How to spend two weeks in Jamaica

by Sofia
Published: Updated:
Palm trees and blue skies on Jamaica's Negril beach

With an abundance of Virgin Atlantic air miles and a couple of expiring companion vouchers burning holes in our pockets, Sam and I booked a two-week trip to Jamaica. The original plan was to fly into Montego Bay for the beaches, drive across the country, and fly out of Kingston. However Virgin Atlantic do not offer direct flights to or from Kingston. Instead we opted for round-trip flights to Montego Bay. Our thinking was we would spend our last three nights in Jamaica in Kingston and transfer there and back via taxi.

Blue skies, mountains, and forest in Jamaica

A new plan: How to spend two weeks in West Jamaica

If you look at a map of Jamaica, it isn’t that big. At 11,000 km2 it is still the 3rd largest island in the Caribbean, but nothing seemed far. We had to go to the best area in the country for beaches for at least part of our trip. This was as west as you can go in Jamaica. Negril is world famous for its Seven Mile beach.

Sitting at Alfred's bar at the weekend in Negril, Jamaica
Sitting at Alfred’s on Seven Mile Beach

When we looked into booking taxis on Gettransfer, as we always do in place of renting a car, the pricing was surprisingly prohibitive. We also heard from local taxi drivers that the drive times in Jamaica were longer than Google Maps advertised. Buses were an affordable albeit painful six-hour option. This was no way to spend six hours of our two weeks in Jamaica.

Mangroves on Black River in Jamaica
Black River

Long story short, we decided against spending a small fortune and significant amount of time on our trip in a car. Instead decided to do a full week of our trip to Jamaica in Negril, followed by tours of the west and south of the island. 

Wedding on the beach at Sandals Jamaica

This trip started with a couple of our Caribbean traditions. Traditions which began with our eye-opening trip to Barbados in December 2020, with a certain brand of resorts perceived to be tacky by the discerning millennial explorer.

How to start two weeks in Jamaica… Sandals!

This first tradition was a four-night stay in Sandals Negril. While you might feel a bit trashy at first, just embrace it. Enjoy being relaxed (and sauced) to the max while you’re at a Sandals.

A Sandals diving boat anchored on Negril Beach in Jamaica

Just don’t make it the entirety of your trip or you’ll end up losing value staying at an all-inclusive when your body pleads for reprieve. Worse still you won’t explore any of the island that you just travelled so far to see, nor experience the full depth of its culture. But still, before all that, why not start with a bang?

For our Jamaica trip in particular, Sandals was a great place to start, as they always include airport transfers to their resorts. Negril is a good 90-minute and £70 transfer from Montego Bay Airport so we were making savings right away! To make this drive slightly more palatable after a 10-hour flight, Sandals have a welcome lounge at Montego Bay Airport. There were drinks on tap and snacks while we waited 15 minutes for our driver. We changed in their private bathrooms.

A waterbird walking towards the camera at the beach in Jamaica

Sandals Negril

This Sandals (there are 7 in Jamaica!) was by far the smallest we’d been to, with only 400 or so guests. It was quiet and whilst the trash factor was still high (think three-layer-frozen-cocktails that take 10 minutes to make for the portly patron while you’re just waiting on a can of Red Stripe), it was a pretty chilled-out place to spend a few days.

Swim-up bar at sunset at Sandals in Jamaica

I went for a scuba dive, a (failed) private water-ski lesson, a subsequent successful kneeboarding lesson, and many tubing rides between drinks on the beach. The food was good without being amazing. We enjoyed Jamaican patties on the beach and jerk chicken poolside.

Jerk chicken and rum punch on the beach in Jamaica

We will probably never start a trip to a Caribbean island with a Sandals without a trip to said Sandals for an all-inclusive blast.

