Moscow keeps its centuries stacked on top of each other: UNESCO convents from the Muscovite tsars, wooden estates where Ivan the Terrible grew up, Stalin's marble metro, and the Lubyanka's stone of remembrance. Three days, chronological.
Founded 1524 by Vasili III to mark the recapture of Smolensk, this UNESCO-listed walled convent later held Peter the Great's exiled half-sister Sophia. Smolensk Cathedral keeps 16th-century frescoes intact. Open 09:00–17:00.
Ivan the Terrible's childhood summer estate on a bluff above the Moskva. The white 1532 Church of the Ascension is Russia's first stone tented-roof church and a UNESCO site; Peter the Great's transplanted log cabin stands nearby.
Moscow's oldest surviving building stands here: the 1425 Spassky Cathedral, painted by Andrei Rublev, who is buried in the grounds. The monastery, founded 1357, now houses a museum of roughly 500 icons and Old Russian art.
A surviving pocket of 17th-century Moscow behind Taganka: the tiled Teremok gate of 1694, a covered bishops' walkway and a cobbled lane. Once the Moscow seat of the Sarai bishops, later a military prison that held Alexander Herzen.
Opened in 2015 on 1st Samotyochny Lane, the museum documents the Soviet camp system through original barrack doors, prisoner letters, maps of the camp archipelago and recorded survivor testimony across four floors.
A boulder shipped from the Solovki prison camp in 1990 sits facing the yellow-brick Lubyanka, headquarters of the Cheka, NKVD and KGB. Names of Moscow's executed have been read aloud at the stone each 29 October.
The Tagansky command post, 65 metres beneath Kotelnichesky Lane, was the 1950s nuclear-war reserve headquarters for Soviet long-range aviation. Guided tours cover the tunnels, communications room and a mock launch drill.
Vera Mukhina's 24-metre stainless-steel pair, built for the 1937 Paris Expo, guards the entrance to VDNKh — the 1939 exhibition city of gilded fountains, rocket pavilions and one pavilion per Soviet republic.
Ride the 1935 metro as a museum: Mayakovskaya's steel arches and Deineka ceiling mosaics, Novoslobodskaya's stained glass, Komsomolskaya's baroque hall and the 76 bronze figures of Ploshchad Revolyutsii.
The white stone merchant house granted by Ivan the Terrible to English traders in 1556 is Moscow's oldest surviving secular building. Inside are the vaulted treasury and an English hearth; five old churches line Varvarka outside.
Flat 50 at Bolshaya Sadovaya 10, where Mikhail Bulgakov lived from 1921 and where the devils of The Master and Margarita lodge, is now a museum of his manuscripts and 1930s furnishings. The ponds ten minutes away open the novel.
Moscow's oldest named street, recorded in 1493, rebuilt as an aristocratic quarter after the 1812 fire and later the bohemia of bard Bulat Okudzhava, whose statue stands near No. 43. Pushkin's 1831 flat is at No. 53.