Spend your first day exploring Old Town. Tackle our walking tour in the morning and then stop for lunch in one of the city's many excellent eateries (Rataskaevu 16, just east of Town Hall Square, has great menu options). Spend your afternoon exploring one or two of the museums – perhaps the City Museum and the branch of the Estonian History Museum at the Great Guild Hall. In the evening, dress smart and head to posh Russian restaurant Tchaikovsky for dinner, finishing up in one (or two) Old Town bars.
The following day, do what most tourists don’t – step out of Old Town. Head to Kadriorg for a greenery-and-art fix and continue on to Maarjamäe to visit the museums and the war memorial. In the evening, hit the Rotermann Quarter for great food and bars.
Four days is enough to cover the remainder of central Tallinn's highlights, with more nights of eating and partying too. Round out your days with trips to relatively further-flung highlights such as the Lennusadam maritime museum, the Museum of Occupations, the Estonian Open Air Museum and the TV Tower. Allow some time to wander around the super-hip Telliskivi Creative City (a great place to eat and/or enjoy a restorative aperitif) and to explore the blooming Kalamaja neighbourhood, just beyond.