Toompea Castle & Viewing Platforms – Skip the crowded Kohtuotsa platform and head to the lesser-known Patkuli viewing point for equally stunning vistas without the tour groups.

St. Olaf’s Church Tower – Visit during the first hour of opening to avoid both the crowds and the afternoon winds that occasionally cause tower closures.

Telliskivi Creative City – The weekend flea market is tourist-heavy, but Thursday evenings offer locals-only jazz performances in the F-hoone courtyard.

Estonian Open Air Museum – The traditional smoke sauna demonstrations happen only on Wednesday afternoons, with the opportunity to sample Estonian sauna whisks rarely shown to tourists.

Kadriorg Palace & Park – The hidden Japanese garden behind the palace is most spectacular during mid-May when the cherry blossoms peak two weeks after those in Western Europe.

Patarei Prison – Book the extended tour with former guards who reveal unscripted stories about Soviet-era imprisonment not mentioned in the official exhibits.

Lennusadam Seaplane Harbor – The submarine Lembit can be explored with almost no restrictions early Tuesday mornings when museum staff conduct maintenance checks.

Kalamaja District – The wooden houses with colorful doors are Instagram-famous, but locals know the true hidden gems are the interior courtyards accessible through Vabriku Street.

Town Hall Pharmacy – Beyond the medieval apothecary exhibits, ask for the special herbal liqueur tasting that happens in the basement laboratory every afternoon at 3pm.

Balti Jaama Market – Bypass the ground floor food hall and head directly to the third floor where elderly Estonian women sell hand-knitted wool items at half the price of Old Town souvenir shops.