Exploring Moldova: Europe’s Least-Visited Country and Its Unresolved Conflict
November 2008: As part of a two-week journey through the Balkans and the former Yugoslavia, my friend Dan and I spent three days in Moldova. I was particularly excited to visit Europe’s least-visited country, a place I knew little about before arriving, and to explore Transdniestria, its breakaway republic.
Moldova is mostly Romanian-speaking and was once part of the Soviet Union, only claiming independence after its collapse. Since then, it has unfortunately earned the title of Europe’s poorest country, plagued by corruption and organized crime. Due to its strategic location between Eastern and Western Europe and Asia, Moldova has been a hub for smuggling—stolen cars, human trafficking, and even organ trade.
Following independence, Moldova fought a civil war with Transdniestria, a Russian-speaking region bordering Ukraine. The conflict was never fully resolved, leaving Transdniestria as one of Europe’s few unrecognized breakaway republics, backed by Russia.
But not everything in Moldova is bleak. The country was once the top wine producer in the Soviet Union, and today, it remains famous for its high-quality yet affordable wines. While Moldova’s political instability and economic struggles are ever-present, its wine culture, history, and unique geopolitical landscape make it an intriguing destination for those willing to explore Europe’s forgotten corner.

Location of Moldova
Crossing into Moldova: A Midnight Train Ride with Soviet-Era Delays
To reach Moldova, Dan and I took a night train from Bucharest, Romania to Chișinău, the country’s capital. We had booked a sleeping cabin, expecting a smooth overnight journey—until we were abruptly awakened in the middle of the night by border guards at the Moldovan border.
All passengers were ordered off the train for about an hour while the train’s wheels were changed to accommodate the different railway gauge used in former Soviet Union countries. This wasn’t just a technical inconvenience—it was intentional. The USSR had deliberately built its rail tracks in a different size than Western Europe as a strategic defense measure, making it harder for an enemy invasion by train.
Half-asleep and standing outside in the cold, we watched as workers hoisted each train car into the air, replaced the wheels, and lowered them back onto the Soviet-gauge tracks. It was an unexpected but fascinating relic of Cold War paranoia, still affecting travelers decades after the fall of the Soviet Union.

Soviet Era hotel Turist
Hotel Turist: A Soviet-Era Time Capsule in Chișinău
Once in Chișinău, Dan and I checked into Hotel Turist, a Soviet-era relic that had once been the only hotel where foreigners were allowed to stay during Soviet times. Now, it felt like a time capsule, preserving Moldova’s Soviet past in all its drab, utilitarian glory.
The hotel was built with few frills—just concrete, outdated furnishings, and the lingering scent of cigarette smoke. Each floor was manned by a heavy-set woman in a light blue apron with bright orange-dyed hair, a relic of the Soviet-era floor attendants, who had a reputation for strictly monitoring guests. Their drill-sergeant demeanor made it clear—these women were best avoided.
The rickety elevator to the top floor was a metal cage with no exterior door, just large enough for two people, creaking uneasily upwards as a cable yanked it along. Blackouts were random and frequent, plunging the already dim hallways into complete darkness.
But despite all of this—or maybe because of it—I loved it. This was exactly the kind of Soviet throwback hotel I sought out during my travels. Unpolished, gritty, and authentic, it was a perfect introduction to Moldova’s Soviet past.

Drab Interior Turist Hotel
Dodging Corrupt Cops in Chișinău
Dan and I spent our time in Chișinău walking all over town, always on high alert for corrupt police officers looking to shake down foreigners for quick bribes. Moldova’s reputation for police corruption was well known, and we didn’t want to become their next target.
That said, sometimes corruption worked in your favor. A friend of mine had once been caught heavily intoxicated in a park, openly drinking from a bottle of alcohol when a police officer apprehended him, threatening arrest. In most countries, this would have been an expensive fine or a night in jail, but in Moldova, my friend bought his way out with a few dollars’ worth of mixed currencies and the rest of his alcohol. Case closed.
To avoid any trouble, Dan and I had our own strategy—whenever we spotted a police officer, we would immediately cross the street, keeping our distance. We also avoided speaking English within earshot of them, blending in as much as possible to stay off their radar.

