5 DAYS:Moldova, Transnistria and Romania 3 countries in one trip!

Exploring Moldova, Transnistria, and Romania in just five days might sound ambitious, but this tour makes it entirely doable—and fascinating. From underground wine cellars to UNESCO monasteries and Soviet-era museums, you get a well-rounded glimpse of these diverse regions.

What we love most about this experience: the variety of places covered, the small group setting that ensures personalized attention, and the inclusive meals and transport that make the trip feel smooth and well-organized.

A possible consideration is the extensive travel time—some days pack in quite a bit of sightseeing, which might be tiring for some. However, for those eager to see a lot in a short span, it offers incredible value.

This tour suits curious travelers who enjoy a mix of culture, history, and local flavors, and who appreciate small-group experiences that foster a more intimate, engaging atmosphere.

Good To Know

• Covers three countries in five days for a comprehensive regional overview.
• Small group size (max 15 travelers) for a more personal experience.
• Includes most meals and snacks, reducing the need for additional planning.
• Transport in air-conditioned minivans, making long travel days comfortable.
• Visits iconic sites such as Milestii Mici winery, UNESCO monasteries, and Soviet museums.
• Rich cultural insights, with guides providing live commentary.

An In-Depth Look at the Itinerary

Day 1: Arrival in Chisinau, Moldova

Starting in the Moldovan capital, the first impression is of a city on the rise, with broad boulevards, green spaces, and a mix of Soviet-era architecture and modern touches. Since this initial stop is just an airport meet-and-greet, it sets a relaxed tone for the trip. Travelers often appreciate the smooth pickup service, especially after a long journey.

Day 2: Milestii Mici Winery & Chisinau Highlights

The day kicks off with a visit to Milestii Mici, the Guinness World Record holder as the largest underground wine collection. The 30-minute drive from Chisinau culminates in a tour of 250 kilometers of subterranean galleries, which house over 1.5 million bottles of wine. It’s a stunning feat of storage and a chance to taste some of Moldova’s finest wines. The guide typically shares insights into the country’s wine traditions and the unique underground climate that preserves these bottles.

Following this, a four-hour exploration of Chisinau’s city center reveals a city often called “Small Rome.” The wide avenues, parks, and historic buildings along Stefan cel Mare boulevard give a sense of Moldova’s recent history and architectural style. Visitors get to see landmarks like the public parks, churches, museums, the city’s parliament, and military memorials. Travelers have noted that the city has an inviting atmosphere, with a specific charm that’s easy to appreciate on a leisurely walk.

Day 3: Cross into Romania – Iasi

Traveling north, the group moves into Romania, arriving in Iasi, one of the country’s cultural hubs. Known as the oldest university city with a vibrant arts scene, Iasi impresses with its historical buildings and botanical gardens. It’s a city that has seen centuries of history, from its early settlement to serving as Romania’s capital during WWI.

While you might expect a quick stop, the nine-hour day allows ample time to absorb the city’s atmosphere and history. Reviewers mention that Iasi’s mix of old and new, along with its academic vibe, offers a compelling contrast to Moldova’s quieter charm.

Day 4: Old Orhei and Folk Experience

Back in Moldova, the focus shifts to Old Orhei, a site that combines natural beauty and history in a way that’s difficult to match. The Cave Monastery Complex carved into limestone cliffs has been a place of spiritual retreat for centuries, with monks expanding and maintaining it over the years.

The site is a photographer’s dream, with stunning views of cliffs and the river below. The guided tour provides fascinating insights into the monastery’s history and the Christian traditions that have persisted there. Afterward, a traditional Moldovan lunch at a local family pension includes folk performances, giving a taste of authentic local hospitality and culture.

Day 5: Soviet Museum & Kvint Brandy Distillery in Tiraspol

The final day takes us to Tiraspol, the capital of Transnistria, a breakaway territory often described as a Soviet time capsule. The highlight is a guided tour of Kvint, a distillery established in 1897, known for its high-quality brandy that follows French traditions.

The tasting rooms offer a chance to sample aged spirits ranging from three to fifty years, often prompting reviewers to remark on their smoothness and complex flavors. Though some might be surprised by the Soviet-era museum and the political context, this stop provides an authentic glimpse into the region’s complex history.

What Makes This Tour Stand Out?

Value for Money: At nearly $1,000, the price covers transport, most meals, entrance fees, and guided commentary. Given the breadth of sites visited across three countries, this is quite competitive. Reviewers often mention that the cost is justified by the quality and scope of the experiences.

Comprehensive Insights: The guides provide live narration, adding context to each site—whether explaining Moldova’s wine culture, Romania’s historical significance, or Transnistria’s political status. This turns sightseeing into a learning opportunity.

Transport and Logistics: Traveling in air-conditioned minivans ensures comfort on long driving days, which are inevitable given the trip’s scope. The small group size means more personalized service, and the included hotel pickup alleviates logistical stress.

Authentic Experiences: From tasting Moldovan wines underground to folk performances in a local village, the tour emphasizes genuine, off-the-beaten-path moments that make the trip memorable.

Challenges and Considerations

While the tour packs in a lot of sightseeing, it also involves substantial travel time—most days involve several hours on the road. Some travelers might find this tiring, especially if they prefer more relaxed itineraries.

The compact schedule means limited free time at each stop, so it’s essential to stay engaged and keep up with the group. Also, the political situation in Transnistria can be confusing; some reviews highlight that it’s not recognized as a country, which might matter to certain travelers.

Who Would Love This Tour?

This trip is best suited for travelers who are curious about regional history, culture, and wine, and don’t mind a busy schedule. It’s ideal for those who appreciate small-group settings, want an all-inclusive experience, and are eager to see a diverse array of sites in a short time frame. History buffs, food and wine enthusiasts, and adventurous spirits will find plenty to enjoy here.

The Sum Up

This five-day tour offers a compelling way to explore Moldova, Romania, and Transnistria without the stress of planning each detail. It combines immersive cultural visits with the comfort of guided transport and meals included, making it a practical choice for curious travelers keen to maximize their limited time.

While it’s a full schedule, the variety of sites—from underground wineries to historic monasteries and Soviet museums—ensures each day feels fresh and engaging. The small group size fosters a more intimate experience, and the inclusion of local tastings and folk performances adds memorable flavor.

For those seeking an authentic, cost-effective way to see a lesser-known corner of Europe packed with history, culture, and surprises, this tour checks all the boxes.

FAQs

Is hotel pickup included in the tour?
Yes, the tour offers hotel pickup and drop-off in air-conditioned minivans, making it easy to start your adventure without extra logistics.

How many people are in the group?
The tour is limited to a maximum of 15 travelers, ensuring a small, more personal experience.

What meals are included?
Most meals, snacks, coffee, and tea are included, with a buffet lunch and dinner provided during the trip.

Do I need to bring my passport?
Yes, travelers must provide their passport details at booking, as you’ll cross borders between Moldova and Romania, and visit Transnistria, which requires valid identification.

Is the tour suitable for all fitness levels?
The tour requires a moderate physical fitness level, given the amount of walking and sightseeing involved, but it’s generally accessible for most travelers.

Can I cancel the tour if my plans change?
Yes, free cancellation is available up to 24 hours before the start, offering flexibility to adapt your plans.

This tour offers a well-rounded, engaging introduction to three fascinating regions, making it a solid choice for travelers eager to see a lot with minimal hassle.