The two most fun days of my life took place in Trinidad for carnival 2019 (see Last Minute Trinidad Carnival Guide! Everything You Need to Know And Stuff You Will Figure Out On Your Own!). Following that blissful event, I decided to incorporate a yearly carnival as part of my travel plans. Covid had other ideas and delayed that adventure year after year (see Jamaica Carnival Postponed till July). I finally was able to go. Here is what I learned: What Not to Do In 2023, with life mostly normal, I booked the Courtyard in Kingston on points. For 100k points, I was able to stay for five nights. While this is a good deal in terms of points redemption, it was a mistake for two reasons:

1. I should have stayed at the new AC Marriott. It is a gorgeous property with a Starbucks in the lobby. More importantly, it costs the same amount in points. The reason I booked the Courtyard is that multiple websites recommended it for a Carnival stay. More on websites and recommendations below.
2. Great deal notwithstanding, 5 nights in one place is a violation of TPOL’s well-established Travel Philosophy where stays are capped at 4 nights maximum. For carnivals, the stay should be as short as possible. In Trinidad, I booked last second, arriving the night before the march began. I should have done the same here (see Travel Lesson: Too Much Carnival). The events leading up to the march were money grabs. Though they incrementally improved, they were amateur and uninspiring.

If you’re going to the full moon party in Thailand, my advice is to skip the actual full moon and enjoy the nights building up to the main event . During those nights, you’ll meet people from all over the world and create a nice organic community that Leo would endorse (see Full Moon Party Thailand: 3 Times Wasn’t Enough. Maybe Once More?). I thought I could replicate that model in Kingston. I did not because 1. Kingston is a city, not a quaint beach town. 2. There were too many simultaneous events, making it impossible to form a close-knit group. Costume Pick-Up Illuminate On Wednesday, I paid $65 to go to an event called Illuminate. It was a large concrete parking lot with a DJ. Although there was an open bar and good soca music, there was no energy. I opted to pay for jerk chicken and go home.

Sleep In Trinidad, I barely slept. I don’t know how I had the energy to go as hard as I did. In Kingston, I was the most rested reveler on the island. With nothing planned for Thursday, I slept the day away.

Jangas I paid $30 to go to another fete, carnival for party, at a bar called Jangas. Again, the music was good but I could not figure out how this was carnival. It was no different than going to a nightclub in any city. Tailgate I met a few partyers at Jangas who had purchased tickets to an event called Tailgate. For the magical price of $65, entrants could go to another concrete lot and listen to soca music. I arrived at the venue was asked to pay and decided to go home. Once again I spotted chicken to go. Unfortunately, it was cash only, leaving me frustrated and hungry. Sun Nation I will give credit to the carnival organizers. They know how to set up an Instagram and promote the events. Uninspired by parking lot parties and nightclubs and a desire to get out of the city, I paid $230 to go to Sun Nation. The event consisted of a booze cruise, a stop at an island for more partying, followed by a sunset return. The problem with booze cruises is 1. I’m too old for this shit. 2. It reminds me that I am too poor to afford a yacht (see Porto Cervo, Sardinia: My Yacht Is Bigger). 3. There’s a risk that it could be boring, leaving me stuck on board.

I was proven correct regarding 1. And 2. This was confirmed when we reached the sandbar (not an island), and I saw people in private boats, cruising at their own leisure. As for 3, I had enough rum to make the most of my time.

