Estonia in 2-3 days

Day one

Spend your first day firmly entrenched in the cobblestone streets of Tallinn’s old town. Explore the alleyways, duck into souvenir shops and get to know this quaint former Soviet stronghold that is packed with authentic guild houses, towering church spires and fortress battlements. Sit down to lunch at one of the cafes or restaurants on Town Hall Square — once executions were held here but now the sprawling cobblestone square is lined with lively cafes and the only complete
gothic town hall in Northern Europe. After dark, order a pint or a shot of Vanna Tallinn (the local spirit) in one of the many old town bars after dark.

Day two

Tuck into a hearty Estonia breakfast of bread, meat and cheese before exploring some of Tallinn’s museums. The Museum of Medieval Torture Instruments is not for the squeamish, while the Museum of Occupations is a poignant reminder of Soviet rule, when many farms and properties were seized by the state, Estonian songs were banned and dissidents were executed or sent to work camps in Siberia.

Afterwards, tick off any sights you haven’t yet seen in the old town. The lovely neoclassical Russian Orthodox Church will make you think you’ve stepped into Moscow’s Red Square, while Kiek in de Kok
is a 15th century defence tower on the slopes of Toompea hill — the name means ‘peep into the kitchen’, because soldiers on duty used to look down the chimney and into the kitchens of surrounding homes.

Day three

While the old town is Tallinn’s main attraction, the modern city centre adjacent is also worth a stroll, with steel and glass shopping centres, swanky clubs for a big night out (try Vertigo and meet the city’s celebs) and 21st century architecture.

In 7-9 days

Days 1-3

Stick to the itinerary above.

Days 4-5

Get to know Tallinn in even more depth, visiting Fat Margaret’s Tower, a cannon tower which historically defended the seaward side of the old town and today houses the Estonian Maritime Museum, and stopping in at Kadriorg Palace, a grand baroque palace built by Peter the Great which sits in the middle of a leafy park that also houses the new Kumu Art Museum, a treasure trove of traditional Estonian and Russian art.

Days 6-9

It’s time to get out of Tallinn and explore a little more of Estonia. Take the train down to the cultural capital of Tartu and spend a night exploring this charming university town, a world away from what will feel like the hustle and bustle of Tallinn.

Finally, head for the islands of Saaremaa or Hiiumaa in the Baltic Sea, famous for their pristine nature, beaches and spa retreats, before returning to Tallinn for your flight, train or ferry onwards.