When visiting Chisinau, Moldova’s lively capital, you’ll find a city bursting with surprises — from Soviet-era relics to world-class wineries. What makes Chisinau stand out is its blend of history, culture, and authentic local flavor, often accessible through well-organized tours that go beyond sightseeing. We especially love the Back in the USSR – Tiraspol & Bender City for its nostalgic trip back to Soviet times, and the Cricova underground Winery & Old Orhei Archaeological Complex which combines Moldova’s famed wine culture with ancient history. These experiences give travelers a real taste of Moldova’s multifaceted identity, all in engaging, memorable formats.
Quick Overview
Chisinau offers a fantastic range of guided tours, city walks, historic site visits, Soviet heritage explorations, and wine tastings. Whether you want to walk through the city’s main sights (Best of Chisinau City Tour), explore the breakaway Transnistria with its Soviet relics, or indulge in Moldova’s celebrated wine culture (Mileștii Mici wine tour), there’s something for every interest and schedule. Below, we detail the top options, highlighting what makes each one special.
1. Chisinau: Discover Soviet Heritage of Transnistria
At number one, this 8-hour tour offers an immersive experience into the Soviet legacy of Transnistria—an unrecognized country that still operates with Soviet symbols. Explore Communist-era buildings, Lenin statues, and memorials in Tiraspol and Bender. Highlights include visiting Bender Fortress, an important 16th-century site, and enjoying a Soviet-style lunch with recipes from that era. The walking tour in Tiraspol reveals the city’s Soviet architecture and monuments, making it a perfect choice for history buffs or those curious about post-Soviet space. The tour’s reviews praise the knowledgeable guides and the authentic experience of stepping into a country that doesn’t officially exist, making it a truly unique adventure. Bottom line: ideal for anyone interested in Cold War history or looking for a memorable day outside the usual tourist circuit.
2. Soviet Era Tour of Transnistria from Chisinau Moldova
This private 7 to 8-hour tour provides a comprehensive dive into the Soviet symbols still present in Transnistria. Starting from your hotel in Chisinau, you’ll cross into the breakaway territory, where Lenin statues, Soviet architecture, and tanks in the city center transport you back to a different time. Visitors rave about guide Marcel’s deep knowledge and friendly demeanor, and many mention the visit to Tiraspol as a highlight. The tour also includes optional visits to wineries like Milestii Mici or monasteries for a small extra fee. It’s perfect if you want a private, flexible day with detailed historical insights. Bottom line: excellent for those wanting a personalized story about Moldova’s complex relationship with its Soviet past.
3. One day tour in Transnistria
For around $139, this 7-8 hour excursion is a well-rounded introduction to Transnistria. It begins with exploring Bendery Fortress, a 16th-century Ottoman site, and continues with a walk through Bendery city, home to Russian-inspired architecture and a torture museum. The tour then moves on to Tiraspol, where you’ll see the largest Lenin monument in Moldova and the tank monument, which is a must-see for Soviet memorabilia fans. Tour guide Anna is praised for her local knowledge and warm approach. This tour suits travelers looking for a full day of history, military sites, and local color. Bottom line: a balanced, engaging trip perfect for history enthusiasts.
4. Best of Chisinau City Tour
If you prefer to stay within the city, this 3-hour private walking tour covers the highlights of Chisinau. Visit Ştefan cel Mare Park, the Cathedral of the Transfiguration of the Saviour, and the Piata Centrala—the main market—giving you a taste of local life. The guide also takes you to significant government buildings and the Opera House, with personalized commentary tailored to your interests. Reviews mention how this tour makes navigating the city easier and more meaningful, especially for first-time visitors. It’s suitable for those with limited time or who prefer to explore on foot. Bottom line: a great primer for orienting yourself in Chisinau’s cultural and historic landscape.
5. From Chisinau: Old Orhei complex and Cricova Wine Tasting
This 7-hour tour is a favorite among wine lovers and history fans alike. It takes you to Old Orhei, a picturesque archaeological site with ancient ruins and a cave monastery. Afterward, visit the Cricova Winery, known for its 120 km of underground galleries, where you’ll taste local wines and learn about Moldova’s century-old wine tradition. The tour includes a traditional lunch at a rural guesthouse in Butuceni or Trebujeni villages. Reviewers praise the knowledgeable guides and the high-quality wine tasting. This tour balances cultural exploration with delicious local food and drink. Bottom line: perfect for those who want a blend of history, scenery, and wine.
6. Back in the USSR – Tiraspol & Bender City
This 7-8 hour trip visits Transnistria, a place where the USSR is still alive. The tour includes stops at Bender Fortress, a site of historic battles, and walking tours of Tiraspol with visits to Lenin monuments and the house of Soviets. Reviewers highlight their guides’ deep knowledge and the immersive experience of seeing Soviet symbols still prominently displayed. It’s especially suited for travelers interested in Cold War relics and unique political histories. Expect to see tanks, military memorials, and authentic Soviet architecture. Bottom line: an eye-opening trip for those curious about post-Soviet geopolitics.
7. Transnistria Tour from Chisinau Explore Soviet Time Capsule
At around 7 hours, this Soviet-focused tour captures Transnistria’s atmosphere with visits to Bender Fortress, Tighina, and Tiraspol’s main sights. The guide Ana shares insights into the region’s history and current reality, making it ideal for travelers who want to understand this geopolitical curiosity firsthand. Reviews commend the knowledgeable guides and smooth logistics. This is a compact, well-organized way to experience Soviet relics, and the tour’s flexibility makes it suitable for those with limited time but strong interest. Bottom line: an informative, engaging snapshot of Moldova’s Soviet leftovers.
