1. Get the scent of romance at Viru Gate
City-centre settings simply don’t get any more romantic than the twin fairy-tale turrets of the Viru Gate. Constructed as part of Tallinn’s medieval defences back in the 14th century, the gate nowadays marks the entrance to the Old Town. Look out for the colourful permanent flower market a short stroll along from the gates in the direction of Viru roundabout, the perfect location to linger awhile and smell the roses with that special someone.
Viru tänav, Old Town
2. Have a sneak peek at the KGB Museum
The 22-storey Hotel Viru was built during the Soviet era for foreign travellers visiting the city. What guests weren’t told about was the secret listening rooms on the unlisted – indeed, flatly denied – 23rd floor. When the Soviets fled in the 1990s, Estonians were shocked to discover the extent to which the KGB had bugged every room, the tables in the restaurants, even the ashtrays at the bar. Nowadays you can book a tour of the listening room, complete with its racks of Soviet-era electronics, tape machines, uniforms, telephones, gas masks, and other Cold-War paraphernalia.
4 Viru väljak, Südalinn
+372 680 9300
3. Set sail for adventure at the Estonian Maritime Museum
Situated on the Baltic coast, Tallinn boasts a rich and fascinating seafaring heritage. See it for yourself at the Estonian Maritime Museum. Straddling two eye-catching venues – a 500-year-old cannon tower affectionately named Fat Margaret, and a gigantic Second World War Seaplane Hanger, one of the oldest reinforced concrete shell structures on earth – you can mooch around everything from real medieval shipwrecks to Lembit, a one-of-a-kind pre-war submarine and a longstanding mascot of the Estonian navy. Talk about an immersive day out.
6 Vesilennuki, Kalamaja
+372 6200 545
4. Savour the views from the Kohtuotsa platform
For a genuinely unmissable photo op, schlep up the eastern corner of Toompea Hill and look out for some understated typographic street art (bearing the Insta-friendly legend ’The Times We Had’) on the edge of a broad viewing platform. The magical medieval rooftops of Tallinn are obligingly splayed out before the Kohtuotsa viewing platform. The Soviet-era TV tower in the background offers a cool space-age backdrop to your FOMO-inducing holiday snaps. In summer it’s a lovely spot to linger for a coffee and watch the street performers.
12 Kohtu, Toompea
5. Meet the cool kids at Kalamaja district
Once upon a time a humble fishing enclave – the name literally translates as ‘fish house’ – the now flourishing district of Kalamaja is the heart of Tallinn’s groovy tech-led renaissance. Its simple wooden homes have been colonised by digital entrepreneurs and its buzzing cafes and bars – most notably clustered in the Telliskivi Creative City complex – are awash with bright young things making stuff on laptops. Dinner at F-hoone (60a Telliskivi) and a night out at Sveta Baar (62 Telliskivi) will convince you, if you still need it, why Kalamaja is suddenly such a catch.
6. Have a holy moment at Alexander Nevsky Cathedral
Whatever your faith, or otherwise, you’ve got to admit this Russian Orthodox pile atop Toompea Hill is an exquisite gem of a building. Built in 1900 by the Russians who ruled the roost here back then, it’s a glorious confection of chic black onion domes and vividly realised porticos and cornicing. The striking upper portion holds no fewer than 11 bells, including Estonia’s biggest, and the church interior is studded with detailed mosaics and richly-jewelled icons. It doesn’t get much more divine than this.
10 Lossi plats, Vanalinn
+372 644 3484
7. Baroque out at the Kadriorg
If you’re looking for a sublime slice of grandeur and old-school romance, make your way to the baroque splendour of the Kadriorg Palace, a short tram ride from downtown Tallinn. Set in dainty manicured grounds with ornate fountains, the palace itself is an eye-catching hunk of multicoloured tsarist stucco if ever there was one. Even better, inside you’ll also find the palace’s eponymous art museum, which includes the biggest and richest collections of 16th-to-20th century paintings and sculpture in the country. A charming little oasis of refinement.
37 A. Weizenbergi, Kadriorg
+372 606 6400
8. Flag down a legend at the Danish King’s Garden
Tucked in between the old city wall and Tallin’s Lower Town, this part of Toompea Hill was the mythical (well, probably) birthplace of the world’s oldest national flag. Way back in 1219, the story goes, King Valdemar of Denmark camped here on the eve of conquering Tallinn. The locals fought back, and so Valdemar prayed for his life and that of his men. From the skies descended a scrap of red cloth with a white cross, the inspiration for Denmark’s flag. The Danes went on to rule Estonia for more than a century. Today it’s a grand picnic spot, with a sculpture of three medieval monks to underline the creepy/medieval tone.
9 Lühike jalg, Vanalinn
9. Drink in the vibes at the Põhjala Brewery
It doesn’t get any more real than the Põhjala Brewery. Established by four beer-swilling pals a little over a decade ago, its oak-aged imperial stouts and sumptuous porters are a legend among locals. The attached taproom is well worth stopping by for a sup, with 24 taps and Texas BBQ-themed bar snacks overseen by chef Michael Holman. Brilliantly, there’s also an on-site site sauna. By the way, if you don’t know how to say the name, the Põhjala team say ‘it's pronounced as if someone punched you in the stomach after you said that you don't like dark beers’. Right then.
5 Peetri, Kalamaja
+372 5646 7836