Back in the early days of this blog, I occasionally posted articles dedicated to failure. Those trips when – despite my best efforts – I had come home with only nettle stings and blurry exterior photos from some supposedly-interesting building or another.

Perhaps it’s a measure of how far I’ve come since then, that when I fail these days… I fail big. We’re talking failing-at-an-entire-country big. Total non-adventures.

In this post I’ll be covering three different countries, where I completely and utterly failed to achieve anything of note: the Dominican Republic, Singapore and the Bahamas. They might seem exotic, but here’s why these three places rank as my all-time least favourite travel destinations.

 

The Dominican Republic

I flew into the Dominican Republic last year, off the back of two very productive weeks in Cuba. During that time I’d experienced the joys of hitting rock bottom in Havana; I had infiltrated an unfinished nuclear power station as well as touring the country, visiting sites linked to the rise and fall stubborn endurance of the revolutionary Communist Party of Cuba. After all that I was on a high, ready for anything the Dominican might possibly throw at me.

Not that the DR had been my ultimate destination; I was heading for Haiti in fact, looking for vodou temples, and the Dominican Republic simply happened to be on my way.

I touched down in Santo Domingo, and before I’d even left the airport I had already sniffed out a wifi signal. After my forced abstinence in Cuba, it felt good to binge on bandwidth and I ate it up like an addict in relapse. The Dominican capital would be my base for the next four days, before I hopped on a bus heading over the border to the other end of Hispaniola. I had four days in a new country – it felt like a world of possibility.

Outside the airport I grabbed a taxi and that’s when I met Juan, my driver friend. I told him the address for my hostel: a cheap and cheerful place in the ‘Ciudad Colonial’ – aka ‘Old Town,’ aka ‘Red Light District’ – of the Dominican capital.

From the car windows, this part of Santo Domingo didn’t look overly appealing. There were some attractive buildings, granted, but they were almost lost beneath a grimy veneer. Rubbish overflowed from bins on streets corners, billboards weighed heavy with advertising for everything you might possibly want to buy; the alleys and doorways populated with a cast of the homeless, the lost and the desperate people who had slipped between the cracks of capitalism. Perhaps I hadn’t picked the nicest part of the city, but suddenly I found myself missing Cuba; although give it 10 years, I thought to myself, and Havana is probably going to end up looking more like this.

Along the way Juan was giving me some basic lessons in Spanish, bulking up the collection of phrases and greetings I’d picked up back in Cuba. Then, pulling up outside the hostel, he turned to me and asked for a significantly higher price than the guidebooks had suggested for such a journey.

Still, I paid him and I took his business card. It turned out this was just Juan’s thing: you could call him any time of night or day and he’d come out immediately. He’d be with you in minutes, offer local advice along the way, throw in some Spanish lessons, then get you swiftly to where you needed to go and rip you off with a smile. He may have been a crook, but during those four days he was at least my crook.

Before I could check into the hostel, I had to ring a bell to have the staff come and unlock the heavy, barred grill that was bolted over the entrance; a reassuring start. They gave me a quick tour, then warned me not to venture out onto the streets alone after dark. Instead, anything I wanted could be delivered by a courier on motorbike, for a nominal fee.

Just because I hadn’t initially planned on visiting the Dominican, that didn’t mean that there weren’t things I wanted to see. It should have been an interesting place – the nation was founded back in 1844, a tale of war, rebellion and shady secret societies. Santo Domingo was the final home of Bartholomew Columbus – younger brother of Christopher Columbus. The city’s famous sights include the Alcázar de Colón, a museum and UNESCO World Heritage Site inside the continent’s oldest regal residence, which was built here in 1510 by Diego Colón, the son of Christopher Columbus.

Not being a massive fan of art museums however, I passed on the Alcazar… in favour of the semi-ruined battlements that spread around the back of the building, and down along the riverfront on Avenida Francisco Alberto Caamaño Deñó. There were entrances, open doorways here and there, leading to the inside of the structure – but when I poked my head inside one I was received by an angry groan and the sounds of movement in the dark. Apparently, the place was already occupied.