Soviet Monument
Nightlife in Chișinău: Mafia Clubs, Strippers, and a Stolen Room Key
During our two-night stay in Chișinău, Dan and I explored the city’s Soviet-era monuments by day and its nightlife by night. True to Moldova’s reputation as Europe’s least-visited country, we saw no other foreigners, and English was almost nonexistent. Still, we managed to navigate our way around, thanks to some quick thinking and a bit of luck.
Fortunately, we had picked up some dress clothes in Belgrade, Serbia, allowing us to pass the strict dress codes imposed by Moldovan nightclubs. Without them, we would have been turned away at the door—something we learned the hard way in other parts of Eastern Europe.
A Mafia-Owned Nightclub?
One of the first clubs we entered was without a doubt run by the mafia. As we stepped inside, we were frisked for weapons by huge, broad-shouldered Romanian bouncers. Inside, electronic music blasted at deafening levels, and the clientele was straight out of a crime thriller—mafia types in luxury suits and sunglasses at night, arriving in blacked-out BMWs and Mercedes. This was a stark contrast to the average Moldovan, many of whom still drove rickety Ladas or, in rural areas, even horse carts.
Scantily clad prostitutes in fur coats lingered near the bar, waiting for the arrival of the wealthy, well-connected men who ran the scene. The atmosphere was pure seediness, and the prices reflected it—drinks were absurdly expensive, another clear sign of a place catering to the wealthy elite and criminal underworld.
Even the bathroom urinals were equipped with small TV screens playing hardcore lesbian porn, a bizarre and unexpected touch. But the most unnerving part was the unwelcoming stares from mafiosos sizing us up. We got the message—this wasn’t our crowd. So, after finishing an overpriced drink, we made a quick exit in search of a more relaxed, down-to-earth place.
A Gypsy Underground Bar and a Stolen Room Key
Unfortunately, our second choice wasn’t much better. We ended up in a dungeon-like underground bar, dimly lit and filled with a strange mix of characters—Gypsy prostitutes, a blend of female and male strippers, and once again, mafia-looking guys in gold chains and tracksuits.
One odd pattern we had noticed in this part of Eastern Europe was that clubs, even those frequented mostly by men, often had both female and male dancers. At some point in the night, the male strippers would randomly appear, much to our confusion.
Things went from strange to problematic when one of the girls stole our room key from Dan and refused to return it unless we paid her $100. Knowing we weren’t about to hand over cash for our own key, I quickly came up with a bluff. I convinced her that we worked for the U.S. Embassy and that if she didn’t return it immediately, our security team would arrest her.
It worked. She reluctantly handed back the key, and we wasted no time getting out of there.
Moldovan Nightlife: An Experience Like No Other
Moldova’s nightlife was an adventure in itself—a world of mafia-run clubs, high-priced drinks, gold-chain-wearing gangsters, strippers of both genders, and shady encounters. While we had come looking for a fun night out, we quickly realized that Chișinău’s after-dark scene wasn’t for the faint of heart.

Police car
Exploring Tipova: A Medieval Cave Monastery in Rural Moldova
On our second day in Moldova, Dan and I hired a taxi to take us to the Tipova Cave Monastery, a medieval Eastern Orthodox site carved into the cliffs of Tipova village, a few hours northeast of Chișinău. The drive took us through rural villages and forest-fringed fields, providing a glimpse into the quiet countryside of Moldova.
Our journey in an old Soviet-era Lada was mostly uneventful—until our driver was pulled over by a corrupt police officer and forced to pay a senseless bribe. It was just another reminder that police extortion was a common occurrence in Moldova, even for locals.
Upon arriving in Tipova, we found an idyllic village with a small river and towering cliffs rising along its banks. These cliffs had been hollowed out by monks in medieval times, creating a network of cave monasteries that once served as places of worship and solitude.
We explored several abandoned caves, once inhabited by monks but now left to time. Others were still active, occupied by modern monks, with basic amenities added to their ancient stone dwellings.
Standing inside the centuries-old caves, looking out over the landscape, it was easy to imagine a time when monks retreated to these remote cliffs for religious contemplation. Tipova felt untouched by modernity, a timeless escape from the rest of the world.

Entering Tipova Village

Tipova Village

Tipova Graveyard

Tipova Mideivel Cave monasteries located in the cliffside to the left of the valley

Tipova Mideivel Cave monasteries located in the cliffside to the right of the valley

Cave monastery currently used by monks

Mideivel Writing by Monks on the Cave Walls

Monk at Tipova Cave Monastery

Tipova Cave Monastery

Tipova Cave Monastery

Tipova Cave Monastery-Abandoned Caves

Me at Tipova Cave Monastery-Abandoned Caves

Tipova Cave Monastery
To Transdniestria with a Trusted Driver
On our last day in Moldova, Dan and I hired the same taxi driver from our Tipova trip to take us into Transdniestria. We trusted him, and his basic English skills made communication easier.
With his help navigating the notoriously tricky border, we hoped to avoid bribe-seeking guards and explore one of Europe’s last Soviet-style breakaway states with fewer complications. Our trip to Transdniestria was set to be another unpredictable adventure.