5 Days – Grand Classic

Uplistsikhe was already ancient when Christianity arrived: a whole town of halls, sanctuaries, wine cellars and a theatre cut into a sandstone ridge above the Mtkvari, inhabited from the early first millennium BC. Caravans of the Silk Road watered here, and pagan priests read fortunes in its smoke-blackened chambers. You wander freely between the caves, climbing to a basilica that crowns the rock. Sunset turns the whole hillside honey-gold.

In the 12th century Queen Tamar's builders carved an entire city into a cliff above the Mtkvari: thirteen floors of dwellings, chapels, refectories and wine cellars, home to thousands of monks. An earthquake later sliced the mountain open, exposing the honeycomb you climb through today. Frescoes from Georgia's golden age still glow in the rock-cut Church of the Dormition. Walking its tunnels and stairways, with swallows wheeling over the valley below, feels like entering a legend that happens to be real.

Rabati Castle in Akhaltsikhe is a city within walls: a Georgian church, an Ottoman mosque, a synagogue quarter, gardens, towers and a keep, restored into one fairytale labyrinth. Every staircase opens a new courtyard; every rampart a new view over the town and hills. The mix of styles tells the true story of Georgia's south, where empires met for centuries. Come late in the day, when the stone glows and the crowds thin.

Sighnaghi sits on a hilltop ringed by a complete 18th-century wall: 23 towers and four kilometres of battlements you can actually walk. Below the pastel lanes and carved balconies, the Alazani Valley spreads out toward the snow wall of the Caucasus. The town's marriage house works around the clock, which is how Sighnaghi earned its nickname, the 'city of love'. Add nearby Bodbe Convent, resting place of St Nino, and you have Kakheti's most romantic stop.

Georgians have been making wine for at least 8,000 years, and in Kakheti the method has never changed: fermentation in qvevri, great clay vessels buried in the earth, now protected by UNESCO. Family cellars pour amber and ruby wines you will simply not taste anywhere else. Between tastings rise some of the country's greatest monuments: Alaverdi's soaring cathedral, fortified Gremi, hilltop Nekresi. Come hungry, because the Kakhetian table is Georgia's most generous.