Chisinau is a surprisingly lively city, offering more than just Soviet-era architecture and vineyards. Its real charm lies in the stories and experiences you can uncover through thoughtfully curated tours. For example, visiting Transnistria with Anton Dendemarchenko (see tour here) offers a glimpse into a region where the Cold War never really ended. Or, for those with a taste for wine, the Cricova Winery & Old Orhei Tour (details here) combines underground cellars with ancient archaeological sites. Whether you’re interested in Soviet relics, wine, or the unrecognized country of Transnistria, Chisinau’s diverse tour options deliver a memorable experience.
Quick Overview
Chisinau’s best tours span historical explorations, Soviet heritage, and wine adventures. You can choose private, small-group, or full-day excursions, each offering deep dives into Moldova’s unique character. Highlights include Tiraspol’s Soviet monuments, the underground Cricova winery, and the fortified city of Bendery. Below, we explore each of these experiences in detail, helping you decide which fits your travel style.
1. Tiraspol must-see tour with Anton Dendemarchenko – Pridnestrovie
This tour offers a personalized journey through the heart of Transnistria, the unrecognized breakaway republic on Moldova’s eastern border. For around $40, you’ll spend approximately 2.5 hours exploring iconic sites like the Kvint Distillery, tank monument, and House of Soviets. Anton Dendemarchenko’s reviews consistently praise his ability to customize the experience, making it ideal for those seeking an authentic, intimate insight into a place that feels frozen in time. Highlights include the Soviet-era monuments, postcard-worthy squares, and local markets.
What sets this tour apart is its flexible, private format, allowing you to explore at your own pace. The optional virtual tour offers a sneak peek at sites you might not see in person, adding a modern twist. If you’re curious about what life is like in a self-declared republic, this is a must-do.
Bottom Line: An excellent introduction to Transnistria, perfect for travelers who appreciate personal interaction and a focus on Soviet relics.
2. Travel to Pridnestrovie with Anton Dendemarchenko – day tour
For those wanting a fuller picture, this 5- to 9-hour tour provides a comprehensive look at Tiraspol, Bendery, and beyond. At about $115, it includes transport, multiple stops, and a local perspective on the region’s dark and colorful history. Anton’s reviews highlight his storytelling and ability to uncover hidden gems, making this trip a true adventure. Tour highlights include Lenin statues, Soviet architecture, and lesser-known sites for the truly curious.
What makes this tour unique is its interactive approach—riders hop onto trolleybuses and marshrurka vans, experiencing local transit firsthand. Anton’s goal is to show the real country, not just the tourist spots. It’s best suited for travelers who want a deep, immersive experience with a local guide.
Bottom Line: An all-day journey that reveals the unvarnished truth behind Transnistria, perfect for history buffs and inquisitive travelers.
3. Best of Moldova: Cricova Winery & Old Orhei Tour including Curchi Monastery
For around $160, this 8-hour full-day tour combines wine, archaeology, and religious sites. It starts at the famous Cricova Winery, whose tunnels stretch for 120 km—an underground city of wine. As you walk through the labyrinth of caves, you get a detailed explanation of Moldovan viticulture. The tour also includes a visit to Old Orhei, an archaeological complex with ancient ruins and a cave monastery, plus the stunning Curchi Monastery.
Guests frequently praise the wine tasting experience, with reviews mentioning the “exceptional wines” and the chance to sample local specialties. The tour is ideal for history and wine lovers who want a full picture of Moldova’s cultural heritage. Some find the wine portion a bit lengthy, but many consider it excellent value for the comprehensive experience.
Bottom Line: Perfect for travelers who want a mix of history, religious sites, and wine tasting, all in a single day.
4. Chisinau: Discover Soviet Heritage of Transnistria
This 8-hour tour is excellent for history enthusiasts interested in the Soviet era. It emphasizes the architecture, statues, and memorials that define Transnistria’s identity. The tour includes visits to Bender Fortress and walks through Tiraspol’s streets lined with Soviet monuments. Travelers often comment on how this tour makes them feel like they’ve stepped into a museum of the USSR.
A popular feature is the Soviet-style lunch, which immerses you further into the local scene. The reviews are glowing, praising guides like Natasha and Ecaterina for their knowledge and personal stories. This tour is suited for those who want a deep dive into Cold War relics with an authentic local guide.
Bottom Line: An ideal choice for soviet history fans wanting a personal and comprehensive experience.
5. Soviet Era Tour of Transnistria from Chisinau Moldova
At approximately $113, this private 7- to 8-hour tour offers an in-depth look at Soviet symbols. It includes visits to Tiraspol, Bender, and other key sites with commentary tailored to your interests. Guests mention guides like Marcel and Ecaterina, who share personal insights and stories that go beyond the usual script.
The tour features iconic monuments of Lenin, Soviet architecture, and local markets, making it a comprehensive snapshot of the region’s Cold War-era landscape. Its value lies in the personalized approach—you get ample time and attention. Reviewers note how much they learned about the struggles and resilience of this unrecognized region.
Bottom Line: Best suited for travelers seeking a personal, story-driven tour into Moldova’s Soviet past.
6. One day tour in Transnistria
For about $139, this one-day adventure offers a mix of history, culture, and local flavor. Starting from Bendery Fortress to hidden sites, it’s a trip for those who want to see more than just the main attractions. The guide emphasizes showing true local life, with stops at souvenir shops, markets, and authentic eateries.
Guests comment on how the tour feels like visiting a family member’s hometown—relaxed and genuine. It’s perfect if you prefer a less formal, more personal experience that includes the torture museum, Ottoman architecture, and local stories. The reviews highlight the enthusiasm and knowledge of guides like Corneliu.
