Telavi is the capital of Kakheti, a town of about twenty-two thousand people that serves as the regional hub for wine, farming and old-fashioned Georgian hospitality. It sits on the northwest side of the Alazani valley, with the Tsiv-Gombori range behind and, on a clear day, the white wall of the Greater Caucasus ahead across the plain. It is a good place to stop, with real shops and a real market, and with enough history to keep you interested between mouthfuls.
For centuries this was the seat of the Kakhetian kings, and the town's most famous ruler was Erekle II, who in the eighteenth century united Kakheti with neighbouring Kartli and then, under growing pressure from Persia, turned to Russia for protection. His palace, Batonis Tsikhe, still stands in the old town, and a large statue of him on horseback looks over the main square. A short walk away is a huge plane tree said to be around nine hundred years old, with a trunk wide enough that people shelter inside the hollow. It is not hard to find, and it is more impressive than it sounds.
The riding around Telavi is gentler than in the mountains. The plain is a patchwork of vineyards, orchards and maize, the roads are straight and usually in decent shape, and the pace is relaxed. Watch out for tractors, horse carts and the odd flock crossing, and treat any road on market day with respect. Nearby are the wine estates of Tsinandali, where the Chavchavadze family hosted poets and nobles in the nineteenth century, and the fortified church complex at Gremi, a former royal town.
As a rest stop, Telavi is excellent. Fuel is easy to find, there are plenty of cafes serving mtsvadi, the grilled pork skewers that every Georgian cook argues about, plus fresh bread from a tone, the clay oven, and several wine bars and cellars if you are staying the night. Guesthouses are cheap and friendly. If you are coming off the Gombori ridge or heading up toward the Caucasus passes, this is where you gather yourself, eat well and refill the tank for the next section.