Explore Kakheti: Georgia's Wine Country and Its Mountains

Sighnaghi is the town visitors picture: an eighteenth-century defensive wall still ringing a hillside of narrow lanes and wooden balconies, with long views across the Alazani valley to the snow line. It is small enough to walk in an hour and pleasant enough to stay in for two nights, and the surviving stretch of town wall can be walked for the views. Telavi is the opposite and just as useful — a genuine regional town rather than a preserved one, with a market, a fortress and the practical infrastructure that makes it the sensible base for exploring the valley. Between them lie the village-scale places that give the region its texture, along with Bodbe monastery just outside Sighnaghi, a working convent in a cypress garden with a spring below it. Staying in the valley rather than commuting to it is the single decision that changes the trip, because Kakheti's evenings are the point.

Kakheti's wine is made at every scale, and the range is the reason to spend time here rather than visit one estate. Larger producers run proper tasting rooms with English-speaking staff; village families make wine in buried qvevri in the yard and pour it at a kitchen table. Both are worth doing and they are different experiences, not better and worse versions of one. The monasteries are the region's other layer and considerably older: Alaverdi, whose cathedral stood as the tallest building in Georgia for centuries and whose monks still make wine; Ikalto, a monastic academy in an overgrown garden; and the ruined royal complex at Gremi standing alone above the plain. If your dates allow it, come for rtveli, the September grape harvest, when the whole valley turns into a working festival and visitors staying in village guesthouses are routinely handed a bucket and drawn into it — comfortably the best reason to let the dates decide the itinerary.

Administratively Tusheti belongs to Kakheti; in every other respect it belongs to another country. It is a high province of stone villages, defensive towers and summer pastures on the far side of the Greater Caucasus, and it is reached by the Abano Pass — an unpaved mountain road that climbs above the tree line, is generally open only through the summer months, and is closed by snow the rest of the year. It is not a drive to attempt in a standard hire car or without a driver who knows it; shared four-wheel-drive transfers are the normal way in and are arranged locally. What is at the other end is one of the least-changed inhabited landscapes in the Caucasus: Omalo and the villages above it, tower houses, shepherds moving flocks that still walk to and from the lowlands each year, and walking between settlements as the main activity. It requires several days and it is the strongest argument in Kakheti for planning around your dates rather than your wishlist.