Santo Domingo is home to the oldest cathedral in the Americas – the early 16th century Cathedral of St Mary of the Incarnation – though as I approached through Columbus Park I found the place somewhat underwhelming. The plaza was filled with tourists, and with beggars who prowled from bench to bench aggressively shaking their cups at foreigners.

In retrospect, I probably should have gone inside; but I’ve always preferred immersing myself in the streets of a new country rather than ticking off lists of UNESCO sites. I was desperate to find the heart of Santo Domingo on my own terms, not according to the recommendations of the local tourism board. I did try to investigate a smaller, quirkier museum nearby though – the Museum of Rum and Sugar Cane – but it was closed, even now at peak tourism season.

Not a long way from there, I went looking for an abandoned hospital that I’d read about; the ruined Hospital of St Nicolas of Bari. It had sounded interesting, but when I got there I found there really wasn’t much to see – just a few broken arches in the outline of a hall. When they’d called it ‘ruined,’ they meant it in the strongest sense of the word.

I was beginning to find that Santo Domingo exists as a juxtaposition of extremes. There are five-star hotels dotted about the city along with a swathe of UNESCO heritage sites and fine restaurants – a network of well managed tourist hotspots. But these places exist above and around an underbelly of vice and crime and violence. The city has a reputation for robbery and kidnappings as well as serving as a popular trans-shipment point for Colombian drugs on their way to Europe. In 2012 the Dominican Republic reported a murder rate of 2.2 people in every 10,000, ranking it the 20th most dangerous country in the world.

The role of the tourism industry here then is to create a protective bubble around its visitors; with the vast majority of tourists to the DR ending up at the all-inclusive resorts dotted along the coast. For someone like me though, this official tourism infrastructure felt far too prescriptive. Meanwhile, the other extreme would begin to seem increasingly – and aggressively – real. There did not seem to be much middle ground.

And so I retreated to my hostel, where stereotypical travellers sat behind metal bars trading stories and drinking beer that came delivered by motorbike courier… or splashing themselves in a small rooftop pool. I got to researching the city in depth, and that’s when I came across references to ‘la Alcantarilla de Ovando’; a network of tunnels beneath Santo Domingo reckoned to be the oldest sewerage system in the New World.

Worth a look, I thought. I grabbed my camera, tripod and torch, then headed back into town in search of the Dominican underground.

According to the website, the tunnels could be accessed through an opening in a park in the Colonial Zone… but I spotted the uniformed police surrounding the park before I was even halfway down the final block of Avenida Independencia. As I slowed my pace, assessing the apparent roadblock up ahead, someone hissed at me from a nearby doorway.

“Hey, USA!” he said. I ignored him, but he persisted. “Need a guide, friend?”

“Я не хочу,” I said, and it seemed to work. Russian has always been my favourite go-to language for confusing street hawkers.

Reaching the park, I found – as I’d feared – that it was indeed guarded by men with guns. There were barricades around the lawns, and though, by peeking through a gap, I could make out what looked like the beginning of an old stone culvert, there was simply no way of getting inside. I scouted around the Parque Independencia, eyes on the barrier, looking for an entrance – but the place was on lock-down. Another failure.

Passing back the way I had come, the same voice called out to me from the doorway.

“Вам нужен гид, друг?” he called, and I couldn’t help but smile. Fair enough, I thought, he got me. I turned to face him – a young man with an afro, dressed in a grey silk shirt many times too large for his body. He had a hefty, leather-bound Bible tucked under his arm. He said something else in Russian, something I didn’t understand; but then he saw my lost look, and realisation dawned on him.

“I get it,” he said, in English. “You were playing with me – very funny. I’m Isaac,” he added, thrusting out his hand for me to shake it. “What do you want to see here in Santo Domingo?” Isaac was well spoken, and had something of an academic air about him; but when he offered to give me a friendly tour, I knew he was looking for money. It seemed like everyone in this city was.