Fire show on the beach in Jamaica

No plans, and no plans to plan

Our second Caribbean tradition is planning absolutely nothing for after our Sandals reservation. On our Barbados 2020 trip, this was reasonable. We didn’t want to commit to anything in case we ended up in Covid jail. See our previous Barbados post for context. There was also no shortage of inexpensive hotel rooms at the height of Covid restrictions, so it was easy to walk next door to a hotel after we left Sandals. In Antigua in April 2022, it was less reasonable. Then I was holding out hope that we might get an additional few nights added to our Sandals stay free of charge simply because that’s what happened in Barbados.

This time, for our two-week trip in Jamaica, the lack of forward planning was both reasonable and stupid. None of the hotels on the Negril strip where we wanted to stay afterwards had websites or even phone numbers. I thought we could just walk over one morning to make a booking at our favourite place and negotiate a last-minute deal in person. We had also been approached by several tour guides in our previous two Sandals trips trying to sell us various day trips on the beach. So again, we figured the same would happen again and the whole plan would just fall into our laps. This did not happen. But with a couple of mornings spent planning on our phones on the beach with pineapple mimosas in hand, we figured it out. 

Negril Beach

Tamboo Resort hotel on Negril beach in Jamaica

We opted out of the free transfer back to the airport, and instead booked our own taxi to Tamboo Negril. It was about a 10-minute drive south at the other end of the Seven Mile Beach. The hotel rooms were, shall we say, basic to the point of leaking in the rain. But the hotel reception were beyond friendly and helpful in booking this taxi for us and adding it to our room rate. We checked in as late as we could so we could max out our last night at the open bar at Sandals. The hotel staff were kind enough to let us pay the next morning. It was £293 for four nights including the taxi ride. That’s less than the cost of one night at Sandals Negril.

We arrived to a bonfire on the beach and had one last Red Stripe (500 JMD / £2.73 per 341ml bottle) before going to bed.

A bonfire at night on Negril Beach in Jamaica

So began the second chapter of our trip: the real-life Jamaica.

Cash Problems

Leaving the all-inclusive Sandals in a hazy stupor, we were faced with our first real-life challenge. We had $26 in USD cash and zero in $JMD. It was tourist Negril, so surely most places would take card, right? Wrong. Most places on the beach were still cash only. We walked to the two ATMs across the street. One was empty, and the other said that it wouldn’t accept our cards. Typically we use Curve cards to withdraw cash on foreign ATMs as there are no withdrawal fees besides what the ATM charges, as well as a £200 monthly allowance of zero FOREX fees to boot. We had become so complacent and reliant on withdrawing cash upon arriving rather than in advance that neither of us even thought to bring our actual debit cards to Jamaica. Idiots.

Catamaran at sea

Obligatory Catamaran Cruise

Fortunately, we had a catamaran cruise pre-booked on Viator for that afternoon. This cost us £35 each, down from £70 thanks to double dipping on a Quidco and Amex offer. The $26 covered our lunch at an oil drum jerk grill on the side of the road ($8 per quarter jerk chicken with a slice of bread), and a couple of beers. The starting point for the catamaran cruise happened to have a functional bank ATM across the street.

Boats in blue watered bay in Jamaica

Thankfully it worked out, but we really should have turned up with some cash ready to go. US dollars are widely accepted. Many places in Negril which accepted card would only allow a charge in USD, and every place seemed to go by their own exchange rate of JMD or USD. In every instance but one it was favourable to pay in JMD over USD, often knocking a whopping 20% or 30% from the price.

Back to the catamaran cruise. I am not actually a boat person, but often when Sam and I travel somewhere with miles of beautiful coastline, we take a catamaran cruise. This one left from Margaritaville on Negril beach (more on this later) down the coast to Rick’s Cafe and back up during sunset. This included rum punches and beers. Sounded like a lovely afternoon in Jamaica.

We were among the last on the boat (my fault, I wanted to run across the street to withdraw cash (and failed)). It shocked me to see a good 100 people on the boat. This included one birthday party and two bachelorette parties. Not exactly relaxing, or comfortable for that matter. The boat was rammed. No lying on the deck to get sun on this excursion! 

