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Explore Moldova’s wine heritage and Transnistrian history in one full-day guided tour featuring the world's largest underground winery and Tiraspol’s unique charm.
A Complete Day of Moldova’s Charm: Milestii Mici Winery and Tiraspol Fortress Tour Review
This full-day tour from Chisinau combines two of Moldova’s most intriguing destinations—the massive Milestii Mici winery and the unofficial capital of Transnistria, Tiraspol. Offering a blend of impressive underground wine cellars and Soviet-era history, the experience promises a fascinating look at Moldova’s cultural and historical layers.
What really draws us in is the chance to visit the world’s largest underground wine cellar—home to over 2 million bottles—and to explore Tiraspol, a city that feels like a step back in time with its Soviet architecture and fortress ruins. The tour includes guided wine tastings, hotel pickup, and round-trip transport, making it relatively hassle-free for travelers wanting to maximize their day without stressing about logistics.
However, a consideration for travelers is that the itinerary hinges partly on the winery’s power situation, as one review noted a temporary closure due to electricity issues. If you’re someone who loves a good story about overcoming obstacles or simply enjoys a well-organized trip, this may influence your decision.
This tour suits those eager to see Moldova’s hidden gems, especially if they’re interested in wine, history, or unique cultural experiences. It’s also ideal for travelers who prefer small-group tours for a more personalized touch and appreciate a knowledgeable guide to deepen their understanding.


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Most travelers will find the hotel pickup smooth and punctual, with reviews indicating guides like Dmytro and Natalia are friendly, professional, and eager to share their knowledge. We loved the way the small group size (max 18) encourages a more intimate experience, allowing for personalized attention and plenty of opportunity to ask questions.
The drive from Chisinau is about 30 km (roughly 20 miles)—a short, scenic ride that gets you into the heart of Moldova’s wine country. The temperature in the underground cellar is kept between 54-58°F (12-14°C), which, as one reviewer noted, is ideal for preserving the natural aroma of the wines.
Once inside, you’ll be awestruck by the sheer scale of Milestii Mici. The cellar stretches over 200 kilometers underground, with over 2 million bottles stored in the Guinness Book of Records. You’ll walk through the underground streets, feeling like you’re on an adventure through a subterranean city.
One reviewer, Mark S, described the experience as “boggling” and appreciated the guided walking tour that showcases the “Golden Collection”—the most valuable bottles, some with vines still attached. You’ll also visit the cellar store, where you can buy a bottle directly from the heart of the winery. We loved the detailed explanations from guides like Nathalia, who makes the history and process come alive.
The tour includes two wine tastings—a highlight for many. The guides emphasize the aroma and character of the wines, and you’ll get a chance to savor some unique Moldovan varieties. Several reviews noted that guides are very knowledgeable, allowing guests to deepen their appreciation and ask about specific wines.
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One notable review mentioned a power outage that temporarily closed the underground cellars, a reminder of Moldova’s unpredictable infrastructure. While disappointing in the moment, the guide handled the situation seamlessly, and the day was still memorable. This highlights the importance of flexibility and understanding when adventuring off the beaten path.
After lunch (which is not included but can be arranged at local restaurants), the tour heads to Tiraspol, the de facto capital of Transnistria. Founded after the Peace Treaty of Jassy, the city has a distinctive Soviet vibe, with Suhorov microdistrict and remnants of fortress walls. The main attraction here is the Saint Vladimir powder vault, now housing a local fortress exposition and a church.
The journey to Tiraspol offers a window into post-Soviet Moldova, with many reviewers mentioning how the city feels like stepping into a different era. One travel enthusiast called it “a city that feels like a living museum of the Soviet era,” and that’s exactly what makes it an interesting contrast to the wine tour.
If you wish, the guide can recommend some of Tiraspol’s best restaurants, perfect for a relaxed meal after sightseeing. This is an excellent opportunity to reflect on the day and enjoy local cuisine.

Given the $207.28 price per person, this tour offers strong value, especially considering the guided tours, transportation, and tastings included. The small-group format enhances the overall experience, making it more engaging and personalized.
While the winery’s temporary closure due to electricity could be seen as a drawback, the overall experience of exploring Moldova’s largest underground cellar and learning about its wine heritage remains worthwhile. The expert guidance and authentic tasting opportunities stand out, as reviews mention guides like Dmytro and Natalia as being particularly knowledgeable and approachable.
The tour balances history, culture, and flavor perfectly, with enough flexibility to include added meals or explore on your own after the main sites. The round-trip transport from Chisinau simplifies planning, making it ideal for those who want to focus on the sights rather than logistics.
This experience is perfect for wine lovers eager to see one of the world’s most impressive underground cellars and taste authentic Moldovan wines. It’s also well-suited for history buffs interested in Soviet-era architecture and adventurous travelers keen to explore Moldova’s lesser-known regions.
Travelers expecting a luxury experience might find the tour more modest but authentic and highly informative. If you’re comfortable with small-group tours and enjoy guided walks, this will be a highlight of your Moldova trip.

This tour balances wine, history, and culture, offering a comprehensive glimpse into Moldova’s unique identity. The guided insights make it especially valuable, turning a simple visit into a memorable educational experience. While some may wish for a longer winery visit or more free time, the overall package presents a fantastic way to see Moldova’s best-kept secrets in one day.
If you’re looking for an authentic, educational, and fun way to spend a day outside of Chisinau, this tour provides both value and a chance to experience Moldova’s most iconic sites.
Is hotel pickup included in this tour?
Yes, the tour offers hotel pickup and drop-off, making it convenient to start your day without worrying about transportation.
What is the tour duration?
The entire experience lasts approximately 8 hours, including travel, sightseeing, and tastings.
Are children allowed on this tour?
Children must be accompanied by an adult. The tour is designed for general travelers and typically suitable for families.
What should I bring for the tour?
Bring your passport (necessary for crossing into Transnistria), comfortable walking shoes, and a camera. Lunch is not included, so consider bringing snacks or eating before or after the tour.
Will I get to buy wine during the tour?
Yes, the visit includes a specialized wine shop where you can purchase bottles directly from the winery.
Can I participate if I don’t drink alcohol?
While the tour includes wine tastings, you are free to decline tasting if preferred. Guides are happy to accommodate.
What happens if the winery is closed due to power issues?
In case of unexpected closures like power outages, the guide will adjust the schedule, and you may spend more time exploring other areas or visiting Bender or Tiraspol.
Is this tour suitable for most travelers?
Yes, most travelers can participate, though those with mobility issues should consider walking distances underground and around the city. Most travelers will find it accessible and engaging.
Whether you’re a wine aficionado, a history enthusiast, or simply curious about Moldova’s diverse culture, this tour offers a well-rounded, memorable day that combines the best of what the country has to offer.