Moldova Wine Tour: Sip Happens Underground
Overview
Forget Paris. Skip Rome. Say 'no thanks' to Venice gondolas. We're taking you to Moldova – Europe's least visited country, which is code for: no crowds, no rip-offs, just lots of wine and weird fun. Underground cellars so massive you need a car to tour them. A country that technically doesn't exist but takes its Lenin statues very seriously. Fancy wine, beer, and food at 'is this a typo?' prices.
This tour is operated by Smiling Grape Wine Tours SRL which is the contracting entity. Payments will be processed by Smiling Grape Wine Tours SRL.
Why This Tour Exists
This tour exists because someone bet us we couldn't find good wine in Moldova. They were spectacularly, deliciously wrong. We came for the curiosity and stayed for the underground wine cities, the four-generation family cellars, and the grandmother who insisted we couldn't leave until we'd tried her homemade plum brandy. Moldova isn't on most travelers' radars — which is precisely why it should be on yours. We designed this tour to take you beyond the obvious, into the world's largest wine cellar (you'll drive through it), through the time-warp of Soviet-era Transnistria, and into family homes where the wine is older than your parents' marriage.
Weird Facts You'll Learn
The stuff that makes this tour genuinely different.
The Underground Wine City
Mileștii Mici isn't just a cellar — it's a 200km network of underground roads with street signs, traffic rules, and over 2 million bottles. Yuri Gagarin allegedly got so drunk during his visit that he lost two days.
Wine Survived Hitler
During Nazi occupation, locals bricked up entire cellar sections to hide their best vintages. Some chambers weren't rediscovered until the 1990s, containing perfectly preserved pre-war wines.
Putin's Personal Collection
Vladimir Putin maintains a private wine collection at Cricova (yes, really). Angela Merkel does too. The cellars are surprisingly egalitarian about their dictator-to-democrat ratio.
Local Legends & Stories
The tales that locals tell — handed down through generations.
The Gagarin Incident
Cosmonaut Yuri Gagarin visited Cricova in 1966. According to local lore, he emerged two days later, deeply confused about what year it was. The exact details are fuzzy — possibly because everyone involved was also drinking.
The Ghost of Mileștii Mici
Workers swear the tunnels are haunted by a 19th-century limestone miner who got lost and never found his way out. Whether he's still wandering or just enjoying the wine collection is unclear.
Sip Sense: What to Taste
Your cheat sheet to what you'll be drinking.
Fetească Neagră
The 'Black Maiden' — Moldova's signature red. Dark fruit, spice, and a finish that lingers like a good story. Think Pinot Noir's mysterious Eastern European cousin.
Rara Neagră
Translates to 'Black Rare' — and it is. Light-bodied red with cherry notes, perfect with everything from grilled meats to existential conversations about life.
Viorica
Moldova's aromatic white. Floral, honeyed, slightly wild — like if Gewürztraminer went on a gap year and found itself.
Pro Tip
Moldovan wine is sold by the litre. Yes, the litre. Bring an expandable suitcase and zero shame.
Why This Tour is Special
- Milestii Mici — Guinness World Record holder for largest wine cellar (200km of tunnels, 2 million bottles)
- Day trip to Transnistria — a country that doesn't exist
- Cricova Winery — another underground wine city with 120km of tunnels
- Soviet oddities: abandoned Cosmos Hotel, quirky amusement parks
- Bar crawls through Chisinau's craft beer scene
- Free bottle of Moldovan wine per person per day!
Upcoming Departures
28 May 2026
12 spots left
11 June 2026
Only 6 spots left!
25 June 2026
9 spots left
23 July 2026
Sold out
20 August 2026
Sold out
1 October 2026
12 spots left
Tour Itinerary
Arrival Day: Warm-Up Drinks
Arrival in Chisinau: Touch down whenever your airline decides to deliver you.
Check into our perfectly located hotel (translation: walking distance from bars) and take a deep breath: you’ve just arrived in Europe’s least visited country. Congratulations, you’re already more adventurous than 99% of your friends!
Free time: Stroll around the leafy boulevards, grab a sneaky pre-tour beer, or just nap off your flight.
Traditional Moldovan Feast: Think hearty meats, dumplings, rich stews, polenta (mămăligă) and savoury pies (plăcinte), basically carbs with a side of carbs.
Bar Crawl Kick Off: From divey basements with sticky floors to craft beer spots that would make cities such as Portland jealous, we’ll break the ice (and possibly the table) as you meet your fellow revellers. Expect shots of divin (Moldovan brandy) and the first of many blurry selfies.
