Moldova & Ukraine holidays

Moldova and Ukraine lie at the very edge of Europe. These frontier countries sit sandwiched between Russia and the West, and have been pushed and pulled in an East-West game of tug-of-war in recent history.
Some regions are attached to their Soviet past and actively loyal to modern day Russia, but you only need to hop across a border or board a train to find yourself in a westwards looking city that looks and feels European, full of baroque architecture and café culture.
Moldova’s capital Chisinau feels strongly Soviet, having been rebuilt in brutalist style after a massive earthquake and World War II laid waste to it. Yet venture into the surrounding countryside and you’ll find ancient monasteries and vast wine cellars, that speak of the country’s long and varied history. Across the border, western Ukraine is more European in feel. Beautiful Lviv, Ukraine’s cultural hub is home to a UNESCO-listed Old Town that could rival Vilnius or Krakow for gorgeous good looks. Meanwhile, mighty Kyiv, the capital, is slowly emerging as a modern European hotbed of culture and nightlife.
A tour of both Moldova and Ukraine will also hop into the self-declared independent microstate of Transnistria, a fascinating oddity lying on the border of both countries. Transnistria is staunchly pro-Russian and very attached to its Soviet past, with busts of Lenin peppered around its capital, Tiraspol.
Visiting these countries on a single trip is a chance to gain an overview of this little visited corner of Europe. In fact, you’ll be blazing a trail; with just over 120,000 visitors a year, Moldova is one of the least visited countries in the world. It also makes good practical sense. Although Moldova has a good selection of standout highlights, distances between them are short and you can fit them into two or three days. Equally, visiting Ukraine alone would be to miss out on its tiny western neighbour – not least the wonderful wine produced there. So, it really does make sense to combine the two countries. Cheers!

Highlights of Moldova & Ukraine

Weeklong trips to Moldova and Ukraine tend to focus on the key cities and nearby attractions. That’s typically Chisinau in Moldova (plus the 14th century Orhei Monastery and the Cricova wine cellars), and Odessa, Lviv and Kyiv in Ukraine. They always include Transnistria, too, because it’s just so fascinating, and some tours include the option to visit Chernobyl. Two-week tours may include a walk in the Carpathian Mountains outside Lviv, and the beautiful city of Chernivtsi, in the foothills, which is home to elegant theatres and churches and feels quite different to the rest of Ukraine. In Moldova, you may visit the Republic of Gagauzia, a small strip of land which once vied for independence from Moldova alongside Transnistria, but parked its aspirations when it was granted special legal status in 1994. Some Moldova and Ukraine holidays take in Belarus or Romania, too.

Chernobyl, Ukraine

A guided exploration of Chernobyl and the abandoned town of Pripyat is a fascinating, if unsettling experience. The Chernobyl power plant lies 130km north of Kyiv and in April 1986 one of its reactors exploded, spreading lethal radiation, first over Pripyat and later right across Europe. Specialist tours that meet strict safety standards take you right into the exclusion zone, where today radiation levels are similar to that of a standard X-ray. The band Suede used footage of Pripyat in their music video for Life Is Golden – it’s a great taster of this tragically frozen in time place.

Chisinau, Moldova

Pronounced Kishi-Now, Moldova’s capital is one of Europe’s greenest cities and, happily, all those trees offset the grim effect of the brutalist architecture found everywhere. Just outside of the capital lie the vast wine cellars of Cricova, 80 metres underground, and interlaced with tunnels that have their own street names and stretch for more than 120km.


Over 2.5 million people live in Ukraine's mighty capital, Kyiv. It’s seen its share of uprisings and oustings, but today it’s also a cultural place, with a lively café and nightlife culture. There are plenty of golden domed cathedrals and monasteries, too, creating an unforgettable cityscape.


Lviv is the cultural heartland of Ukraine, bristling with baroque architecture, but also boasts a cosmopolitan mix of Polish, Jewish, Hungarian and Armenian history. The cobblestone streets of its Old Town are really beautiful, and you can climb the clock tower for panoramic views over them.


Ukraine’s third largest city, Odessa sits on the Black Sea coast. Catherine the Great founded it at the end of the 18th century, as a well-designed bolthole by the sea, full of baroque and renaissance buildings, and she invited immigrants from all over Europe to settle here. Odessa became a multicultural place, home to Jews, Turks, Armenians, Italians, Germans and Poles. This diversity proved its downfall come WWII, with a massacre of Jews here in 1941 and 1942. Today, Odessa’s tree lined streets and sandy beaches are popular again and many of its great buildings, left to decline during Soviet times, are being restored.


This is one of Europe’s strangest destinations. It’s a self-declared republic occupying a narrow strip of land in the east of Moldova, which declared independence after the Soviet Union broke into pieces in 1991. This microstate is officially only recognised by the people who live there and other unrecognised breakaway Soviet states – a fairly niche crowd – but it has its own currency, postal service and border force. Transnistria clings fiercely to the former Soviet days and is staunchly pro-Russian, although it gets little financial support in return. There are busts of Lenin all over its capital city, Tiraspol. Nearby, the town of Tighina was once an important trading centre and has an impressive 16th century fortress standing on the right bank of the Dniester River.

Our top Ukraine Holiday

Eastern Europe small group tour

Eastern Europe small group tour

Explore the best of Eastern Europe's least visited regions

From £3475 22 days ex flights
Small group travel:
Travel Team
If you'd like to chat about Ukraine or need help finding a holiday to suit you we're very happy to help.


Organised tours to Moldova and Ukraine are typically run as small group trips, with no more than 16 people and a tour leader. There will also be local guides at certain places. Transport is by private bus and train, with some tours using the sleeper train between Odessa and Lviv. Distances between key sights in Ukraine are often long, so expect some fairly chunky journeys. The train between Lviv and Kyiv, for instance, takes eight hours. Crossing the border between the two countries can also take a little while – pack some patience with your passport.

Travelling in Moldova and Ukraine is all about soaking up cultural sights and not hiking up trails or lazing on beaches. There are often guided city tours in the morning with free time to explore under your own steam in the afternoon and the pace is busy enough to give a good overview of the two countries without feeling like you’re on a whistle-stop tour.
Written by Joanna Simmons
Photo credits: [Page banner: Michal Huniewicz] [Top box (Transnistria): Clay Gilliland] [Chernobyl: Jorge Franganillo] [Odessa: Oleksii Leonov]