Have you ever felt like the universe was on your side? Or, conversely, it conspired against you? This is a travel story of both sides.
For the former, stars aligned to open a path for me to Thailand. In January 2025, I learned that a group of gay Australians I had travelled with before were going to Thailand for two weeks in February. They invited me at the last minute, on a lark. Oh, what Thailand taught a gay traveller.
I balked initially. The flights would be too marked up. Yet, as the dates drew near, I started experiencing the Baader-Meinhof phenomenon, more commonly known as frequency illusion. That’s when you learn something new and suddenly you see or hear it everywhere. My word was “Thailand,” and it called to me. The protagonist of a book I was reading recalled his days in Bangkok. Without consultation, friends booked dinners at Toronto-based Thai eateries. The third season of one of my favourite shows, The White Lotus, was set in Thailand. To top it all off, I had a three-week break in work contracts and would sacrifice neither vacation days nor job opportunities by going.
So after hemming and hawing, I bought a flight to Thailand just three days before departure, aided by the fact that this rag-tag group of queer Aussies had reserved mostly Airbnb and other rental homes, making it easier for me to slip into their plans than having to adjust hotel reservations. Off I flew, a gruelling 23-hour journey with thankfully only one layover. Oh, what Thailand taught a gay traveller.
The spur-of-the-moment choice was very aligned with the type of traveller I am. I’ve found that when it comes to making decisions on a trip, there are two types of people. The first—and very much my tribe—are those who see romance and excitement in the unknown and leap at opportunities. Let’s call them “jumpers.” The other type of traveller is more cautious, viewing their experience of a trip as a matter of wisely allocating limited time and funds. We’ll call them “planners.”
In this group of eight gays, the jumpers had a large majority. After all, these are the people who invited me on a trip weeks before leaving—and I was taking them up on it. All told I’d say we had one strong planner; another was a “planner rising.”
Our planner had mapped out a route that would have us experience all facets of Thailand. We’d start in the bustling national capital of Bangkok, head north to the lush jungles and reverent temples of Chiang Mai, return south to beachy tourist mecca Phuket, and finish the trip off visiting the serene islands of Koh Tao and Koh Samui.
Arriving in Bangkok, a city of 17.4 million, I got the sense this would be a journey characterized by motion. The downtown core is in constant flux—a push and pull with its cyberpunk-urbanist aesthetic. The city’s massive Skytrain metro track arches above countless motorbikes, tuk-tuks (three-wheeled cycle cabs) and people zooming around.
Much business is done not at counters and kiosks but on the streets themselves. Vendors set up booths to sell meats, seafood, fruits and tchotchkes. People line the sidewalk, beckoning you in for massages, a meal or to see their wares. Catnip to jumpers, who are easily convinced and distracted.
This phenomenon continues into the city’s gay district. Silom Soi 2 and Soi 4 seem at first like unassuming side streets, but at night they are packed with people occupying the bars and dancefloors. Walking under the lights of Silom Soi 2 and Soi 4 you’re pulled in and caressed by representatives of the venues. Some are waiters trying to entice you with a drinks menu. Others are performers, shirtless male dancers, beautifully adorned drag queens and trans women.
Here’s where being a group of jumpers in a place like Thailand can be a drawback. The way these bars do good business, I quickly learned, is that in addition to/instead of a cover fee, they ask you to pay for three or four drinks at the door before entering. It’s a smart play. What’s framed as a good deal (saving money by pre-purchasing drinks) is a way to keep you inside, even if the bar is more barren or grungy than you imagined, or the show isn’t very good. You either leave for greener pastures, forgoing your already paid-for drinks, or you suck it up and stay a few rounds, giving other patrons the illusion this is a bar or club you want to be in. In other words, you jump and then you’re stuck.
These strategies extend beyond the nightlife. On an attempted visit to Thailand’s Royal Palace—a gold-topped estate, home to the royal family—we were turned away due to a private event. Right at the marble gates, a man who seemed like a passerby asked if we wanted any suggestions for what to do instead. He hailed a cab for us and gave the driver directions to a nearby Buddhist temple.
Hoping to salvage the day, we naively hopped in. Instead of a temple, we pulled up to a clothing store—the driver told us we should go take a look. We politely complied, assuming perhaps this store specialized in local fabrics or had some cultural significance. Nope: it was a typical (high-priced) clothing store, with vendors eager to measure us for custom looks. When we quickly left, the driver encouraged us to take another look.
It was an odd feeling, wedged between my very Canadian desire to be nice and go along with him and the fact that we had already paid the driver. Fortunately, the planner of our group was less delicate. He insisted that the driver take us to the promised temple. After two more attempted stops—at a food stand, and a boat cruise—we made it. By then it was clear: the man outside the palace and the driver had coordinated taking us to pre-ordained stops. It was a rinse-and-repeat tourist cycle, one that ate up a chunk of our day, and more than a few of our bhats.
