Three hours can feel like a whole evening. This private bar-hopping tour in Montego Bay mixes local hangouts with a couple of well-known Hip Strip stops, so you get both the street-level vibe and the easy-to-find classics. I especially like that you start with a free Red Stripe Beer, and I also like the guide style—Bean is described as friendly, engaging, and quick to help your group feel comfortable.

The main thing to consider is simple: alcoholic drinks are not included, so plan to budget extra for what you actually order.

Key points before you go

• Free Red Stripe at the start so you’re not stuck figuring out your first drink right away
• Private round-trip transportation helps keep the timing smooth across multiple bar stops
• Three timed stops (1h30, 30m, 1h) gives structure without turning it into a rush job
• Hip Strip mix includes Margaritaville Montego Bay plus another bar on the same area
• Bean’s personality matters: reviews highlight his history-sharing and upbeat group energy
• Adult drinking rules: you need to be 18+ to drink alcoholic beverages

How this bar-hopping tour really plays in Montego Bay

Montego Bay has two faces you’ll feel fast. There’s the part most visitors hit in short bursts—quick photos, quick stops. Then there’s the longer, relaxed bar rhythm locals stick with. This tour is designed to help you catch that second face without you having to plan every move.

The structure is the big win: you’re out about 3 hours, and the day is split into three bar stops with set time blocks. That means you’re not guessing when to move on, and you’re not stuck spending the whole evening at a single place just because it felt easiest. It also helps if your group has different comfort levels—some people want lively music, others just want good company and a cold drink.

And the “private tour” part isn’t just marketing fluff. In the reviews, the experience centers on Bean working with your group, keeping things on time, and making it feel like a shared night out rather than a conveyor belt. In other words, you get pacing plus personality.

What $85 buys you (and where you’ll spend more)

At $85 per person for about 3 hours, the value is mainly in the logistics and the starting drink. You get:

• Pickup offered (private round-trip transportation)
• A free Red Stripe Beer at the start of the tour
• A plan with three stops, each with its own vibe

What you should expect to pay for separately:

• Alcoholic beverages (not included)
• Lunch (not included)

That trade-off matters because you can control the spend. If you’re the type who wants just one or two drinks, this is usually a comfortable way to try a few places without a huge bar tab. If you’re going hard, you’ll want to budget like you would for a normal night out—this tour doesn’t cover your orders after that starter beer.

A smart approach: decide in advance how many paid drinks you want, and keep that number in mind once you’re on the Hip Strip. It’s easy for a bar night to drift when the music is good and the group energy picks up.

Stop 1: Montego Bay local bar time (1 hour 30 minutes)

This is where the tour starts building the right kind of mood. The first stop is described as local bar stops where you chill, drink, listen to music, and talk with locals. It’s intentionally not framed as a tourist-only stop. You’re there to settle into the city’s pace before the tour moves you toward bigger-name places.

Why this stop matters: it’s the tone-setter. If you start with a low-key local bar, the later stops feel more like a progression instead of a series of random drop-offs. It also gives you a chance to learn what people actually talk about—something the guide can shape with stories and context.

One more practical thing: since this is the longest stop (1h30), you’ll likely get the best chance to try your first drink, check the vibe, and ask questions without feeling rushed.

The main consideration is that this part of the night is the most dependent on comfort with the environment—music, crowd energy, and conversation levels. If your group prefers very quiet places, you’ll want to set expectations early that this is meant to feel like a real bar hangout.

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

Next up is the Hip Strip, with a short visit at Margaritaville Montego Bay. This is the “get the familiar vibe” stop—cocktails or beers while music plays and you mix with the people out for an evening.

Why this stop makes sense: after your local bar intro, this is a quick bridge into something more recognizable. It’s helpful if your group wants a lively, easy setting where you can order without decoding a new place from scratch.

Because it’s only 30 minutes, you’re not meant to fully “camp” here. Think of it as a quick hit of Hip Strip energy—good for photos, people-watching, and resetting before the final bar.

A note on timing: short stops can feel a little intense if your group likes long conversations. Still, if you’re okay with a quick change of scenery, 30 minutes is exactly enough to sample the mood without losing the rest of the evening.

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

The last stop is at Wings and tings Restaurant and Bar, built for a chill vibe with different types of liquor available. This is where the tour tends to feel like it’s winding down in a good way: a place to linger a bit longer than the Hip Strip sprint, but still close enough to wrap the night cleanly.

Why it works as a finale: by the third stop, you usually have the hang of the group flow—who’s ready for another round, who wants to keep it light, and who just wants good conversation. This bar’s description points toward that relaxed pace, not a frantic end-of-night club scene.

If you like variety, this is your place to shift gears from beer and cocktails into something different, since liquor options are explicitly part of the plan.

The trade-off: since alcohol isn’t included, this last stop can be where the final spend adds up fastest. If you’re trying to keep costs predictable, choose what you want early—before the music and the group talk make it harder to think like a budget spreadsheet.