Overnight in Chisinau.
Guinness World Wine Records
Morning: Stroll through Chisinau for a city tour with a pie and wine snack stop – it's the most Moldovan breakfast possible!
Lunch: a craft beer tasting at our favourite taproom because as balance is important.
Afternoon: visit Milestii Mici, the Guinness World Record holder for largest wine cellar on earth – 200km of tunnels packed with 2 million bottles. It’s like Disneyland for adults, minus the screaming kids.
Evening: dive headfirst into a classic bar crawl.
Overnight in Chisinau, probably dreaming about wine fountains.
The Country That Doesn't Exist
Day Trip to Transnistria (Pridnestrovie): Cross the unofficial border into a country that technically doesn’t exist. Passport checks, Lenin statues, hammer-and-sickle flags—it’s like stepping into a Cold War museum.
City Tour of Tiraspol and Bender: See the House of Soviets, war memorials, and wide boulevards lined with Soviet kitsch. The vibe is weirdly charming—like a postcard from 1983.
Bottle Museum: Over 10,000 bottles of booze from around the world. Expect weird bottles of booze in the shape of animals and Jeremy Corbyn.
Lunch at Back to the USSR Café: This restaurant serves Soviet comfort food: dumplings, cabbage rolls, borscht, and vodka on the side. Nostalgia (and indigestion) guaranteed.
Brandy Tasting at Kvint: Moldova’s most famous distillery, producing brandies smoother than Sinatra. Taste your way through decades-old vintages in a very official setting that quickly descends into giggles.
Back to Chisinau: Another wild bar crawl with the addition of karaoke night—belt out 80s ballads with locals who will 100% outsing you.
Overnight in Chisinau.
Show map
Wine & Weirdness
Morning trip to Cricova Winery, another underground wine city with 120km of tunnels.
Afternoon tour of Chisinau’s Soviet oddities that includes: The abandoned Cosmos Hotel, a brutalist masterpiece turned ghost hotel, a quirky amusement park that feels like a 1980s time capsule and bizarre tower blocks dreamed up by Soviet architects after one too many vodkas.
Evening: discover local taverns and bars, complete with babushkas plying us with pie.
Overnight in Chisinau.
Last Day Shenanigans
Our final day is a surprise event – maybe a countryside feast with accordion players, maybe a visit to a Soviet bunker, maybe something even stranger. Moldova likes to keep us guessing.
Free time to shop for souvenirs: Soviet coins, Lenin busts or a giant suitcase for all the delicious Moldovan wine to take home.
Farewell dinner – one last banquet of food, drink and toasts that get more heartfelt with each glass. Expect laughter, nostalgia and maybe even a drunken pledge to move to Moldova.
End of tour but definitely not the end of stories you’ll tell for years...
What's Included
What's Not Included
Practical Info
Getting There
Fly into Chișinău, Moldova’s delightfully underappreciated capital city. It’s surprisingly easy to reach from across Europe and considerably less stressful than airports where people sprint while holding £9 sandwiches. We will handle the wine part from there 🍷
What to Pack
Comfortable shoes, an open mind and trousers with a forgiving attitude toward long lunches. Layers are useful too. Moldovan weather can occasionally behave like a man arguing with a satellite dish. You do not need: fancy wine knowledge, a beret or the ability to describe wine as “having notes of oak and unresolved childhood tension”
Best Time to Visit
Spring and autumn are glorious. Summer is sunny and vineyard-perfect. Winter is all candlelit cellars, heavy food and “just one more glass” becoming a legally binding decision. Honestly, Moldova is dangerously good year-round.
Good to Know
Moldova is one of Europe’s least visited countries, which means: fewer tourist traps, more genuine experiences and locals who still seem pleasantly confused that anyone travelled internationally just to drink wine with them. Expect huge hospitality, generous pours and at least one moment where a grandmother silently places more food in front of you despite your body clearly filing formal complaints.
This Tour is Perfect For
Solo Travellers Welcome
Many guests join Tipple Tours on their own. Small groups mean it rarely takes long before strangers start feeling like travel companions.
Perfect for Friends & Couples
Tipple Tours are even better when shared. Our tours are designed for relaxed conversations, long dinners and plenty of shared travel stories.
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From
£600
per person
Deposit: £99
Private room available: +£200
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Questions About the Moldova Tour
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