Rick’s Cafe

The way out was a bit rough and we had clouds. I was grumpy at my poor decision for our afternoon plan. Once we got off the boat at Rick’s, I perked back up. Overlooking the cliff edge bar to the cliff divers across the way, we had a couple of Red Stripes (£5, which would have been much less had we had JMD to pay in). Rick’s is one of the most famous bars in all of Jamaica because it has cliffs that patrons and professionals can dive from in between drinks. What could go wrong! As with all famous tourist spots with food and drink, expect to pay a premium. And don’t bother with the food.

Cliff divers at Ricks Cafe in Jamaica

The ride home was much nicer, and our very poor spots in the corner on the way in became the most desirable seats in the house on the way home. We watched the coast and the sunset on the way back. Poetic.

Sunset over the sea in Jamaica

The boat docked back in Margaritaville. Margaritaville is the ultimate trashy bar chain in Jamaica. The food looks horrendous and the drinks are the same price as you should expect to pay in London. This was by far the most expensive we saw in Jamaica. Forgo the one on Negril Beach and go to literally any other bar for a nicer time at half the price.

Negril’s Local Spots

Back on dry land we finally found a working ATM and withdrew as much cash as we could. Tip: the NPC machine capped us at 30k JMD per withdrawal for a fee of £3. We walked back down the street towards our hotel. We had a good dinner en route at Best in the West, which a local employee at Sandals had recommended to us. 

Best In The West

Negril Breakfasts

The remaining few days on the beach of Negril were so chill. We would go for breakfast nearby. Once at Alfred’s on the beach, once at Cafe Goa across from our hotel, and twice at Blue Mountain Coffee.

Traditional Jamaican breakfast Alfred’s

After breakfast, we would pick up our beers for the day at a shop across the street from the beach. At the shop the Red Stripes were only 260 JMD vs 500 JMD on the beach. We would load them into our fridge to drink later in the day. The joys of a beachside hotel.

Blue Mountain Coffee Shop

The mornings in Negril were always beautiful, hot and sunny, and we spent them on the beach. Beach vendors would come by selling fresh fruit, fresh juice, patties, and of course, weed. Every hotel had its own little beach setup complete with chilled-out music, lounge chairs, and a bar.

A beach bar in Jamaica
Looking out to see from a Jamaican beach bar
Licence plates and bottles of spirits at a Jamaican beach hut

Negril Jerk Spots

The early afternoons tended to get cloudier and there was usually a bit of rain for an hour or two. At this point, we would go get some roadside jerk.

Rum punches in plastic cups on the beach in Jamaica

The first road in from the beach running north to south of the seven-mile strip, Norman Manley Blvd, was home to local restaurants and BBQ steel drums turning out roadside jerk chicken. One afternoon we went to Smokey Joe’s. This was a bit of a crossover between a restaurant and a stall as he had a place to sit and he served drinks.

Smokey Joe’s

Another afternoon we went to Sauce Daddy who was just outside our hotel. This was so delicious and he even gave us a bottle of his jerk to take away. We preferred the chicken at Sauce Daddy. This was half the price even with our sauce souvenir.

Sauce Daddy

Negril Dinner Spots

The second Norman Manley Blvd meal we got was at Sweet Spot, another recommendation from a local. This was very casual. Food was served in styrofoam as if for takeaway – but it was delicious and so fun. We ordered three meals to share between us.

Sweet Spot

For our third dinner, we walked up the sandy strip to the other end of the beach to Fireman’s Lobster Pit. We had spotted this place while we were at Sandals, which is right next door. Of course, we couldn’t eat out during our all-inclusive binge.

Fireman’s Lobster Pit is a small wooden cabin right on the beach with a room dedicated to an open coal pit upon which they cook the food. We sat overlooking the water and watched the sunset over their pen of ultra-fresh lobsters. Forget a fresh tank. This was literally a giant cage of lobsters free to swim within its confines in the ocean. We watched the grillmaster pick one out for us. For $35 USD you got a lobster with two sides.