As if he were reading my thoughts, he quickly said: “No money. No charge. I just like to show people around my city. Come on, I’ll take you for a walk. I know everyone here, you’ll see.”

Isaac looked at me hopefully, and shuffled his Bible from one armpit to the other where it was immediately lost in the folds of his oversized shirt.

I decided to take him up on the offer; I think by now I was simply curious to watch the con unravel, to see at which point he went back on his word and started asking me for cash. I had already given money to several beggars since arriving in the Dominican Republic, but it was hot, I was tired, and I didn’t like being lied to. The whole set-up felt patronising, even down to the Bible tucked under one arm like a trust-me prop.

So I smiled sweetly at him and said, “Yes – I’d love to have a free tour of your city.” I’d even buy him dinner, I thought to myself, if the tour was good; but as Isaac himself had suggested, there would be no money changing hands here.

The tour itself was predictable and rushed. “This statue is a famous symbol of our city,” and then, “there’s the house that Columbus used to live in.” These were all sights I’d taken in within my first half-hour on the streets of Santo Domingo. Soon enough though, my guided tour took on a darker edge.

“See that red sign down there?” Isaac asked me, pointing into a back alley. “Number-one sex club in Santo Domingo. You want to get a girl? A boy, even? I know the owner, I can introduce you.”

I frowned and nodded to his Bible. “I’m not sure Jesus would approve of that,” I said.

Isaac went quiet for a while after that, before switching back to safer recommendations: souvenir shops, churches, and the best seafood in this quarter of the city. We finished up somewhere near my hostel, and I told him I had to go.

“But wait,” he said, stepping into the shadows of a doorway. “You’ll give me a tip, perhaps. Let’s say… thirty dollars?”

“You said no money,” I replied.

“But a tip. That’s all. Just ten dollars maybe, come on.”

“I can’t,” I said, “I’ve got to go – but thanks for the free tour.”

As I turned to leave, Isaac suddenly grabbed my arm. “Give me ten dollars now,” he hissed, angrily.

“No,” I said, and then for good measure, added: “God bless.” He did not pursue me.

Just near my hostel, I passed a man sat in a doorway asking for money. I dropped a 500-peso note into his pot – about $10 – and retreated to my accommodation happily, with a sense as if of some divine karma having been satisfied.

 

Singapore

I never actually planned to go to Singapore, either. As it was, I had a flight from Istanbul to Melbourne with a suggested six-hour wait at Singapore’s Changi Airport. Six hours seemed pretty pointless though, too long to wait, too short to enjoy; and so I shuffled the booking to knock it up to 14 full hours in a city I’d never been to.

There’s a lot you can do in that sort of time. I recently shared a post about my 12-hour visit to Serbia… which couldn’t have gone much better, all things considered. Another time, I paid a visit to Auschwitz on a nine-hour stopover in Poland. Meanwhile my article about urban exploration in Manchester – featuring drains, rooftops and abandoned WWII air raid shelters – was based on the events of one evening, perhaps just six hours in total.

I was perfectly optimistic then, that I had every chance of seeing something incredible during my 14 hours in Singapore.

Getting to the airport, passing through security, I was given an arrival card. ‘Welcome to Singapore’ it said on the front, alongside the city’s crest. I turned the card over; ‘DEATH FOR DRUG TRAFFICKERS’ was printed on the back in large, aggressive red lettering.

Fortunately, I had no drugs on me; the threat did not apply. But still it left me with a vaguely uneasy feeling. It’s hard to be at ease with someone who just threatened to kill you. They weren’t kidding, either: according to Amnesty International, between 1991 and 2004 Singapore had the highest execution rate in the world – 400 hangings.

It’s not only the import of hard drugs that will earn you a tough sentence in Singapore, though. In 1994, an American teenager was punished with caning for spraying graffiti on a wall. You can go to gaol for bringing chewing gum into the country. It’s a $1,000 fine for dropping litter. I had read that making anti-religious statements in public is punishable as ‘sedition’; and that saying nice things about someone who later turns out to be a criminal is charged as ‘abetment.’ Even failing to flush a toilet incurs a public caning, and apparently there are police officers who conduct random toilet checks to inspect your restroom etiquette.