8. Chisinau: Cricova Wine tour & Old Orhei Archaeological Complex
For a full day of experiences blending history and wine, this day trip combines visits to Old Orhei and the Cricova Winery. Travel through the scenic countryside, explore ancient ruins and caves, and enjoy a wine tasting session. Guests rave about the guides’ knowledge and the delicious local cuisine. It’s perfect if you want an immersive day out, with a good mix of outdoor exploration and relaxing tastings. Bottom line: a comprehensive experience suited for those wanting to see Moldova’s rich past and taste its best wines.
9. Chisinau Walking Tour with Local Guide
This 2.5-hour private walk offers a relaxed way to see Chisinau’s main sights, from Stephen the Great Park to the National History Museum. The guide is praised for tailoring the walk to your interests and sharing personal insights. It’s perfect for first-time visitors wanting a manageable, engaging overview of the city. Reviewers mention how helpful the guided commentary was and how the walk made the city’s sites more meaningful. Ideal for those with limited time or who prefer walking. Bottom line: a personalized city introduction that makes Chisinau accessible and memorable.
10. Cricova underground Winery – with wine tasting
For a luxury experience, this private tour includes a visit to the Cricova underground cellar. Explore multiple locations, roam the underground tunnels, and enjoy a deluxe wine tasting with snacks. The guide facilitates a customized experience, making it perfect for wine connoisseurs or those celebrating a special occasion. Visitors comment on the impressive tunnels and high-quality wines. It’s more intimate and refined than standard tours, fitting well for adults seeking exclusivity. Bottom line: a memorable, upscale wine journey with personalized attention.
11. Old Orhei & Curchi Monasteries in One Day
This 5-6 hour private tour combines Old Orhei’s archaeological ruins with the serene Curchi Monastery. Travel comfortably from Chisinau and enjoy guided visits to both sites, with insights from your guide. Guests love the smooth logistics and the chance to experience Moldova’s spiritual and historical sites in one day. It’s excellent for travelers wanting a balanced mix of outdoor history and religious architecture, with plenty of opportunities for photos and reflection. Bottom line: a well-rounded cultural day trip for history and religion enthusiasts.
12. Chisinau: Discover City Highlights with a Walking Tour
If you want a quick but thorough overview of Chisinau, this 3-hour private walk is perfect. Covering key sights like the Parliament building, the City Hall, and the Orthodox Cathedral, the tour is praised for its personalized approach. Reviewers mention how the guide’s knowledge enriched their understanding and how the walk made the city’s architecture and history come alive. Ideal for first visitors or those short on time. Bottom line: a concise, informative way to get your bearings in Chisinau.
13. Moldova: Wine tour to Mileștii Mici cellar with Tasting
This 4-hour tour takes you deep underground into Mileștii Mici, the world’s largest wine cellar (with 200 km of tunnels). Taste three different wines and enjoy snacks while exploring the vast underground corridors. The Guinness World Record-holding cellar offers a surreal experience—imagine tasting wine amid limestone walls that stretch for miles. Many reviews highlight the impressive scale and quality of the wines. Suitable for wine novices and enthusiasts alike, it’s a straightforward, memorable experience. Bottom line: an iconic Moldovan wine adventure that is both educational and delicious.
14. Chisinau: Transnistria Soviet Era & Castle Mimi Winery by Car
This full-day tour combines Castle Mimi, a stunning winery, with visits to Transnistria’s Soviet sites. Starting with a guided tour and wine tasting at Castel Mimi, you’ll then explore Bender Fortress and Tiraspol. The luxury vehicle and personal guide ensure comfort and flexibility. Guests enjoy the balance of scenic vineyard views with historical Soviet sites. It’s ideal for travelers wanting a luxurious, all-in-one day experience that combines wine and history. Many reviewers note the well-organized itinerary and engaging guides. Bottom line: great for those who want to combine Moldova’s wine prestige with its Cold War relics in style.
How to Choose the Right Tour in Chisinau
Choosing the best tour depends on your interests, budget, and time. If history and Soviet relics fascinate you, the Back in the USSR or the Soviet Era Tour are excellent options. For a relaxed city experience, the Chisinau City Highlights offers a compact overview. Wine lovers should consider the Mileștii Mici or Cricova tours for their underground cellars and tastings. For those wanting a full day with a mix of outdoor sites, Old Orhei combined with winery visits is a great choice, especially if you prefer guided transportation and local food experiences.
Book tours early, especially in high season, and consider whether you want a private, small group, or large group experience. Some tours include hotel pickup and customizable itineraries, which can make your day smoother.
Final Thoughts
From Soviet relics and hidden monuments to wine tastings and city walks, Chisinau’s tour options are diverse and engaging. For history lovers, the Soviet heritage tours offer a rare glimpse into a world that’s still very much alive in places like Tiraspol and Bender. If wine and archaeology are more your style, then the Old Orhei and Cricova tours deliver memorable experiences in the Moldovan countryside.
Finally, for a quick, friendly introduction to the city, the City Highlights walking tour makes it easy to see the main sights without feeling rushed. No matter your choice, booking early ensures you’ll secure a spot on these popular tours and make the most of your time in Moldova’s capital.