Rising 200m, this long and bluff plateau houses a honeycomb of caves and structures where people took refuge for centuries. It's wonderful to explore, especially (gingerly) the burial chambers and casemates with large open 'windows' in the vertiginous northern cliff. These are truly breathtaking, as is the view into the valley below.
First appearing in historical records as Kyrk-Or (Forty Fortifications), the city was settled sometime between the 6th and 12th centuries by Christianised descendants of Sarmatian tribes. The last powerful ruler of the Golden Horde, Tokhtamysh, sheltered here after defeat in the 1390s, and the first Crimean khanate was established at Chufut-Kale in the 15th century, before moving to nearby Bakhchysaray. After the Tatars left, Turkic-Jewish Karaites occupied the city until the mid-19th century, which won the mountain its current name of 'Jewish Fortress'.
Following the track from Uspensky Monastery, the best idea is to keep bearing right. The main entrance is not under the flat tin roof to the left of the Chufut-Kale sign, but further up the hill to the right. At this, the 14th-century main South Gate, you'll usually be hit for a 12uah entrance fee.
Soon after the gate, you enter a Swiss-cheese composition of carved-out rooms and steps. Behind this a stone path heads along the top of the plateau, past two locked kenassas (Karaite prayer houses) in a walled courtyard to the right. There is a Karaite cultural centre and cafe in the adjacent former house of the city's last resident, Karaite leader Avraam Firkovich.
To the left of the first intersection stands the red-tile roofed Muslim mausoleum (1437) of Dzhanike-Khanym, daughter of Tokhtamysh; to the right is an archway. Head left behind the mausoleum towards the cliff edge and enjoy the view into the valley below. To the right (east), a grassy track leads to two burial chambers in the northern side of the cliff.
From here it's hard to get lost; there are more caves until you reach the locked East Gate, where the road loops back on itself towards the main gate.