Needless to say, I didn’t plan on doing any of these things – but the more warnings I read, the more paranoid I became about the possibility of landing in trouble by mistake or misunderstanding.

In Singapore, you can be sent to prison for hugging someone who doesn’t want to be hugged. Jaywalkers might receive a fine of $1,000, or up to three months in gaol. Perhaps most applicable to me, connecting your laptop to an unsecured wifi network is considered ‘hacking’… another punishable offence.

My plan for the night was to tour the city with a local. I’d put a message up on a Singaporean web forum, posting an offer to anyone who might accept it: show me the highlights of Singapore in one high-speed, overnight visit, and I’ll buy you dinner.

I had a reply back from Jon, a student at Singapore University – and to his credit, he was the most gracious host I could have hoped for. Although, having said that, there were some places he simply wouldn’t take me.

We met at the MRT station near his apartment, where Jon asked me what I wanted to see and do during my one night in the city. I reeled off a list of things that I’d been researching – the abandoned Changi Hospital, some WWII-era tunnels and the largely now exhumed Bidadari Cemetery. “And a cocktail bar,” I added, “I really want to drink a Singapore Sling in Singapore.”

Jon looked at me quietly for a while. “You have very dark thoughts for someone with such a bright face,” he said at last.

In the end, we spent that whole night walking around Marina Bay. It was a compromise, I guess, and even though it wasn’t exactly what I’d hoped for I was still experiencing a new city for the first time.

By the time we entered our third shopping centre of the evening, it was becoming painfully clear to me that the two of us had very different concepts of fun; but I didn’t want to offend Jon, who had kindly given up an evening to be my guide. Besides… given what the Singaporean authorities will do if they catch you chewing gum, I had no intention to go off trespassing through abandoned hospitals on my own there.

We passed by Clarke Quay, one of the more popular drinking spots in the city. It was a mass of saturated colours, red, yellow and blue spotlights illuminating canvas awnings, noisy beer gardens and the black waters down below. This being a Saturday night, the place was more than busy. Students crowded around trays laden with plastic shot glasses. Chart r’n’b music blasted out of speakers mounted the length of the quay. I had been hoping for something a little more relaxing.

I suggested to Jon that maybe we could grab a couple of beers, sit somewhere quiet at the edge of the water and drink them there. Jon shook his head.

“Not possible,” he said, “here it is illegal to drink alcohol on the street.” (Later I’d find out that this was not strictly true – I guess Jon had been misinformed on that subject.)

We stopped off next near the Merlion: a half-lion, half-fish sculpted fountain positioned on the edge of the bay. This mythical creature has become an unofficial emblem of Singapore, and finally, I felt as though I was seeing something authentic… something that I wouldn’t have been able to see in virtually any modern urban centre anywhere in the world. I asked Jon about the meaning of this mythical creature, but he only laughed.

“It doesn’t mean anything,” he said. “It’s not Singaporean – there’s nothing historic about it. The Singapore Tourism Board just invented it in the sixties, trademarked it, then used it to sell souvenirs.”

After that we kept on walking. Around the bay, over the Helix Bridge, past the bold white flower of the ArtScience Museum, beneath the glittering towers of the Marina Bay Sands hotel. We visited the Supertree Grove as well, an installation of giant artificial trees as much as 50 metres in height, fitted with vertical fern gardens, solar panels, air filtration systems and various other environmental functions. It was an innovative blend of technology and style, though ultimately it left me with one crucial question… Why?

The architecture of Singapore is just fantastic – even better to see its coloured lights mirrored in the waters of the bay – but at the same time, I found there to be something rather soulless about it all. In many ways it felt like glamour for glamour’s sake. I have heard Singapore described as ‘a playground for the rich,’ but from what I could see this playground didn’t really have anything to play on – only flashing slots in which to deposit your money.