Fireman’s Lobster Pit

All along Norman Manley Blvd, there are ‘route taxis’ shuttling back and forth from one end of Negril to the other. We had bar-hopped by foot along the beach up to Fireman’s Lobster Pit, but we weren’t keen on the 30-minute walk back in the dark. So we took our first route taxi.

Jamaican Route Taxis

Route taxis are the licensed taxis of Jamaica, they must have a red license plate. You should never get in a taxi without one! But they are only licensed to go along a specific route, thus the name. They are shared, a bit like a bus is, but it’s just a car. They come by about every 30 seconds, too. A bit hesitant, we flagged one down. We paid our $130 JMD / less than £1 each and got dropped off exactly where we wanted. The taxi dropped off and picked up one other person along the way. It is good manners for tourists to tip for longer rides or if you have bags, but this ride was three minutes. Much better than the $20 USD we got charged for the same route a couple of nights earlier.

We had an early morning coming up so opted for an early night. This was truly terrible timing, as it was Bob Marley’s birthday, and every bar along the beach was blasting music. 

Croydon In The Mountains

The next morning we started the third and final chapter of our trip – exploring inland Jamaica. We had our own driver for the day, Leroy. He charged us £130 for a full day of driving and waiting at our stops. The first leg was a very bumpy road up a mountain towards Croydon in the Mountains.

We booked a tour of the plantation from which the official Jamaican National Hero, Samuel Sharpe, was born and enslaved. He led a peaceful strike of the slaves within the plantation to protest slavery. He was jailed and later executed for this in Montego Bay.

Sculptures commemorating Samuel Sharpe uprising at Croydon in the Mountains

We didn’t know this at the time of booking. While fascinated by the history of the plantation itself, we had actually gone to what was described as a ‘coffee and pineapple tasting tour.’ Two obsessions of ours. Croydon Estate is a 132-acre farm home to 16 varieties of pineapples, coffee and honey production, plus many other local seasonal fruits.

Coffee and honey production facilities at Croydon In The Mountains
Pineapple plantings at Croydon In The Mountains

The tour was a little bit odd and slightly disorganised. We tried two different pineapple varieties, but thought we would be able to try all 19 that grew on the plantation. Coffee was in short supply and served with lunch at the end of a tour which started at 10am, when I was desperate for a coffee.

Banana plants and fruits

We learned as we were leaving that this was not even the first tour, but a test tour. The other guests were travel operators who would go on to sell the tour. We met the new owner of the plantation at the end. He was very hospitable, showing us a few special things and bringing us more fruit, but he did tell us that a few things were left off the tour. This was disappointing for us.

Plates of fresh seasonal fruit at Croydon in the Mountains

Once they get into the rhythm (surely by the time anyone is reading this), it will be a worthwhile tour. It was on the expensive side at $65 USD each including lunch and a taste of tons of fruit which grew on the plantation.

For an extra $35 USD they would include transfers to/from Montego Bay. They were also kind enough to provide lunch for our driver Leroy, who would have had zero other options at the top of this mountain.

Black River

The next stop was the very small coastal town of Black River. We stayed in the only hotel in town, Waterloo Guest House. The price was a bit silly, just $6000 JMD or £33 for the night. It was, as you can imagine, very basic but all we needed for a one-night stay.

Boats and shacks on Black River, Jamaica

We dropped our bags quickly as we had a destination we were both very excited for…

Floyd’s Pelican Bar

Floyd’s Pelican Bar is built on wooden stilts about 500m out from the coast on a shallow spot of the water where pelicans come to hang out. It was originally built by Floyd as a place to hang out with his fishing buddies, but it is now a well-established tourist destination in Jamaica.

