Beans brings friendly local context (including his own upbringing), and the stops feel timed for real conversation instead of nonstop rushing. There’s also private round-trip transportation, so you’re not worrying about rides after a couple drinks.

One consideration: alcohol isn’t included beyond that first free beer, so your final spend will depend on what you order at each bar. Also, you must be 18+ if you want to drink alcoholic beverages.

Key Things I’d Prioritize Before You Go

• Beans as your guide: friendly, engaging, and people-friendly in the moment, not just on paper
• Free Red Stripe at the start: a quick way to get into the local groove immediately
• Three distinct stops: a local bar vibe first, then Hip Strip classics, then another bar stop to keep options open
• Pickup + private round-trip transportation: easier logistics when you’re only in town for a short stay
• 18+ drink rule: you can still join, but drinking alcohol has an age requirement

Montego Bay Bars You’ll Actually Want to Visit

Montego Bay has plenty of “look but don’t touch” tourism. This tour is the opposite. You’re going for the places where people go to watch games, chat with friends, and order something cold without making it a whole production.

I like that you start with a local bar feel and listening to the people around you. That matters because your first drink in Jamaica sets the mood. When you’re getting your bearings in a new city, a guide who knows how to talk to locals makes the difference between feeling like an outsider and feeling like you’ve joined the conversation.

Then you roll into the Hip Strip. That’s the part of town most visitors recognize, and it’s useful for a quick, low-stress taste of the more tourist-forward bar scene. The trick is balance: local energy first, Hip Strip comfort next, and another stop to round it out before you head back.

The tour is built for a short window too. It runs about 3 hours, which fits nicely when you want fun without losing your whole afternoon.

The 3-Hour Plan: What Happens at Each Stop

You’ll be moving at a pace that feels designed for hanging out, not sprinting. The schedule is tight enough to keep it fun, but not so tight that you feel trapped at the bar. Here’s how the day flows.

Stop 1: Montego Bay Local Bars to Set the Mood (1 hr 30 min)

The first stretch is all about getting that Jamaica vibe early. You’ll hit local bar stops where you can chill, drink, and listen while you “reason with locals” and build comfort fast.

Why this first stop works: your guide can put you in the right headspace before the Hip Strip. And your group gets breathing room—1 hour 30 minutes is long enough to actually talk, not just take a photo and leave.

Also, the tour starts with a free Red Stripe beer. That’s a smart move for two reasons. First, it gets the experience going immediately. Second, it’s a recognizable Jamaican beer that helps you feel like you’re not guessing at the menu.

Potential drawback here: since the focus is local hangout time, the atmosphere may be less “polished” than what some visitors expect from a resort bar. If you want a totally controlled, resort-style setting, you might find the local style a bit more casual than you’re used to.

Stop 2: Hip Strip at Margaritaville Montego Bay (30 min)

Next, you head to the Hip Strip for a classic stop at Margaritaville Montego Bay. This is the quick-hit part of the tour—30 minutes—so think of it as a vibe checkpoint rather than a long sit-down.

You’ll have time for cocktails or beers while listening to music and spotting the usual Hip Strip scene. The value here isn’t that it’s the most intimate place on earth. It’s that it’s familiar enough that you can order comfortably and still feel the energy of the area.

How to make the most of this stop: choose something you can drink easily and move with the music. Since it’s only half an hour, you’ll enjoy it more if you treat it like a short celebration rather than a long break.

Stop 3: Wings and tings Restaurant and Bar (1 hr)

The final stop brings you back to a more laid-back bar setting at Wings and tings Restaurant and Bar. You’ll get about 1 hour here, which is enough time to settle in and order based on what your group feels like.

The big perk is variety—different types of liquor are available, so you’re not stuck choosing from a narrow list. This last hour is also where I think the group usually hits its stride, because you’ve already started building rapport with your guide and your group has settled into the tour pace.

Based on what I’ve learned from how Beans runs things, this stop is the one you should use to ask questions. He’s not just driving you around—he’s engaging, and he can share context in a way that makes the bars feel like part of the city instead of just a stop on a checklist.

Why the Guide Makes This Worth $85

Let’s talk about the real value driver here: the human factor. Tours like this can turn into a ride plus a to-do list. This one seems designed to avoid that, largely because the guide matters.

The guide’s name is Beans, and the most positive comments tie directly to his personality and attention. People describe him as friendly and engaging, and they specifically mention him being knowledgeable in the way that helps you understand what you’re seeing. One review also highlighted that he helped make the moment social—someone even connected with a new friend at a sports bar thanks to his approach.

Another strong theme: he shares history and personal context, including his own upbringing. That kind of story doesn’t just entertain. It changes how you hear music, how you interpret local conversation, and how you experience the spaces you’re in.

