Eastern European holidays to inspire your next trip

The capital of Bulgaria is perfect city break material thanks to the way it blends the historic with the contemporary, with a thriving street art scene juxtaposed with layer upon layer of history.

You’ll see the evidence of Sofia’s patchwork, and endlessly fascinating, past, for yourself as you wander its streets. Soak it up, this is what holidays in Eastern Europe are all about.

Set yourself up for the day with brunch and coffee at one of the city’s countless appealing cafés,  then take in the Alexander Nevsky Cathedral, the Boyana Church, a UNESCO World Heritage Site, and don’t miss the picture-perfect sunset views at the Ivan Vazov Theatre.

And if you’ve got time for more than just a city break and are keen to see more underrated destinations in Eastern Europe, when you’re done exploring Sofia, make for the ski fields of Bankso in winter, or set a course for one of the relaxing resorts in Sunny Beach , where the locals head for a bit of R&R on the Black Sea, for a classic beach holiday with a Bulgarian twist.

Bulgaria might not be the first place that springs to mind when you start thinking about where your next fix of vitamin sea will come from, but Sunny Beach is one of the best Eastern European beaches there is, with 7km of golden sand, and it 100% lives up to its name.

It’s nigh-on impossible not to fall in love with Prague. This is one of the best cities in Eastern Europe for a short but incredibly sweet break that offers something for absolutely everyone.

Roaming its cobbled streets or squeezing into a cosy café, you wouldn’t be blamed for thinking you’ve strayed onto a film set. You have, in fact, strayed onto a UNESCO World Heritage Site, and you’ll see why it's been given that title.

This is one of those cities to visit in Eastern Europe that rewards the wanderer, especially the wanderer who explores the streets of Staré Mesto (Old Town), Malá Strana (Little Town) and Hradcany.

The stars of the show are the famous Charles Bridge, the Old Town Square with its fascinating astronomical clock, and, of course, the castle. But once you’ve seen those three, keep exploring, browsing Prague’s museums and pacing its streets.

And when sore feet need a break, you could always take to the water, with a boat trip on the Vltava River.

Everyone who comes back from a city break in Warsaw knows for a fact that they’ve discovered one of the best destinations in Eastern Europe. Explore its Christmas markets, or visit between May and September, which is when the city really comes to life.

As anyone who’s enjoyed holidays in Eastern Europe will tell you, the best way to discover these cities is on foot, so bring a comfy, trusty pair of shoes, and hit the streets.

After you’ve explored the Old Town and the Neon Museum, towards the end of the day, take a stroll along the riverside, treating yourself to a drink at one of the countless riverside cafes.

And don’t forget, the perfect places to fuel up for all those steps aren’t the tourist traps in the Old Town, they’re traditional milk bars (bar mleczny). This is where you’ll want to try Polish classics. Spoiler, there’s much more to Polish cuisine than just pierogies.

Set on the legendary river Danube, which laps the riverbanks of so many of the most beautiful cities in Eastern Europe, there’s so much to do in Budapest that you could stretch out a city break here into far more than a long weekend.

First on your list is probably one of the city’s legendary spas, and no wonder. Budapest was built over a network of hot springs said to have a whole host of curative properties. Head for the famous Széchenyi baths, or try a different spot for a slightly quieter experience.

Dry off, then go for a tram or a boat ride, treat yourself to a coffee at one of its impressively classic coffeehouses, explore the castle, the City Park, the Basilica of St Stephen… the list goes on. Round off a long day of sightseeing with a drink at one of many rooftop bars with magical views.

If you’ve got a little more time on your hands and have one week in Eastern Europe to fill, remember Budapest and Prague are easy to travel between by train, so you could see two of the most famous cities in this neck of the woods on one trip.

There’s so much to see in Slovenia, the ideal destination for extended holidays in Eastern Europe, but even if you’ve only got time for a short city break, the capital, Ljubljana, ticks all the right boxes.

Like the other atmospheric cities on this list, the run-up to Christmas is a magical time to visit Ljubljana , but spring and even summer are the best times to visit to see the city at its best.

This medieval town, with countless whitewashed buildings topped with terracotta tiles, is the perfect destination for art lovers, who’ll adore the Museum of Modern Art, the National Gallery of Slovenia and the street art scene. Architecture lovers won’t be disappointed either.

Stroll the streets and parks, sample local food and, most importantly, the local wine (largely unknown, but totally delicious), and revel in one of the best Eastern European city breaks there is.

You can’t get any further east in Europe than the fascinating country of Georgia, perched on the other side of the Black Sea. The capital, Tbilisi, will win you over in seconds, with its quaint, colourful old town and the Persian, Russian and Ottoman influences that shaped it shining through.

And although this list has been all about the best city breaks in Eastern Europe, it’d be a shame to visit Georgia and not take the chance to see more of what this intriguing destination on the border with Asia has to offer, from cave cities to stunning historic churches, and national parks to vineyards. 

With Tbilisi as your base, you’re ideally placed to explore as far afield as you like, discovering places unspoilt by mass tourism that you’ll remember forever.