Beanland Tours and the guide effect (Beans/Bean)

A bar-hopping tour lives and dies by the guide, and the reviews put Bean right at the center of the experience.

The most repeated praise is how friendly and engaging Bean comes across. One review highlights Beans helping someone make a new friend at a sports bar, which tells me he’s good at reading the room and encouraging natural interactions instead of forcing awkward small talk. Another review calls him amazing and says he kept things timely, with drinks that felt great across the stops.

Then there’s the “beyond the bars” element: Bean also shares history about Jamaica and personal details about his upbringing. That’s valuable because it changes the tour from pure consumption into a shared story. You get to connect what you’re seeing—local spots, Hip Strip energy, neighborhood vibe—to something human.

And if your group is celebrating something, the vibe is supportive. One review mentions a birthday moment in the group experience, and the tone suggests Bean helps make it feel special without turning it into a production.

Pickup, private transport, and keeping the night on track

Practical transport might not sound exciting, but for a bar tour it’s everything. You’re paying for private round-trip transportation, and that does two big things for you:

1) It reduces stress. You don’t have to coordinate rides back while you’re already feeling social.

2) It protects timing. When you’ve got three stops, missing a window can throw off the whole evening.

The tour also offers pickup, and the site notes that it’s near public transportation, which can be useful if your plans change.

One more small detail that helps: confirmation is received at booking, and the tour uses a mobile ticket. That’s one less thing to manage while you’re on vacation.

Who this tour suits best (and who should think twice)

This is a strong match if you want:

• A fun adults-only bar night (18+ for alcohol)
• A simple plan with three stops and a guide to handle the flow
• A night that mixes local vibe with well-known Hip Strip energy
• A group situation where you’d like someone like Bean to keep things moving and social

It may not be your best choice if:

• You want a mostly quiet, low-key evening with minimal noise and crowd energy.
• You’re trying to do this while keeping every expense included. Drinks and lunch aren’t covered, so you’ll still be ordering pay-as-you-go.

Smart ways to get the most from the three-stop format

If you want this tour to feel effortless, here’s how I’d play it:

• Start with water between stops. You’re drinking, plus you’re out for a few hours. A quick reset helps you enjoy the whole route.
• Use the first stop to ask questions. Bean’s Jamaica history and personal stories come through in the reviews, and you’ll likely get more out of them early, when your group is freshest.
• Choose your Hip Strip goal. Since Margaritaville is only 30 minutes, decide if you want cocktails, beer, or just the atmosphere. That keeps you from feeling torn.
• Treat the last bar as your budget reality check. The third stop is a one-hour hang, and that’s when paid drinks tend to catch up with the group.
• Keep it group-friendly. This is private for your group only, so you’ll feel the energy more strongly. If your group is chatty and open, Bean can really turn that into a memorable night.

Weather and schedule fit

This experience requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund. For a bar-hopping plan, that’s worth respecting—bad weather can change how people move around the city, and it can affect the whole bar vibe.

In practice, I’d treat the tour as something to lock in early in your schedule, or at least ensure you have a flexible evening nearby in case you need to reschedule.

Should you book this Montego Bay bar-hopping tour?

If you’re looking for a straightforward, social way to see more of Montego Bay than just quick tourist stops, I think this tour is a good call. The strongest reasons are the combination of private transport, a free Red Stripe to start, and Bean’s track record of keeping the vibe friendly, timely, and story-filled.

Book it if your group wants an evening that feels like a local night out with a guide who actually adds value—not just someone driving you to bars. I’d skip it only if you’re trying to keep alcohol costs fully covered or you hate music/crowd energy.

If you do book, message ahead about your group’s vibe (chill versus lively) and set expectations about drink spending. Then show up ready to talk, listen, and let Bean steer the night.

FAQ

How long is the bar-hopping tour?

It’s about 3 hours in total.

Where does the tour run?

The tour takes place in Montego Bay, Jamaica, with stops including areas like the Hip Strip.

What is the price per person?

The price is $85.00 per person.

Is pickup included?

Yes. Pickup is offered, and the tour includes private round-trip transportation.

What is included in the tour price?

The tour includes a free Red Stripe Beer at the start of the tour.

Are alcoholic drinks included?

No. Alcoholic beverages are not included in the tour price.

What are the age requirements for drinking?

You must be 18 years or older to drink alcoholic beverages. Drink responsibly.

How many stops are there?

There are three stops: a local bar in Montego Bay (1h30), a Margaritaville Montego Bay stop on the Hip Strip (30m), and Wings and tings Restaurant and Bar (1h).

What happens if the weather is bad?

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

What is the cancellation policy?

Free cancellation is available up to 24 hours in advance for a full refund. If you cancel less than 24 hours before the start time, the amount paid is not refunded.