Europe's Frontier: Moldova & Ukraine

Fly to Chisinau, transfer to hotel. Stay: Klassik Hotel or similar.

This morning we set out on foot from our hotel for a walking tour of the Moldovan capital. Although the city dates back to 1420, a huge earthquake in 1940 destroyed most of the historic centre, while WWII finished the job off. Chisinau was then rebuilt in a Soviet-style, leaving a city dominated by Brutalist buildings, but there are some real quirky gems including the now abandoned Winter Circus, Triumphal Arch and the bell tower of the Nativity Cathedral. The central market is another highlight, first opened in 1825 it has been the centre of life in the city ever since. It's worth braving the crowds for lovely fresh fruit, nuts and wine. Heading out of the city we stop for a traditional home-cooked lunch in a small farmstead. From here we visit the beautiful, isolated hilltop Orhei Monastery dating back to the 14th century. Our final stop before returning to Chisinau is the Milestii Mici Winery, home to the largest wine cellar in the world! Here we will drive down into the cellar in the tour bus, past hundreds of barrels of the ‘holy drink' as it's known locally. We will try several varieties of wine and learn about the fascinating history of oenology in this unknown corner of Europe. Stay: Klassik Hotel or similar.

Our destination for today is one of Eastern Europe's strangest. Transnistria is a self-declared republic occupying a narrow strip of land in the east of Moldova. A microstate, officially only recognised by the people who live there, no one else! Yet they have their own currency, postal service and border force. The region harks back to the days of the USSR and is staunchly pro-Russian, although it gets little financial support in return. There are photo-worthy busts of Lenin all over the city. No trip to Moldova is complete without seeing Transnistria. In the late afternoon we transfer to Odessa on Ukraine's Black Sea Coast. Journey time is about 2 hours, however, the border crossing between Moldova and Ukraine may take some time. Stay: Hotel Alexandrovsky or similar.

This morning we wake up in Odessa, Ukraine's third largest city, on the Black Sea coast. A warm water port, Odessa has had a short but turbulent history. When founded in the 18th century Russia's Catherine the Great invited immigrants from across Europe to come and make their fortune in Odessa, thus creating a thriving multicultural city of Jews, Turks, Armenians, Italians, Germans and Poles, with the outbreak of WWII this population diversity would sadly be its downfall. In more recent times the city has had its problems especially during the 2014 revolution, but now the city is booming once again. Its beautiful tree-lined avenues and seaside boulevards are a perfect place to relax and see a different side to Ukraine. The ornate opera house and Potemkin Steps are architectural must-sees. After a city tour, we enjoy free time, before boarding the overnight sleeper train to Lviv. Stay: Sleeper train.

We arrive early into Ukraine's cultural capital Lviv, stopping for breakfast at our hotel and storing our luggage, we will try and obtain a couple of day rooms so you can freshen up, but please note this is not always possible. We then head out for a morning walking tour of this beautiful city, before enjoying free time in the afternoon. We recommend climbing the clock tower of the town hall for a panoramic view of the old town. Lviv's UNESCO listed old town easily competes with the likes of Krakow and Vilnius in the charm and history stakes! It's full of colourful townhouses, fine churches, cobbled streets and cosy cafes. Ukrainian cultural identity is stronger here than anywhere else in the country, but with a wonderful mix of Polish, Jewish, Hungarian and even Armenian history thrown into the mix. Lviv really is a delight and surprisingly untouched by mass tourism. Stay: Modern Art Hotel or similar.

This morning we board the train to Kyiv (journey time 8hrs approx.), Ukraine's mighty capital city and home to over 2.5 million people. The Ukrainian capital seems to have hardly left the news in recent years, sadly for all the wrong reasons, but its citizens are made of strong stuff and are keen to show their beautiful city to the world. There will be some free time in the evening to enjoy the city or take dinner on the capitals most famous street, Khreshchatyk. Stay: Ukraine Hotel or similar.

This morning we enjoy a walking tour of Kyiv's main sights, including Maiden Square, the site of the revolutions of 2004 and 2013. As well as St. Sofia Cathedral and the Monastery of St. Michael Archangel. The afternoon is free for you to enjoy this fascinating city at your leisure. You may choose to visit the Pechersk Lavra Monastery with its complex of caves housing mummified nuns. While the National Museum of the History of Ukraine in the Second World War gives you a macabre, Soviet perspective, it also offers great views of the city. Stay: Ukraine Hotel or similar.

Our tour ends after breakfast.