Georgia Highlights in 5 Days — Private Tour: Tbilisi, Kakheti & Kazbegi

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.

Once the capital of the ancient kingdom of Iberia, Mtskheta is where Georgia first embraced Christianity in the 4th century, and that legacy still shapes every street. A short drive from Tbilisi, this UNESCO-listed town pairs the soaring Svetitskhoveli Cathedral with the hilltop Jvari Monastery and the Samtavro convent, where St. Nino lived and King Mirian is buried (St. Nino herself rests at Bodbe in Kakheti). Come for the pilgrimage atmosphere, the icon-painting tradition, and a bowl of hearty lobio between the churches.

Rising above the Aragvi River, Ananuri is a fortified complex that once served as the stronghold of the Dukes of Aragvi, a feudal dynasty whose battles shaped this corner of Georgia. Within its walls stand two churches and a defensive tower, adorned with the intricate carvings and frescoes that define Georgian sacred art. From the ramparts, the view opens across the turquoise Zhinvali Reservoir and surrounding mountains, making it one of the country's most rewarding historical stops.

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.

Set against the snowcapped cone of Mount Kazbek, this 14th-century church is one of Georgia's most photographed sights and a living Orthodox pilgrimage site. We walk you up from Stepantsminda, about 60-75 minutes up through meadows that bloom with wildflowers in summer (about 430 meters of climb), or drive up the sealed road for those who'd rather save their legs. Once a refuge that safeguarded Georgia's religious treasures during invasions, it still holds travelers spellbound with its alpine isolation.

Uplistsikhe is a whole town carved into the rock above the Mtkvari River, and one of Georgia's oldest urban settlements. Walk among cave dwellings, a theatre-like hall, and tunnel passages that served as homes, temples, and gathering halls from the Early Iron Age, when this became a thriving pagan and later Christian center until the Mongol invasions. With its 9th-10th-century church and sweeping river views, it's an unhurried, hands-on encounter with ancient Georgian life etched directly into the cliffs.

Set in central Georgia, Gori is best known as the birthplace of Joseph Stalin, and its museum presents that legacy in an old-fashioned, uncritical way, from biographical exhibits to his personal railway carriage and a statue in the grounds. But the town has far deeper roots: it was fortified under King David the Builder, and it is still watched over by the hilltop ruins of Gori Fortress. Wander its lively markets, sample lobio and fresh sulguni, then continue to the nearby cave town of Uplistsikhe, about 20 minutes away.