I don’t blame Thailand’s vigorous hustle culture on its people. They’re spurred by a tourist economy hurt by COVID as well as tsunamis and earthquakes. In March, Thailand and its neighbour Myanmar were hit by a 7.7 magnitude earthquake. Tourist dollars, enthusiastically given or not, are a crucial ingredient to recovery. Similar tactics play out at all major tourist destinations.
The problem: as a group of jumpers, we were putty in their hands.
We decided to resist. Barely halfway through our trip, we were determined to shake our nativity and become planners.
Rather than revisit the gay district the following night, we went to the House of Heals (Renaissance Bangkok Ratchaprasong Hotel, 518/8 Phloen Chit Rd., Bangkok). It was a venue farther away from the queer core, but one I knew through Pangina Heals. The host of Drag Race Thailand and contestant on RuPaul’s Drag Race: UK vs. the World ran the night. Though House of Heals also has the required drink spend at the door, this time we were more than eager to stay.
We were offered luxurious couches to sit on and watch a multi-act drag show featuring some of the cast of Drag Race Thailand. It was an exceptional show with a level of glamour, showmanship and choreography that got us off our seats more than once. That’s not to say it was cheap or a hidden gem, but it was a quality indulgence. I even bought a House of Heals branded T-shirt, perhaps the most quintessential “gay tourist” purchase ever.
Reinvigorated, we tried to keep that spirit of planning alive throughout the rest of the trip. In Chiang Mai, when flyers were shoved in our faces with activities, we googled names of businesses and read reviews. That day-of research proved fruitful, and although the city, which has a population of about 1.2 million, is better known for its connections to religion and spirituality, we found a queer gem, 6IXCRET (Night Bazaar Tha Phae Rd., Chang Khlan, Chiang Mai), which had impressive drag and dance shows on par with the much larger and more popular House of Heals, featuring fire tricks and elaborate costume changes.
We applied our new discipline beyond queer bars, too. For example, we were approached on the street in Chiang Mai by a “local wildlife guide” who offered us access to all kinds of Thai animals. Instead of jumping at the chance, we read the business name on his red vest and googled it. After seeing online photos of caged, fearful and patchy foxes and monkeys, among other creatures, we were immediately grateful we hadn’t given him our funds.
Instead, we found an elephant sanctuary that required all guests to sit through a presentation pointing out differences between ethical and exploitative care of elephants. It was worth the bit of homework, as we still got up-close and personal with the majestic animals. It’s the quick “ride and a photo” places that treat the elephants the worst, our guide said. The type of place that sends guides to approach you at the train station, just as we were approached.
Though more savvy, we hadn’t completely shaken our jumper roots.
Ironically, the next time our group of eight gay men were swindled was by cis women at a strip show. This took place in Phuket, a resort city of about 80,000 people—the capital of the province of the same name. Tattoo studios, weed shops and bars line its sprawling beach. With its reputation as a place to party, Phuket was begging to compromise us. We were so eager to see one of the “ping-pong shows” that have made Thailand famous as a sexually wild destination that we skipped the careful research and consideration we had devoted ourselves to for the last few days.
Walking Bangla Road, the epicentre of sex shows and partying, we were approached and offered “the best ping-pong show in Phuket.” We had spent the day drinking in the sun. Our jumper tendencies kicked in and we let ourselves be swept inside, agreeing to pay the comparatively enormous 1,000 Baht (approximately CA$42) entrance fee each.
The price suggested a certain pedigree—and we weren’t let down. The show was impressive, watching not only ping pongs but bananas, beer bottles and a live bird fly out of a woman’s privates. Yes, a live bird.
But it’s what happened between the shows that was the tourist trap. When we ordered drinks, they arrived in the hands of beautiful, topless Thai women. They encouraged us to drink them from their breasts, and we obliged. They sat with—or rather on—us the rest of the night.
It was a magical evening—until the bill arrived. Instead of just charging us for drinks, which we had expected, this group of gay men had apparently bought a series of lap dances and time with the ladies, despite never asking for them, or being told their “presence” would be an expense. The few rounds of drinks was nearly CA$500.
Why would a group of gay men accept these women’s advances in the first place, no questions asked? It’s a fair question, the answer for which I can only attribute to a lack of sobriety and the “try anything” spirit that jumpers hold as sacred. You have to say yes, because when else are you going to get this experience?
Turns out, not everything should be experienced. Our sole planner stood up—righteously and tipsily—to say we would not be paying the bill. I cringed, but I also admired him. His position quickly changed, though, when security was called. The bill suddenly seemed like a small matter compared to a night in Thai jail.
The incident dented our wallets and egos. But we licked our wounds on the breathtaking islands of Koh Tao and Koh Samui. They were the perfect places to recoup: mountain paradises lined with winding roads and stunning resorts.
The image perhaps most ingrained in my mind is a sunset on Koh Tao, which we watched from an infinity pool that seemed one with the peaceful ocean. It was an experience that needed no peddling, no negotiation, no spontaneity, no planning. It was just natural beauty, something Thailand truly delivers. It was a priceless view that planners and jumpers alike could enjoy.