TPOL’s Tip: Arrange a ride home in advance. Post booze cruise, I found myself at Port Royal, about an hour from the Courtyard, with no ride home. Luckily, the photographer drove me home for free. To Juve Or Not? That Is the Question When I went to Carnival in Trinidad, I participated in J’ouvert, a party that starts in the wee hours of the night and ends with clothing covered in paint early in the morning. As the old grouch that I am, I was happy when I found out that there was a breakfast party on Saturday that began at 8AM. That was the excuse I used to justify skipping the juve affair. TPOL’s Tip: if you are going to do J’ouvert, I was told to do #ambush, a private J’ouvert at an undisclosed location. Last minute, I almost went but could not buy tickets online and the ticket seller was only accepting cash. Despite riding around for an hour trying to link up with the organizer, I could not locate her. That saved me $160 and left me well-rested for the next event. Breakfast Party Nothing I had done thus far had the vibe of carnival. I was told the breakfast party was worth the $230 admission price. Once again, I was in an Uber headed to a venue far from Kingston. This time, instead of concrete, there was a grass pitch. This time, instead of bailing out early, I drank the day away. You’re never too old to day drink, but again, how is this carnival? Concert? Carnival in Jamaica culminates with the march that begins at 10am on Sunday. Saturday night, there was a concert. Disappointed enough and overspending money, I skipped it in favor of sleep. Maybe It’s Me You may be saying that I am a miserable person who does not know how to have fun. Some revelers I met would agree with you. I disagree. In Trinidad, I was too happy for my own good. That high is how I ended up crashing my face into the pavement in Grenada two days after leaving Trinidad (see Surrendering Vacation: When to Cut a Trip Short ). In Jamaica, it was the exact opposite. The good vibes and sense of community were replaced by cover charges and selfish Instagram selfiers. This was a manufactured event that Holden Caulfield would not want to be a part of. Proven Correct? I received this email from my band. Women spent hundreds on costumes and many did not receive what they were promised. The costumes looked like a school project from a school child who fell in love with scotch tape and Elmers glue. I spent $350 and received the wrong size board shorts and a tee shirt that I opted to remove halfway through the day. Judgement Day: The  March The trucks were on the road. The music was blaring. The alcohol was flowing. But where were the people? Could it be that even the marquee event was a flop? From 10AM till lunch at 1:30PM, this appeared to be the case. Like all the other events, there was no energy. There were moments of hype, but many more moments of meh. At lunch, I contemplated bowing out and going home.

Starbucks This is probably cheating but I stopped at the aforementioned AC Hotel for a double espresso. I can confirm that the hotel is much nicer than the Courtyard. Thank You Alcohol Perhaps it was Appleton Rum #14 or Johnnie Walker #7 but at some point something clicked. The music was right. The crowd was right. The vibe was there. I had found my carnival. After Party? In Trinidad, the march ended at the venue of the after-party. Here, the march ended at a Popeye’s, leaving everyone wondering what to do next. I was about to walk home with a group of people, as I do not suggest solo walking at night in Kingston, when I saw another band still marching. I jumped in their group and danced for a little longer until their march ended. After Party? I was denied entry to the other band’s after-party. Somehow, I made it back to the Courtyard and found the location of my after-party. It was in a huge venue. Getting in was scary. People were being squeezed and in danger of being trampled. Once in, it was another big DJ event in a concrete lot. Once again, I opted for chicken instead of alcohol. I Drove All Night Celine Dion once sang that she would drive all night to get to me. As someone who has driven cross country leaving at night to arrive in the morning (once from Michigan post-GM firing (buy my book, Everyone’s Advice Is Wrong . . . Including Mine) and once from Montana to Scottsdale (see TPOL Moves to Scottsdale: My Drive to the Desert), I will apply ‘get out, get in’ mantra to future party benders. Let me explain: I should have arrived in Kingston on Friday, picked up my $350 board shorts and juve tickets then went right to sleep. Saturday, I should have gone to Juve, then the breakfast party, and gone right back to sleep. Sunday, I should have gone to the march when I was good and ready. Sunday night, once the sun went down, I should have also gone down. Overall My mistake was arriving in Kingston too early. This mistake persisted as I also arrived at all other events too early. By the time it was showtime, I could not be bothered to be engaged. Fortunately, I did not give up on the day it mattered most. Those few hours gave me hope that I might not be that miserable.