Meanwhile the constant barrage of prolific, red prohibition signs – ‘no skateboarding,’ ‘no sleeping here,’ ‘jaywalking is illegal,’ ‘non-smoking area’ – served as a constant reminder of the city’s harsh authoritarianism; even when they referred to activities I hadn’t been planning on doing anyway. I’d also realise, later on, that in all that time I hadn’t seen a single homeless person. No beggars, no tramps, no one who might have tarnished the visual integrity of this carefully managed city-state. Begging in Singapore, apparently, incurs a $3,000 fine.

Dawn arrived, I made my farewells to Jon and I headed back to the airport. Singapore had been interesting, but that was enough for me. It felt like a city too much focussed on appearances – flashy, purposeless towers, beautiful high-tech gardens, even shopping centres fitted with indoor canals – but for all that, it seemed to lack a heart. We spoke to various people throughout the evening, but none of them were from here. From my experience of the place, it felt more transitory, like a flashy university campus or an airport departure hall.

Speaking of which, Singapore Airport is a wonder in itself. The place features a butterfly garden, cinemas, games rooms and galleries. On the top floor of the terminal, doors opened outside onto a terraced cactus garden.

I settled down to wait for my flight, was about to get online… then I remembered that accessing unsecured networks was considered a criminal offence here. There was a porter passing, so I asked him which network I ought to be on.

“You shouldn’t sit here,” he said, and I braced for a telling-off… but I’d misjudged. “You should try sitting over there by the bar, the chairs are more comfortable and the wifi signal is stronger.”

So I did. I caught up on some emails, then strolled through the terminal’s orchid gardens. I had a look at some cultural exhibits, had a shower, breakfast, and even treated myself to that Singapore Sling in the end. I could have just stayed in the airport all along, I thought to myself.

 

The Bahamas

Another one of those stopovers – this time, 12 hours. I was flying from Miami to Havana, a distance of just 230 miles, though frosty US-Cuba relations served to make that short journey far more complicated than it ought to be. My solution was to change planes in the Bahamas, touching down overnight in the capital, Nassau.

The flight out of Florida was on one of those tiny craft you sometimes see in old movies, the type with propellers and great big clunky engines that hang from the bottom of the wings, shuddering like overripe fruit. I would have spent the flight staring out the window at the engine, wondering how long before it dropped off, if I hadn’t found myself engrossed in conversation – thankfully – with the man seated next to me.

He was Syrian, a businessman, on his way to the Syrian embassy at Santo Domingo to deal with a land feud on behalf of his family back home. The family property had been caught up in the war, and during that short flight I learned a huge amount about the effect the conflict was having on regular Syrian people. That flight would prove to be the most interesting thing about my whole trip to the Bahamas.

We arrived shortly before midnight.

Here was my plan: I was tired, I’d already heard that prices would be sky-high, and so when I cleared security I’d find a quiet corner of the airport and get a few hours’ sleep. Three hours ought to do it, then I would find somewhere to leave my heavy bags and by 4am I’d already be in Nassau. After that, I had no idea what came next – but I’d have six hours to do something. Maybe I would simply walk the streets, admire the colonial architecture. Perhaps I’d stumble across some beautiful ruin in the backstreets, or spend my morning exploring public parks. Either way, it would only be a few hours before the sun came up over New Providence and then I’d take a few photos, grab a quick breakfast and be back at the airport with time to spare.

That was the plan, at least; but here’s how it actually went down.

I took my bags, I found a quiet corner of the airport and prepared to go to sleep. Barely had I closed my eyes when I felt a hand on my shoulder.

“Sir,” he said, “I’m going to need to see your boarding pass.”

There was a burly airport police offer stood over me, ready to shake me awake. I noticed the gun at his belt.

“Sir, what time is your flight?”

I told him I had a flight in the morning, and he shook his head.

“You can’t sleep here. The waiting area is reserved for passengers flying tonight.”

So, it looked like I had to advance the plan. Sleep would have been nice, but I knew I’d cope without it. I asked the officer if there was somewhere I could leave my heavy bags.