Boat heading out towards a bar on stilts in the ocean in Jamaica

We had asked the hotel in advance how to find a boat to take us there, and they told us ‘just to go to the bridge.’ Black River was much more local than Negril and didn’t appear to cater to tourists at all. When we went to the end of the bridge, a guy named Rasta George appeared and told us he could take us for $6000 JMD round trip. This was the same cost as our hotel.

Floyd's Pelican Bar in Jamaica

We had been told by Floyd himself, who was very friendly and helpful in the lead-up to our visit, to expect to pay $20 USD each round trip. This was right on point and we didn’t haggle. What we didn’t expect was for a car to come pick us up to take us down to the boat. This made both of us very uncomfortable and we walked away to call Floyd and ask what he thought. Floyd said he knew Rasta George, so we reluctantly got in the car. It took us to a small boat on a dark sand beach about five minutes down the road. As we were getting on the boat, we saw two pigs frolicking on the beach.

It was a quick boat ride out to Pelican Bar, which was absolutely heaving. We got two Red Stripes at $500 JMD each. Unbelievably reasonable for a bar that needs drinks boated out. Our legs hung over the side of the bar as we drank them. We had our names engraved in the wood. There were crabs and pelicans, and it genuinely felt like the bar had been adopted by the sea.

We saw a large boat full of people start to leave, and realised that tourists must have treated this as a day trip from Treasure Beach rather than treat Black River as a stop of its own. There is a ‘bathroom’ on the bar, but it is actually just a semi-private area to pee onto a hard surface which dribbles into the water. I opted for this rather than underwater self-soiling, which I just cannot get on board with. BYO toilet paper.

Cases of beer stacked up on Floyds Pelican Bar in Jamaica

We ordered a lobster and a red snapper Escovitch (local style prepared with pickled veg) prepared on a grill. By the time our food arrived, the bar had really cleared out. There were 10 people and one large crab in the main bar.

Our ride promptly arrived at 6pm, as we had asked him to, and we went back to Black River the way we came. The driver dropped us right off at our hotel, too.

Crabs walking the planks of Floyds Pelican Bar in Jamaica

If we were to go again in the future, we would 1) go earlier in the day, as the bar loosely ‘closes’ at 6pm and it gets a bit windy, and 2) we would spend the extra $1500 JMD and go to J. Charles Swaby’s, an actual tour company that you can walk to, to get a boat all of the way to and from Pelican Bar rather than get in a car from someone we met in the street. We didn’t know this was an option until the next day.

Black River Local Spots

With an early dinner already in, we ‘hit the town.’ There wasn’t much to it. We went to Tasty Foods, where we got hit with our first blatant tourist tax for a couple of beers. “The menu on the wall is old, the price is actually an extra $100 JMD.”

Tasty Foods

Feeling resentful, we left to explore, and found the only bar in town, G’s Cool Spot. After a couple of beers while we chatted with locals, we went to bed as we had an ever bigger day of tours the next morning.

G’s Cool Spot

We woke up early to pack and get breakfast as our first tour started at 9am. Options were… limited. Not that we’re complaining that we had an excuse to eat at Juici Patties for breakfast. We each got a beef patty for a meagre $250 JMD a piece. It was due to open at 8am, but it was heaving by ten to.

Juici Patties

A Crocodile Safari down Black River

Coffees in hand, we headed down the road to J Charles Swaby’s, for a crocodile cruise through Black River.

The first tour was at 9am, which wound up being private, as no one else had turned up. It was $7500 JMD for the cruise for both of us (cash only) and it lasted just over an hour.

A seagull flying low over Black River in Jamaica
A crocodile in Black River, Jamaica

We learned that in the mornings the crocodiles like to sleep, and tend to come out in the afternoon. Halfway through the cruise our captain called out for Philip. Philip was a local sixteen-foot crocodile, but he didn’t come!

