Damascus has been inhabited continuously for four millennia and its layers are all still legible: Roman gates, Ayyubid tombs, Ottoman khans, an Ottoman railhead. Three days of walking reads that sequence in the order it was built.
Syria's archaeological treasury holds the Ugarit tablet bearing the world's first alphabet, the Dura-Europos synagogue reassembled wall by wall, and Palmyrene funerary busts. The gateway is the Umayyad facade of Qasr al-Hayr al-Gharbi.
Six Corinthian columns and a broken pediment mark the western gate of the 1st-century Roman temple whose temenos ran 380m across. Diocletian enlarged it; the Byzantines raised the Basilica of St John inside the same enclosure walls.
Al-Adil's Ayyubid fortress of 1203–1216 is the rare Middle Eastern citadel built on flat ground rather than a spur, with twelve square towers and a moat fed by the Barada. Saladin's equestrian statue stands at its northwest corner.
The only Roman gate of Damascus surviving intact, its triple arch dated to the 3rd century: a wide central span for carts, two narrow flanking ones for pedestrians. The bell tower above was added by the Greek Catholic parish in 1867.
The 1913 terminus of the Ottoman pilgrimage line to Medina, designed by Fernando de Aranda with a carved cedar ceiling and stained glass. Lawrence's raiders cut its southern track in 1917; an early steam locomotive stands outside.
On 6 May 1916 Jamal Pasha hanged Arab nationalist leaders here, giving the square its second name. At its centre stands the 1907 bronze Telegraph Monument, topped by a model of the Medina mosque marking the Damascus–Hejaz line.
Mimar Sinan's complex of 1554–1560 for pilgrim caravans: alternating black basalt and white limestone courses, twin pencil minarets and a lead-domed prayer hall. The adjoining madrasa now holds Ottoman and Mandate-era weaponry.
Salah ad-Din died in Damascus in 1193 and lies in a walnut cenotaph against the Umayyad Mosque's north wall. The white marble sarcophagus beside it was a gift from Kaiser Wilhelm II after his 1898 visit; the wooden one is the actual grave.
A stone cellar five metres below today's street, held to be the house where Ananias restored Saul's sight. The masonry is 1st-century Roman; the vaulted chapel above it is Byzantine with Crusader-period repairs, deep in the Christian quarter.
The largest caravanserai in the Old City, built in 1751–52 by governor As'ad Pasha al-Azm: nine domes carried on eight granite piers above a central fountain, merchants' cells along the gallery, and striped ablaq stonework throughout.
This quarter on Qasioun's lower slope was founded by refugees fleeing Crusader Jerusalem in the 1150s and holds dozens of Ayyubid madrasas. Ibn Arabi, the Andalusian mystic who died here in 1240, lies beneath a dome raised by Selim I in 1518.
The ridge where four millennia of city plan read at once: the Ghouta oasis to the east, the Old City grid around the Umayyad Mosque, the Salihiyya minarets directly below. Local tradition sets the Cain and Abel story in the Cave of Blood here.