“No,” he said, “you need to stay in a hotel.”

“How far is the beach?” I asked.

“You need to stay in a hotel,” he replied.

“Would there be somewhere in Nassau I could leave my bags overnight?”

“You need to stay in a hotel,” he said again, as if he were broken, and then suddenly he was marching me – not gently – towards a tourist information desk.

“This gentleman needs a hotel room and a taxi,” he told the clerk at the desk.

They should change the marketing for this place, I was thinking. The Bahamas: where men with guns frogmarch you to paradise. It was awful.

The young man at the desk had brought up the details of a hotel on his screen, and was already reeling off the various benefits included.

“…flat-screen TVs, full climate control, spa membership, private beach access, a range of evening entertainments…”

I glanced down at the price – $349 a night.

“I have 10 hours until my flight,” I told him. “The only thing I’m likely to see is the bed.”

“You need to stay in a hotel,” said the malfunctioning police officer.

“Fine,” I said. “Alright. What’s the cheapest hotel you’ve got?”

The clerk started reeling off the various USPs of the something-or-other-resort-and-spa-complex: “…high-speed wireless Internet, free use of sun loungers and parasols, in-room safe boxes and mini-bar, complimentary spa robes…”

“I have 10 hours until my flight,” I interrupted him.

“You need to stay in a hotel.”

“How much?” I asked.

“One hundred dollars.”

Fine, whatever, I thought. I didn’t seem to have a lot of choice in the matter. The armed police officer stood watching me while a taxi was called, even escorted me to the car… as if I might run off at any moment. This whole experience was possibly the least friendly welcome I’ve ever had to any country. North Korea beats the Bahamas by a mile, when it comes to hospitality. I wondered if airport security took a commission on last-minute hotel bookings.

After I was bundled into the car like a naughty child, I asked the driver if there was anywhere nearby that might charge less than $100 to look after my bag while I explored.

“Sure, boss,” he said. “There’s a place they’ll do you a bed for $70.”

Okay, I thought, it’s a start.

“Only thing – that one’s way out past Nassau,” the driver explained. “I’ve gotta charge you $20 extra to get you there.” Which would no doubt mean adding on an extra $20 in the morning, too. I may as well just stick at a hundred, I decided.

Arriving at the hotel – a cute, ramshackle affair of painted wooden gables, ferns and palms and garden candles – I passed a sign that hung above the door. ‘Fawlty Towers, Nassau,’ it read. It was funny; I felt a positive feeling creeping through me, and for a moment I decided that perhaps, just maybe, this was going to be alright.

I found the desk and asked them what they had available.

“Only thing we’ve got is a villa,” the lady told me. “It’ll be $140 for the night.” and just like that, my positive feeling evaporated. I asked if it might be possible just to leave my bags at the place and pick them up in the morning. I’d pay a fee, I told them.

“Sure,” the lady said. “I’ll just need your credit card first, then you’re welcome to leave your bags in your own villa while you’re out. It’ll be $140.”

The Bahamas and their enforced luxury had won. I was here now and there was no point trying to hike into the city with two heavy travel bags strapped to me. I gave up, gritted my teeth, and slid my bankcard across the counter. Including taxi fares, I had just paid $180 for a waiting room.

It was almost 3am by the time I’d finished checking in, and dragged my bags to the private sea-view chalet that rose up on stilts above tropical bushes. It was too late to go anywhere else… and there was absolutely nothing to do here, it seemed, but look at the sea, walk on the sand or sit by the pool drinking $30 cocktails.

I read a book until falling asleep, and later woke up to the sound of crashing waves. Outside, the beach was clean and empty – only small wooden huts scattered along the headland, palm trees jutting out from the sand here and there as the beach folded gently into the clear waters of the Caribbean. There were no monuments, no ruins, no cemeteries or museums, no history, no street life and no architecture, save for the simple wooden panels of private villas painted up in all the colours of the rainbow. I may as well have been in purgatory.