Georgia in Winter — 6-Day Private Tour: Tbilisi, Kakheti & Gudauri Snow

King Vakhtang Gorgasali founded Tbilisi in the 5th century on the hot springs that still feed the domed sulfur baths of the Old Town. Climb to Narikala Fortress for panoramic views, wander the cobblestone alleys and ornate wooden balconies of Old Tbilisi, then cross the illuminated Bridge of Peace toward grand Rustaveli Avenue. Evenings bring khinkali, khachapuri, and wine from one of the world's oldest traditions, often paired with Georgian polyphonic singing.

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.

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.

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.

High in the Greater Caucasus, Gudauri is Georgia's biggest ski resort, with lifts rising from about 1,990 to 3,279 meters and a season that usually runs from late December to mid-April. When the snow melts, the same peaks open up to paragliders and hikers, with the Gudauri Viewpoint and a climb to Sadzele Peak rewarding you with panoramic mountain views. Cap each day with khinkali, khachapuri, and mulled wine, and a lively apres-ski scene warmed by genuine Georgian hospitality.

Stepantsminda, still widely called Kazbegi, is the base for Georgia's high Caucasus. The 14th-century Gergeti Trinity Church sits alone at 2,170 meters with Mount Kazbek—the country's third-highest peak at 5,054 meters—rising behind it. Reach the area on the 152 km drive from Tbilisi along the Georgian Military Highway (about 3-3.5 hours), then hike to the Truso Valley's mineral springs or walk the cliffs of the Dariali Gorge.