Tallinn

One of the best-preserved medieval old towns in Europe and a total fairy tale — Tallinn's Vanalinn, a car-free maze of cobbled lanes, gabled merchant houses, Gothic spires, hidden courtyards and turreted stone walls, largely unchanged since its Hanseatic heyday. Simply wandering its storybook streets, discovering a medieval church, a cosy cellar tavern or a viewpoint around each corner, is the essential Tallinn experience — pure enchantment, especially early morning or under snow. Give it a whole day of aimless, joyful exploring. Utterly magical and unmissable. The heart of the city.

The beating heart of the old town — Raekoja plats, a beautiful cobbled square ringed by pastel merchant houses and dominated by the striking Gothic Town Hall, the oldest in northern Europe, topped by 'Old Thomas', the city's guardian weathervane. Once a bustling medieval market, it's still the city's gathering place, lined with café terraces in summer and transformed into a magical Christmas market in winter. Soak up the atmosphere over a coffee or mulled wine, and admire the Town Hall; it's the postcard heart of Tallinn. A lovely, central and essential highlight. Charming year-round.

The upper town crowning the old town — Toompea Hill, the ancient seat of power, home to the pink baroque Toompea Castle (now parliament), the spectacular onion-domed Alexander Nevsky Cathedral, the medieval Dome Church, and above all the famous viewing platforms (Kohtuotsa and Patkuli) with breathtaking panoramas over the red-tiled roofs, spires and city walls to the sea beyond. Climb the cobbled ramp to the top for the iconic Tallinn view, especially glorious at sunset. A magnificent, essential highlight and the best vista in the city. Simply stunning; go for the views.

Tallinn is ringed by remarkably intact medieval fortifications — nearly two kilometres of stone walls studded with dozens of red-roofed defensive towers, among the best-preserved in Europe. Walk a section of the ramparts (accessible via the Hellemann Tower or the Nunne-Sauna-Kuldjala towers), climb the atmospheric Fat Margaret and Kiek in de Kök tower-museums, and admire the fairy-tale scene of turrets and red roofs, especially from the famous Viru Gate. A wonderful, evocative plunge into the city's medieval past. A must-see; the walls and towers make Tallinn a storybook. Atmospheric and photogenic.

The hip, beating heart of modern Tallinn — Telliskivi Creative City, a former industrial complex in the Kalamaja district transformed into the city's coolest cultural hub, full of design shops, galleries, hip restaurants, craft-beer bars, street art, markets and the superb Fotografiska photography museum. Wander the buzzing, mural-covered grounds, browse the design stores, and eat and drink among the creative crowd; it's a brilliant window into cool, contemporary Estonia, a total contrast to the medieval old town. A vibrant, essential highlight. Cool, creative and lots of fun.

One of the best museums in the Baltics — the Seaplane Harbour (Lennusadam), a maritime museum housed in a vast, cathedral-like former seaplane hangar, where you can climb aboard a real WWII-era submarine, explore historic ships and seaplanes, and enjoy hands-on interactive exhibits. Superbly done, immersive and great for all ages, it tells the story of Estonia's seafaring history in a spectacular space, right on the harbour. A wonderful, engaging highlight, especially with kids or on a rainy day. Excellent and unexpected; a real crowd-pleaser. Don't miss the submarine.

A slice of imperial elegance — Kadriorg, a beautiful pink baroque palace built by Tsar Peter the Great for his wife Catherine, set in gorgeous landscaped gardens with ponds, fountains and flowerbeds, now housing a fine collection of foreign art. Stroll the lovely park (a favourite of locals), admire the palace and its formal gardens, and visit the nearby presidential palace and the excellent KUMU art museum. A graceful, tranquil escape from the city, especially lovely in spring bloom or autumn colour. A charming, cultured highlight in the leafy east. Beautiful and peaceful.

