Kakheti Grape Harvest (Rtveli) — 2-Day Private Trip with a Night in Sighnaghi

A walled hilltop town in Kakheti's wine country, Sighnaghi keeps one of Georgia's best-preserved fortress walls, whose 23 towers look out over the vineyard-covered Alazani Valley toward the Caucasus. Walk the ramparts, taste qvevri wine made the ancient way at Pheasant's Tears, and see Niko Pirosmani's paintings in the town museum. Nearby Bodbe Monastery holds the tomb of St. Nino, drawing pilgrims to its hillside gardens.

A short drive from Sighnaghi, Bodbe Monastery holds the tomb of St. Nino, who brought Christianity to Georgia in the 4th century; the church standing today goes back to the 9th. Walk the rose gardens, take in the wide Alazani Valley views, and follow the path down to St. Nino's Spring, long visited for its healing waters. The small monastery museum fills in the rest of this enduring pilgrimage site.

In the heart of Kakheti, Tsinandali centres on the elegant Chavchavadze Estate of the poet Alexander Chavchavadze, who built a winery here in the 1830s that blended European and Georgian methods. Stroll the English-style gardens, tour the house museum, and descend into the enoteca, whose collection holds bottles from 1814, including the famous 1841 Saperavi. With concerts and harvest celebrations through autumn, it pairs aristocratic history with the easy pleasures of Georgian wine country.

Winding through the Gombori Range on the old travel route between Tbilisi and the wine country of Kakheti, Gombori Pass turns the drive itself into the destination. The road climbs past forests, open viewpoints over valley and mountain, and small villages where shepherds still work the slopes. Stop at a roadside stall for fresh bread, cheese and local honey, and time your visit for spring or early summer when wildflowers cover the hillsides. Telavi's vineyards sit just half an hour east.