If you’re wondering whether a bar tour needs a guide, here’s my take: you’re paying for time, transport, and a smoother social setup. In a place like Montego Bay, that’s not a small thing. Without a guide, you might stumble into random bars. With one like Beans, you’re guided toward the spots where the group vibe makes sense.

What’s Included vs What You’ll Pay for On Your Own

This is one of those tours where the value is clear if you separate included pieces from optional spend.

Included:

• Free Red Stripe beer at the start
• Private round trip transportation (pickup is offered)
• You’re on a private tour for your group

Not included:

• Alcoholic beverages (after that first free beer, you’ll be buying your own drinks)
• Lunch

So the $85 price is paying mostly for logistics and guidance. That can be a good deal if you plan to drink at multiple stops anyway. If you’re the type who wants one drink and calls it a night, you might feel like the alcohol budget isn’t automatically built in.

My practical advice: think of the included beer as your kickoff. Then set a rough drink plan for the rest of the evening. That way, the “not included” part doesn’t surprise you.

Pickup, Group Discounts, and the Practical Stuff That Saves Time

You’re offered pickup, and there’s private round trip transportation. That means fewer taxi decisions, fewer route worries, and less time figuring out how to get back after your final stop.

The tour also notes group discounts. If you’re traveling with friends, that’s where your per-person value can improve. Even if you don’t get a big discount, the private setup helps keep the experience focused on your group instead of mixing everyone into one chaotic cluster.

A small detail that matters: the tour uses a mobile ticket. That’s handy when you’re bouncing around on vacation and don’t want paperwork clutter.

One more practical note: it says you’ll be near public transportation. I’m not suggesting you plan to use it, but it can reassure you that the area isn’t isolated if you need options.

Who This Tour Fits Best

This one matches best with travelers who want fun that still feels tied to the city.

You’ll likely enjoy this if:

• You want a short, structured bar experience (about 3 hours)
• You like social travel, music, and people-watching
• You prefer having a guide handle timing and movement
• You’re okay paying for drinks at stops (beyond the first included beer)

It may not be your best match if:

• You want all-inclusive alcohol
• You dislike casual local settings and want only resort-style bars
• You’re visiting with zero flexibility for weather, since the experience requires good weather

Weather and Timing: Simple Planning That Prevents Stress

This experience requires good weather. That means rain or poor conditions can affect whether it runs that day.

The timing length is also a big clue for expectations. At around 3 hours, you won’t leave feeling like you “saw the whole city.” You’ll leave feeling like you got a smart sample of bar culture and a head start on understanding Montego Bay’s mood.

One last timing note: on average, this gets booked about 66 days in advance. If you’re traveling during a busy period, I’d book early rather than gambling on last-minute availability.

The Real Takeaway: What You’ll Leave With

If you do this tour, you’ll leave with more than a drink receipt and a couple photos. You’ll have a few hours where:

• You try a Jamaican classic right away with the free Red Stripe beer
• You get time to relax in local bars before switching to Hip Strip energy
• You finish with a final bar stop that still gives you breathing room
• You get conversation and context from Beans, including personal stories and explanations that make the stops feel connected

That’s the heart of it: you don’t just visit bars. You’re guided through how people hang out.

Should You Book This Montego Bay Bar Hopping Tour?

Book it if you want an efficient, friendly way to experience Montego Bay nightlife without heavy planning. The included transportation and the guided pacing are what make it feel like good value, especially if your group is aiming for multiple drinks across a couple areas.

Skip it (or rethink it) if you want an alcohol-inclusive package, or if you’d rather explore on your own with zero guide time. Also, if you’re sensitive to casual local atmospheres, the first stop may feel more down-to-earth than you’re expecting.

If you’re still on the fence, here’s my simple checklist: you should book if you’re happy spending on drinks at the bars, you can go with the weather, and you want a guide like Beans who helps you connect to the scene instead of just passing through it.

FAQ

Is pickup included on the bar hopping tour?

Yes. Pickup is offered, and private round trip transportation is included.

How long is the tour?

It’s about 3 hours.

How much does the tour cost?

The price is $85.00 per person.

What bars or locations do you visit?

You visit local bar stops in Montego Bay, then Margaritaville Montego Bay on the Hip Strip, and then Wings and tings Restaurant and Bar on the Hip Strip.

Is Red Stripe included?

Yes. You get free Red Stripe beer at the start of the tour.

Are drinks included?

Alcoholic beverages are not included. Only the initial Red Stripe beer is included.

Do you have to be 18 years old?

Yes, you must be 18 years or older to drink alcoholic beverages.

Is this a private tour?

Yes. It’s private, and only your group participates.

What happens if the weather is bad?

The experience requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.

Can I cancel for free?

Yes. Free cancellation is available up to 24 hours in advance for a full refund. Within 24 hours, refunds are not available.