Mangroves on Black River, Jamaica
A boat on Black River, Jamaica
A heron flying low over Black River, Jamaica

We only saw one crocodile on our way out and the same one on our way back. Our captain showed us the crocodile nursery afterwards, too.

Baby crocodiles and fish at a crocodile nursery
A large crocodile sunbathing in Jamaica

YS Falls

We walked back to our hotel where Leroy was waiting to take us to YS Falls ($7500 JMD entry for two). These are a series of waterfalls about an hour north of Black River. We had almost skipped this as a destination as it sounded very touristic (think ziplines over waterfalls) but I’m so glad we didn’t. It was beautiful, and we walked across the waterfalls. If you were in Europe it would have been spoiled with fencing and walkways. Instead we got to walk over slippery rocks with the force of the water trying to push us over. 

YS Waterfalls in Jamaica

There was a beautiful newly renovated pool with muskoka chairs and a reasonably priced bar ($350 JMD for a beer!). We could have easily spent a couple of hours soaking up the sun in this beautiful oasis smack in a field surrounded by mountains. This was unexpected, and I wish we had budgeted more time to spend here. Unfortunately, we had a 1pm tour that we had to catch, so we quickly changed clothes and left. A small caddy bus took us back to the entrance through a field of cows. 

We had specifically left enough time to stop for a quick roadside jerk chicken and rice en route to our next stop. Leroy pulled over into a tiny town where we got two incredibly heavy takeaway boxes and a couple of Red Stripes from a wooden shed with an oil drum grill. This was the best rice we had on the whole Jamaica trip, and you could really taste the coconut.

Roadside Jerk hut in Jamaica

Appleton Estate Rum Distillery Tour

Paz the donkey crushing sugar cane at Appleton Estate

Whenever we visit a Caribbean island we always do some research into the rums of the island. Often there are distillery tours you can join which can give great information on the production methods and varieties of rums, but also insights into the history and culture of the islands.

Appleton Estate Rum Distillery warehouse with palm trees outside

The rums from the Appleton Estate are world-famous, and as soon as we booked our trip to Jamaica we knew we would be going on their rum tour, which takes place hourly five days per week.

Distillery equipment at Appleton Estate Rum Distillery
A sign saying 'Store Positively No Naked Lights' at Appleton Estate Rum Distillery

Our welcome rum punches were easily some of the best we have ever had.

Appleton Estate Rum Punch

We went on a tour through their gardens and distillery, followed by a tasting of their three entry-level rums.

Peacocks in the Appleton Estate gardens
The Barrel Room where Appleton rums are aged

We got a discounted rate of £22 each through booking on Viator and an additional 30% off through Quidco and Amex offers, but it’s usually $39 USD per person. Paying $39 is quite steep for what you get but £22 was reasonable.

A night out in Montego Bay

Leroy was waiting for us to take us to Montego Bay for the last night of our two-week trip to Jamaica. On our drive in, I needed to use the bathroom. We accidentally wound up having a pit stop in a strip club.

Sunset at Margaritaville

As we approached the city, he gave us a few pointers on our way in. Like how on Wednesday nights there was a party at Pier One, a large outdoor bar on the water. He dropped us off at Caribic House Hotel ($112 USD per night) right on the Hip Strip. We quickly dropped our bags and headed across the street to Margaritaville to watch the sunset. While we still hated what Margaritaville stood for – catering to tourists to just want a taste of home rather than experience Jamaica like a local – this one was right on the water and had an incredible view that no other bar on the Hip Strip had. There was a water slide that went from the second story of the bar into the water. We did not use it.

Pier One Party

So we had a couple of both overpriced and warm beers there, and then walked towards Pier One for the Wednesday party. On the way we passed Pork Pit. This was the most authentic jerk we had seen on all of our trip. Pork and chicken slow-cooked over enormous smouldering charcoal grills. We were both eager to eat here but kept walking, thinking we would go on our way back from Pier One. When we arrived, a good 25-minute walk from our hotel, we didn’t see what the fuss was. It was a very large bar and the food menu was predominantly American. We sat at the bar. There was a family behind us celebrating a child’s birthday with cake.

