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Tallinn’s glorious walled Old Town looks like something straight out of a fairytale, but the romantic skyline hides a buzzing modern city with a cutting-edge cultural vibe – you can explore a unique fusion of medieval streetscapes, baroque palaces, museums and cosy taverns on a Tallinn city break.
Estonia’s capital has one of the best-preserved medieval city centres in Europe. Most Tallinn holidays begin in the UNESCO-listed Old Town, where the winding streets are lined with creeper-hung towers, elegant church spires and old merchants’ houses. This cobblestoned labyrinth is full of surprises, from the only intact Gothic town hall in Northern Europe right up to the spectacular views across Tallinn from atop Toompea Hill.
Tucked away behind the facades of ancient buildings are the funky cocktail bars, brew houses and bistros that make weekend breaks in Tallinn so much fun. The city’s nightlife experience is legendary, so if you’re in town for a stag or hen party then you should have a ball.
While most Tallinn city breaks focus on the Old Town, it’s well worth venturing east beyond the medieval walls to explore the modern city centre. In this less visited area of Tallinn, cheap accommodation deals abound and there is still loads to do – try adding a little extra spice to your holiday by quaffing craft beer in the hipster Kalamaja neighbourhood, tracking down collectibles at the Balti Jaam train station flea market or picnicking in manicured Kadriorg Park.
Feeling adventurous? Plan a day trip away to explore the beaches north of the city centre, the historic city of Tartu or Lahemaa National Park.
The best time to visit is generally in the late spring or summer, when balmy weather makes sightseeing a pleasure and the city’s calendar throngs with fun festivals. If you’re after a cheap Tallinn break, however, then look for deals outside July and August – always the most popular months.
Winter is a magical time for a Tallinn city break, particularly over the Christmas market season. Adrenaline junkies should take the opportunity to combine some city sightseeing with a trip to cross-country skiing mecca Otepää.
Tallinn Old Town Days, usually held at the end of May, signals the start of summer in the city. A huge variety of musical, theatrical and sporting events enliven the Estonian capital’s medieval core, making this an ideal time to plan your a weekend break.
In July, the open-air Beer Summer festival showcases local and international craft beers alongside high-end musical entertainment – past acts have included Moby and the Pet Shop Boys. With a line-up of crazy amusements (bungee jumping off a crane anyone?), Beer Summer is an ideal focus for hen and stag parties.
Visit between the end of November and early January to enjoy the atmospheric Christmas market that takes over the city’s Town Hall Square every year. With snow-covered stalls, Santa’s grotto and a famous Christmas tree, it’s guaranteed to get you in a festive mood.
2 hrs 50 mins
(from London)
Euro (€)
Estonian
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5 min read
Updated 19 October 2023