Day 1 — Arrival & the Lower Town
Settle in and walk straight to Town Hall Square (Raekoja Plats), the medieval heart of the city. The Gothic Town Hall and its octagonal tower anchor a square ringed by 15th-century merchant houses. Climb the tower for your first orientation over the rooftops.
Wander the Lower Town's lanes at a slow pace — Katariina käik (St Catherine's Passage), a narrow medieval alley lined with glassblowers, ceramicists, and textile workshops, is one of the most charming corners of the city. Dinner in one of the old town's cellar restaurants, many set in genuine medieval merchant vaults. First evening is for orientation — walk the walls, find the towers, get your bearings.
Day 2 — Toompea Hill & the Upper Town
A full day on Toompea. Climb via Pikk jalg (Long Leg) in the morning and take your time — this hilltop has been the seat of power through every occupying force in Estonian history, Danish, German, Swedish, and Russian. The Alexander Nevsky Cathedral, an onion-domed Orthodox cathedral built in 1900 as a deliberate statement of Russian imperial dominance, sits strikingly against the Gothic streets around it. Toompea Castle next door now houses the Estonian parliament, the Riigikogu.
Visit both viewing platforms — Kohtuotsa and Patkuli — for the full panorama over the Lower Town's red roofs, church spires, and the Baltic Sea beyond. Spend the afternoon in Toompea's quieter residential streets, then descend via Lühike jalg (Short Leg) into the Lower Town for the evening. Climb St Olaf's Church tower if you have energy left — 258 steps for a view that was, briefly in the 16th century, the highest vantage point on earth.
Day 3 — Kalamaja & Telliskivi Creative City
Leave the old town for Kalamaja, Tallinn's wooden-house district and creative core. Breakfast at the Balti Jaama Turg (Baltic Station Market) — smoked Baltic sprat, herring, and dense rye black bread from local vendors.
Spend the day at Telliskivi Creative City, a former industrial complex of brick factory buildings now packed with design studios, vintage shops, independent cafés, and music venues. On weekends the flea market is one of the best in the Baltics. Walk the neighbourhood's wooden streets in the afternoon — Kalamaja was working-class and semi-derelict two decades ago; it's now Tallinn's most sought-after address, and the contrast in architecture (grand wooden villas next to modest workers' cottages) tells that story clearly.
Evening: Põhjala Brewery's taproom for Tallinn's best craft beer, or Pudel for a quieter neighbourhood bar experience.
Day 4 — Noblessner & the Seaplane Harbour
Walk north from Kalamaja into Noblessner, the former submarine factory district on the waterfront, rapidly developing into a design and dining quarter with a marina promenade. The Seaplane Harbour (Lennusadam) is the anchor attraction — Estonia's maritime museum, set inside a restored Art Nouveau seaplane hangar. The 1936 submarine Lembit is the centrepiece and fully explorable; historic seaplanes, icebreakers, and a minelayer fill the rest of the hangar. Budget at least two hours.
Afternoon: walk back along the coast towards the old town, or take a slower route through Kalamaja's side streets. Evening: dinner somewhere in the old town serving contemporary Estonian food — Leib Resto or Rataskaevu 16 both do strong versions of elk stew and smoked fish.
Day 5 — Kadriorg Park, KUMU & Pirita
A slower day east of the centre. Kadriorg, the baroque palace and park complex built by Peter the Great for Catherine I, opens the day. KUMU, at the park's entrance, is the finest art museum in the Baltic states — a genuinely strong collection of Estonian art from the 18th century through the Soviet period to today. Kadriorg Palace itself is smaller but worth a shorter visit for its foreign art collection.
Walk the park's formal gardens and ponds, then continue on foot towards Pirita, about thirty minutes further — a marina, a long sandy beach, and the ruins of the 15th-century Pirita Convent along the way. In summer this is where Tallinn residents spend their weekends; it's a genuinely different side of the city from the medieval core.
Evening: back to the centre for dinner, or stay in Pirita if the weather holds.
Day 6 — Lahemaa National Park Day Trip
Lahemaa is Estonia's largest national park, roughly 70km east of Tallinn — coastal cliffs, boulder fields, dense boreal forest, fishing villages, and restored manor houses largely untouched since the Soviet era. It's best done by hire car or an organised day tour, since public transport connections between the park's scattered sights are limited.
The Viru bog trail — a wooden boardwalk across a raised peat bog with a small observation tower — is the park's signature walk, meditative and otherworldly, manageable in under two hours. Pair it with a visit to Palmse Manor, a restored baroque manor house that is Lahemaa's most complete estate, and a walk along the boulder-covered coast near Käsmu, historically a village of sea captains and smugglers.
Return to Tallinn by early evening.
Day 7 — Tartu Day Trip & Final Evening
Tartu, Estonia's second city and its intellectual capital, is about 2.5 hours from Tallinn by direct bus or train — both comfortable and frequent, so no car needed. Tartu is built around its university, founded in 1632, and has an entirely different character from Tallinn: a compact, elegant old town, a lively student population, and a much slower pace.
Spend the morning around Town Hall Square and the university's main building, then walk up Toome Hill for the ruins of Tartu Cathedral and views over the Emajõgi River. The Estonian National Museum, on the city's edge, is one of the most ambitious museums in the Baltics — a sweeping account of Estonian culture and history in a striking modern building built into a former Soviet airfield runway.
Take an afternoon train or bus back to Tallinn (around 2.5 hours) in time for a final dinner. Spend it wherever you liked best over the week — the old town's cellar restaurants for atmosphere, or Kalamaja's newer kitchens for a more contemporary, and cheaper, send-off.