It’s taken me a year to make this post. This is from a solo trip back in November 2015.

Montego Bay, Jamaica, November 2015.

I’m back from a five night, six (6) day solo trip to the northern coast of Jamaica, around Montego Bay. It was my first time visiting the country. Like any other first timer, I found it was filled with preconceptions.

Jamaica has a sketchy reputation amongst travelers, for whatever reason, yet its still one of the most visited tourist spots in the region. It sits right below Cuba, which you get to see from the airplane window on the way there.

All my plans were put together at the last minute in about a month. I had no prior plans to go. I lucked into getting a free flight on Southwest Airlines using frequent flier miles. It was a trip of serendipity to celebrate my 44th birthday on November 11th.

A few weeks before I left, a Jamaican food festival/charity event called Nyam Jam was announced at Goldeneye, the exclusive resort owned by Chris Blackwell. It was hosted by chef Mario Batali and Chris Blackwell, whom I wanted to meet, as he’s such an iconic figure in the music having started Island Records (U2, Bob Marley). Of course, the odds of this event happening on the same week I was going to be Jamaica was one in a million. Serendipity. It happened.

I quickly bought a ticket to that event as it was occurring on my last evening there, such an amazing coincidence.

Being on a solo trek, I had no one else to worry about. I’m an avid reader, usually read up on tour books and other online websites. As usual, nothing can prepare you for actually being there, the pace of the place sets the agenda more than anything else.

Before arriving, I read accounts how “crazy” driving in Jamaica is – people say it’s dangerous to drive, roads are awful, etc. Blah, blah.

More nonsense people who are terrified of travel itself, I later discovered.

I did not want to hire a taxi and be shuttled everywhere – it’s costly, time consuming and limits spontaneity.

I took the risk and rented a car from Thrifty Car at the airport. It was only $250 for a week. I had car insurance on my AAdvantage World Citi card.

I found driving in Jamaica to be relatively easy. No problem, mon! I kind of enjoyed the thrill of driving on the wrong (opposite) side of the road the British way. The main highway road, at least in northern part of Jamaica between Montego Bay and Port Maria, was well paved and easy going. There were some potholes and road construction, but you get that anywhere, including here in USA.

I didn’t have any problems driving and most of the negativity was unfounded, in my opinion. Jamaicans do drive a little crazy, but it’s not a big deal. I’m an experienced driver and don’t get stressed out in new environments. For most people, however, I can understand it might be intimidating to drive here being on the wrong side of the road. So, for that reason only, I don’t recommend it except for the savvy driver.

Also, the roads and infrastructure once you get off the main highway were not in good shape. I wish I had a 4×4 utility vehicle, my little economy car struggled in some of off main road areas. However, overall, driving was a positive experience and I’m glad I did it.

I first arrived in Montego Bay, which I found to be chaotic and congested. I didn’t like it too much – kind of a dirty, not very picturesque in the main center of town. However, the bed-and-breakfast I stayed at, Polkerris B&B, was amazing with a nice view of Montego Bay. An island of paradise in an otherwise not too interesting part area of Jamaica.

On my first night there, I met a mother and son visiting from England, Sandra and Ollie. Ollie was a cool kid, really into photography. I struck up a conversation with them and I told them I was going to try and visit some locations of the first James Bond film, Dr. No.

Sandra mentioned she still plays bridge with Una Trueblood in London, who was Ian Fleming’s secretary and the inspiration behind Ms. Money Penny. 

Like what are the odds? I believed it.

Sandra, modestly, said Una wasn’t “too good” of a bridge player.

Chris, the manager of Polkerris, was a great guy, too. I highly recommend Polkerris B&B to anyone wanting an unique place to stay in Montego Bay outside of the mega resorts. A first class experience.

I had one great meal in Montego Bay – at the famed Scotchy’s Jerk Chicken. It lived up to the hype.

Chicken grilled on local woods under metal cover, basted in jerk seasoning, it’s friggin’ delicious. It was so good, I ate there twice.

At Polkerris, I tried the Jamaican dish of ackee and salt fish, which is a staple here like eggs and bacon. Ackee is a kind of bread type fruit which resembles eggs, and has a high fat content. The fish was also pretty oily and salty tasting. Together, it’s a massive gut bomb. Gross, man. It blew up my digestion.

I couldn’t eat more than half without getting full. I got a bad case of the runs afterwards. It wasn’t a good experience, unfortunately.

Maybe if I had the digestive enzymes for it (like locals) it would have been ok. But that’s the drawback of eating “unusual” local cuisines in other countries.

I took off the next day and headed to the Riu Hotel Resort in Ocho Rios, which was one of those mega resorts all-inclusives that some people love or hate. I got it cheap at $140 a night. It was good choice.