Pier One

By the end of our second drink, things were ramping up. Staff were moving tables around and running back and forth getting things set up. We asked the bartender what was going on. He said there was a fashion show and party at 10pm. Obviously, we needed to attend, but we had walked right past Pork Pit already, and now Pier One was charging cover for entry. Sam and I are old and don’t pay cover charge for bars. Fortunately, the hostess at the door found Sam’s British accent charming. She promised that if we left, we could come back without paying for entry. 

Pork Pit Pit Stop

We made a dash for Pork Pit. When we arrived it was before 9pm but they were already out of their famous pork. We opted for a portion of chicken and sausage and topped it off with the delicious in-house hot sauce, and told ourselves we would return the next day for the pork. The pricing was beyond reasonable. We spent around $2000 JMD / £10.50 on our food and two bottles of Red Stripe. What a place to have next to your hotel.

We rushed back to Pier One to get there for the “fashion show,” but our bar seats were long gone. All seats were long gone. It was officially full, and there was a stage on the outdoor deck lit up. We stood near a service area of the bar with a drinks menu in hand, only for the waiter to take it away. “The prices go up now. There’s a party.” Prices for everything went up about 50%, but no one knew how much anything cost when ordering. There was no revised menu.

We got into the Appleton Reserve 12’s, pineapple and lime juice, and bitters. All while we watched models parade the stage in clothes and then lingerie. Apparently one man sponsored the entire evening, and every 15 minutes the MC would wish him a happy birthday and tell the audience how essential he was to the party. After the fashion show, the dance floor broke out with the models at its centre. It was equal parts confusing and entertaining. I would highly recommend this party to anyone in Montego Bay on a Wednesday night.

Our final day in Montego Bay

We woke up on the slightly hungover-side, and packed up our bags for the third morning in a row to check out of our hotel. Our flight was that night at 21:30, with the airport just a few minutes drive from the hotel. It was a whole day to spend in Montego Bay.

Coffees on the terrace at Caribic House Hotel

Breakfast at the Pelican Grill

We started with brunch at The Pelican Grill, as any write-up on Montego Bay mentions eating here. We had briefly passed the night before but opted for Pork Pit instead for a quick bite. Sam got an absolute classic Jamaican breakfast of ackee and saltfish with sides of callaloo, plantain, yam and dumplings, and I got an omelette and bottomless coffees. It was good, but nothing mind-blowing enough to bring it to institution status. It was very nice to have bottomless coffee and ice water on this particular morning, though.

Traditional Jamaican breakfast at Pelican Grill

Downtown Mobay

Downtown Montego Bay was only a 15-20 minute walk away from Hip Strip. We wanted to see the main square and the Sam Sharpe monument as well as a couple of other sightseeing bits. Neither of us realised quite how touristic Hip Strip was until we got here. We couldn’t take a step without someone running up to us, trying to con us for money. “I recognise you from the airport, I handled your bag, how about a tip?”. Or just trying to talk to us about anything and everything. Generally, after acknowledging people, we would just keep walking, but after a week in Jamaica we had learned this is considered offensive. It was difficult.

Samuel Sharpe Memorial and The Cage in Downtown Montego Bay

When we got to Sam Sharpe Square, somebody who was not all there picked Sam out of the crowd and starting threatening and aggressively shouting at him, even banging loudly on a steel door. A local came up to us and kindly told us we should think about leaving the area. We were already a bit on edge and this made it too difficult for us to enjoy our time here. We got a patty at Tastee Patties (Juici Patties’ competitor in the chain of fast pattees) and headed back to Hip Strip. Between Tastee and Juici, we enjoyed them both. Juici had more liquidy filling. Tastee was, in our opinion, more tasty due to the spicing and less liquid state of filling. Both enterprises get points for accuracy of their business names.