Estonian food is hearty and increasingly hip — from rustic medieval-tavern fare (the famous Olde Hansa serves it by candlelight in period costume) of hearty stews, game, black bread and spiced ale, to a superb, creative 'new Nordic' scene using foraged, local ingredients that has earned Tallinn Michelin stars. Feast in a candlelit medieval cellar for atmosphere, or book a modern Estonian restaurant for the cutting-edge cuisine; both are delicious and great value. A tasty, characterful highlight that spans centuries. Come hungry; the range is a delight.

The most spectacular church in the city — the Alexander Nevsky Cathedral atop Toompea Hill, a magnificent Russian Orthodox cathedral of soaring onion domes, built during the tsarist era, its ornate interior glittering with icons, mosaics and gilded decoration. A striking, exotic contrast to the Gothic Lutheran churches of the old town, it dominates the upper-town skyline and faces the parliament across the square. Step inside to admire the opulent, incense-scented interior (dress modestly), and photograph the famous domes. A beautiful, unmissable landmark on Toompea. Grand and photogenic.

The best market in the city — Balti Jaam Turg, a wonderfully revamped market hall beside the train station on the edge of the old town and Kalamaja, spread over several floors selling fresh produce, meats, cheeses, street food from around the world, vintage clothes, antiques and crafts. Graze the food stalls, browse the eclectic vintage and antique sections, and soak up the buzzing local atmosphere; it's a delicious, characterful window into everyday Tallinn life. A tasty, colourful highlight away from the tourist trail. A local favourite; great for food and finds.

Estonia's flagship art museum — KUMU, an award-winning modern building on the edge of Kadriorg Park, housing a superb collection of Estonian art from the 18th century to the present, including striking works from the Soviet era and cutting-edge contemporary art. Beautifully designed and thoughtfully presented, it offers a fascinating window into Estonia's history, identity and creativity through its art, particularly the powerful Soviet-period and post-independence works. A rewarding cultural highlight in a lovely park setting. Excellent for art lovers; illuminating and world-class. A cultured half-day.

A showcase of cool, contemporary Tallinn — the Rotermann Quarter, a regenerated area of old brick warehouses and factories between the old town and the port, imaginatively transformed with bold modern architecture into a stylish district of design shops, restaurants, cafés and offices. Wander the striking streets where 19th-century industrial buildings meet daring contemporary design, browse the boutiques, and grab a bite; it's a great example of the city's forward-looking, design-savvy side. A pleasant, stylish stroll bridging medieval and modern Tallinn. Sleek and interesting.

Tallinn has its own seaside — Pirita, a long, sandy Baltic beach north-east of the centre, popular with locals in summer for swimming, sunbathing and watersports, beside the atmospheric ruins of a medieval convent and a marina. Stroll the seaside promenade from Kadriorg, relax on the sand, and enjoy the fresh sea air and views back to the city and old town across the bay. Not the Caribbean, but a lovely, breezy escape in the warm months. A pleasant, relaxed seaside highlight in summer. Best on a sunny day; refreshing and local.

One of the old town's great fortification towers — Kiek in de Kök, a mighty 15th-century artillery tower (its name means 'peep into the kitchen', for the view it gave over the town) now a fascinating museum of the city's defences, connected to the atmospheric Bastion Tunnels dug beneath the walls. Explore the tower's exhibits on medieval warfare and climb for views, then take the guided tour through the eerie underground passages that have sheltered soldiers and citizens over the centuries. A fascinating, atmospheric plunge into the city's fortified past. Great for history lovers; the tunnels are a highlight.

Tallinn's nightlife punches well above its size — from cosy medieval cellar bars and cool craft-beer and cocktail spots in the old town, to the hip bars, clubs and live-music venues of trendy Telliskivi and Kalamaja, all cheaper than the Nordic capitals across the sea. Sip a spiced medieval ale by candlelight, hunt out a hidden speakeasy, or party with the young creative crowd in Telliskivi; the scene is lively, affordable and fun. A brilliant way to round off a day in the city. Energetic and great value; something for every mood. A fun night out.