One the way there, I made a pit stop at the White Rose Hall for a tour of famed house of the White Witch, who killed some of her slaves back in 1800s. Creepy good fun.

On the drive down, I passed the port where Christopher Columbus arrived. And I drove past this famous red manufacturing dome where they mine boxite, one of the precious resources of Jamaica. It was used as the location lair in the first James Bond film, Dr. No (1962), which I consider one of the best Bond movies.

Riu Ocho Rios has an amazing beach, truly spectacular. It was exactly what I imagined Jamaica to be like. I didn’t get hassled from locals on the beach either.

It has small coral reef less than 50 yards from shore, one can swim and see some nice fish less than 10 ft down.

The hotel grounds were nice, pools were great, staff pleasant, and all you can drinks flowed endlessly. I met some great people, lots of Brits were everywhere.

The major downside is the food in the upscale restaurants at night was bland. I didn’t enjoy a single dinner.

The buffet food and jerk chicken on beach was tasty enough, though.

After a couple days exploring around in the area in area around Ocho Rios (which didn’t have much to see) I took off to Port Maria and stayed one night at Blue Harbor, which is Noel Cowards’ old guest house where Hollywood royalty used to stay back in 1940s. It hasn’t been updated since and was in total contrast to the Rui mega resort.

It was bare bones, no frills, like going back in time to another era. No wi-fi, no AC, no modern amenities. Nothing. I totally loved it. I was the only guest on the entire property. I felt like I was being transported back into time, to another era.

That’s the beauty of travel, when you go to off the grid places such as Blue Harbor, which offer very little in terms of fancy amenities, you realize just how little you need anyway.

I stayed in an old room where Katherine Hepburn and Marlene Dietrich stayed, apparently. It had an absolutely beautiful view of the ocean, stunning.

The pictures of Dietrich and Hepburn aren’t just reprinted pictures in frames – they’re the originals signed in ink by both stars with salutations to Blue Harbor and Noel Coward. Just sitting there, on the shelf, decaying with sands of time. Ok!

I had the salt water pool all to myself, too, which overlooked the ocean. It was such a great find.

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For $75 a night I considered it worth every penny just for the views and seclusion alone. I loved it and would love to return one day.  Blue Harbor was a highlight of my trip, for sure.

On my last day, I visited Firefly, Noel Coward’s museum estate at the top of a hill overlooking the ocean, where he spent the last days of his life. Very beautiful and stunning vistas. I didn’t know much about him, but he was like the Andrew Lloyd Webber of his time.

I was the only visitor. The seclusion and views were amazing.

That evening, I went to the Goldeneye resort for the Nyam Jam Festival charity dinner. I got a free tour of the hotel grounds by the staff, very nice people. I felt like James Bond walking around on the property. It had that kind of vibe. Heck, it’s where Ian Fleming created James Bond!!

The dinner that evening was incredible. I got to meet some staff who work for the Chris Blackwell empire, all very nice people.  It was like an island dream that evening.

The food was outrageous and incredibly good. They served desserts of chocolate rum in tiny chocolate containers, delicious stuff. I had several until I couldn’t remember anymore.

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I got to meet Chris Blackwell, too, and managed to get my picture with him. Chris told me to “always think long term” in business and he “only worked with people (artists) that have something to say.”

Ernest Ranglin, the guitarist behind albums with Bob Marley and Jimmy Cliff, played music that evening. Ranglin was one of the first musicians Blackwell worked with in the 1960s. Long term, man. He also did some musical work on the first James Bond movie soundtrack for, Dr. No. Mind = blown.

I got to spend some time in Ian Fleming’s private villa, which is now available for rent at Goldeneye for the uber rich.

I loved seeing the colorful road side stands and restaurants in Jamaica. The people were nice, albeit some were aggressive at times in invading your space, but that’s the Jamaican way, mon.

There are truly some beautiful natural areas of Jamaica untouched by development.  But the poverty is widespread and there isn’t much to see outside of the resorts in terms of modern developments.

There appears to be the ruling class top 1% and everyone else is at the bottom, which is where our country is headed.

Below is a picture of one of the unfinished buildings (or houses) one sees driving down the main road – there are dozens of these unfinished and decaying structures seemingly every square mile. It looks like a war zone in certain parts. These buildings are everywhere. 

I was told they are added to over time (years, decades) when the owners find more money. It’s a hard concept to understand. They don’t look like they’re ever going to be completed.

Jamaica has its certain appeal. Did it live up to my expectations? In some ways, yes, and other ways no.

Had I had just stayed inside just Montego Bay, or the Rui Resort, I wouldn’t have had the same experiences. It takes courage and willingness to fail to go outside your comfort zone. That’s pretty much how I’ve lived my whole life. I got to experience both sides of the fence and enjoyed all of it.

Overall, I’m glad I went, and can check that one off the bucket list.