Tastee Patties

Pork Pit Round 2

As if we hadn’t eaten enough at this point, we stopped back at Pork Pit for the pork they had run out of the night before.

The Pork Pit

We enjoyed it on their sprawling sunny patio. It was delicious and clearly their speciality.

Jerk chicken being smoked under corrugated iron in Jamaica

A Montego Bay Coastal Bar Crawl

We continued walking east down the Hip Strip in the hopes of finding some little bars along the beach. The beach bars were private and only accessible if you had paid for access to Doctor’s Cave Beach. It did look beautiful, and would certainly make for a great day, but we had just spent a week in Negril and we didn’t want to beach on our last day in Jamaica.

Tracks & Records

We stopped at Usain Bolt’s bar, Tracks and Records, for a very odd drink in a very quiet patio. Modest man.

Statue of Usain Bolt iconic celebration outside Tracks & Records
Tracks & Records

As we walked further from the commercialised area of the Hip Strip, the beach became very small and uninhabited. A bit further along we ran into a few all-inclusive resorts who wouldn’t let us in.

Wingz & Tings

At the very end of the road, literally right next to the airport, we got a beer at Wingz & Tingz, which overlooked the beach. It really felt like we had done the centre of Montego Bay. We hopped in a taxi to go to what was heralded as one of the best places in all of Jamaica to get jerk – Scotchies.

Smokeez Bar

Smokeez

On our way out, we saw a string of bars along the water. As we could not have physically eaten at this moment anyway, we asked the taxi to stop about a 10-minute walk away from Scotchies. Without our hopes too high, we walked into a bar called Smokeez. We were delighted that it was an amazing bar. It had picnic tables in the sun, a floating bar next to a branded boat, a cat, and an incredible playlist. I could have spent all afternoon here, but greener pastures, etc.

We walked further away from Scotchies and there was a little village of bars side by side. They were all unnamed but apparently sponsored by Campari.

We opted for the bar with seats in the sun overlooking the road. It was owned by a guy who introduced himself as T-Bone. The girl sitting next to us ate four entire lobsters in the time that we drank two beers.

A pair of bottles of Red Stripe on a wooden counter in Jamaica

Apparently she bought them from the man who actually caught them, then paid a small fee to have them grilled here. We asked if we could get one, but the turnaround time was too long to actually get then grill the lobster.

Lobster and fish on the grill

Instead we continued to Scotchies for our final meal of our two weeks in Jamaica. 

Scotchies

We walked in to see the wide and shallow coal grills slow-cooking a sea of chickens.

Scotchies

Sitting at the bar, we ordered too many things and covered them in the in-house hot sauce. The chicken was incredible, and the stand-out item on their menu.

Grilled corn and meats at Scotchies in Jamaica

If you spend one day in Montego Bay, get pork at Pork Pit and chicken at Scotchies, with drinks at Smokeez in between.

The end of two weeks in Jamaica

With our cholesterol levels several points higher than at the beginning of the day, we hopped in a route taxi back to our hotel and headed to the airport in another route taxi. Even the airport was fun, with a bobsled in the middle of the halls.

In two weeks we only scratched the surface of Jamaica. We loved the laid-back and (generally) friendly attitude of its people. We loved Jamaica so much that we have already decided we’re going to go back, but flying in and out of Kingston and visiting the north beaches and Port Antonio. Whilst it wasn’t cheap, it was significantly more reasonable than both Antigua and Barbados, and deserving of a return to see the rest of the island.


Advert for a jerk festival in Jamaica
Whiteboard menu in a Jamaican restaurant
Eating roadside jerk with Red Stripes in Jamaica

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1 comment

Susan Osmar March 9, 2025 - 5:21 pm

Fantastic article. You definitely captured the soul and spirit of Jamaica. I respectfully suggest that you go to Doctors Cave on your next visit. It’s as good, if not better than 7 Mile Beach. Happy travels.

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