Bottom Line: Great for travelers who want a comprehensive, personalized day exploring the lesser-known corners of Transnistria.
7. Tiraspol and Bender Back in the USSR Tour
This 6-hour tour is ideal for time-limited visits. It covers Bendery Fortress, Tiraspol’s main Soviet monuments, and local markets. Priced at $110, it’s praised for offering a solid overview with a focus on Soviet memorabilia, including tank monuments and the Palacio Presidential.
Reviewers mention how this tour feels like “a trip to the USSR,” with guides like Nicolai and Laurentina bringing history alive through stories and site visits. It’s suited for travelers who want a compact but thorough snapshot of the region’s Cold War relics. Some may find the pace quick, but the value for a half-day adventure is clear.
Bottom Line: An efficient, fun introduction to Soviet Moldova for those short on time.
8. Best of Chisinau City Tour
This 3-hour private walking tour (see details here) makes navigating Moldova’s capital simple and engaging. For only $63, you’ll see Stefan cel Mare Park, Cathedral of the Transfiguration, and the Piata Centrala. It’s perfect for first-time visitors wanting a taste of the city’s highlights.
Reviews highlight guides like Helena and Natalia, praising their local knowledge and friendly approach. The tour is flexible, with options to include presidential buildings and museums based on your interests. It’s well-suited for travelers who prefer a manageable, well-paced overview with the convenience of hotel pickup.
Bottom Line: A great choice for those wanting a short, comprehensive introduction to Chisinau.
9. 1 DAY: Transnistria tour from Chisinau with local guide
This full-day private tour costs about $149 and is perfect for those eager to see the region in-depth. It includes border crossing, visits to Tiraspol, Bendery Fortress, and local markets. The guide Liliya is known for her knowledge and friendliness, making the journey smooth and insightful.
Guests rave about how the tour “exceeded expectations,” appreciating the personalized attention and insider stories. It’s ideal for history buffs or travelers who want a detailed portrait of Transnistria’s political and cultural landscape. The tour’s flexibility allows you to tailor stops, making it a full immersion experience.
Bottom Line: Perfect for travelers wanting a complete, personalized day exploring Moldova’s mysterious eastern neighbor.
10. Back in the USSR – Transnistria
At around $113, this 8-hour tour offers a classic Soviet experience. It includes Bender Fortress, Soviet monuments, and the tank park. The guide Oleg, praised in reviews, shares detailed stories about the region’s past, making history tangible.
The tour appeals to history enthusiasts and Cold War fans, with visits to Lenin statues, Soviet government buildings, and monuments to the Afghanistan War. Reviewers mention how the tour feels like “a trip into a different era,” with plenty of photo opportunities. It’s suited for travelers wanting an authentic, story-rich experience.
Bottom Line: A solid, story-driven tour for soviet history lovers.
11. Return to the USSR – Excursion in Transnistria
For $120, this private 7-hour tour offers a comprehensive look at Bender, Tighina, and Tiraspol. Highlights include medieval fortress walks, Soviet monuments, and local markets. Guides like Natalia and Nicolai are noted for their detailed commentary and personal stories.
Reviewers mention feeling like they’ve traveled back in time — especially when visiting Lenin’s house and Soviet memorials. The tour is best for those who enjoy historical details and relaxed pacing.
Bottom Line: An excellent, personal introduction to Moldova’s Soviet side.
12. From Chisinau: Old Orhei complex and Cricova Wine Tasting
This tour (see details here) offers a full-day experience blending archaeology and wine. Starting at Old Orhei, a complex with ancient ruins and cave monasteries, then visiting Cricova’s underground tunnels, it covers Moldova’s cultural and viticultural highlights.
Guests rave about the wine tasting, with many describing the underground city as “unlike anything else.” The lunch in rural villages adds an authentic touch. The tour is ideal if you want a balanced mix of history and relaxation. It’s particularly good for those who enjoy local food and wine.
Bottom Line: A well-rounded day for history, wine, and scenic landscapes.
13. Highlights of Moldova – 3 destinations in 1 day-Small Group Tour
This private, customizable tour (details here) allows you to select Curchi Monastery, Cricova Winery, or Old Orhei. Priced at $125, it’s perfect for travelers wanting flexibility.
Guests appreciate the personalized itinerary and the ease of transportation. Guides help tailor the day to your interests, making it suitable for family groups or solo travelers. Its highlight is the ability to combine cultural, spiritual, and wine experiences in one day.
Bottom Line: Best for those who want control over their schedule and a personalized experience.
How to Choose the Right Tour
The key to picking the best tour depends on your interests, time, and budget. If you’re passionate about Soviet history, tours like Discover Soviet Heritage of Transnistria (see tour here) or Back in the USSR (details here) are perfect. For wine lovers, the Cricova and Milestii Mici (see details here) offer immersive tastings with underground cellar tours.
Those seeking a flexible, personalized experience should consider private or semi-private options like the Pridnestrovie day tour or the Highlights of Moldova (see tour here). Budget travelers might prefer the city tour or a half-day Soviet heritage walk. Make sure to book early, especially in peak season, to secure your spot.
Final Words
Chisinau offers a surprising array of tours that cater to different interests—whether you want to explore Soviet relics, sip Moldova’s finest wines, or see the unrecognized country of Transnistria. For a personalized, deep experience, private tours like Anton’s Pridnestrovie excursions are unbeatable. If time is tight, the short city tour is a smart choice. And for those with a passion for history or wine, the full-day tours provide immersive insight.
No matter your preference, these options are worth booking in advance—many travelers find that early planning makes all the difference in Moldova’s unpredictable weather and busy season. So pick your adventure, and get ready to uncover a side of Moldova few travelers ever see.