A one-week journey from the cobbled streets of Tbilisi to the peaks of Kazbegi and the vineyards of Kakheti where Europe and Asia meet over wine, mountains, and centuries of tradition
Wedged between the Black Sea and the snowy Caucasus, Georgia has been a crossroads of empires for over two millennia. Orthodox churches overlook Soviet mosaics; medieval watchtowers share skylines with brutalist relics and modern glass bridges.
This week-long loop from Tbilisi takes you through the country’s spiritual and natural heart. Wander the capital’s crooked streets and bathhouses before tracing the Georgian Military Highway north to the mountains of Kazbegi, where ancient monasteries perch on misty peaks. Then, head east into Kakheti, Georgia’s wine country, where 8,000 years of winemaking heritage still survives in clay qvevri buried underground.
It’s a short trip, but Georgia’s rhythm, the slow toasts, long drives, and mountains that seem to swallow sound, lingers long after you leave.
Kazbegi's Peaks & Monasteries
In heart of the High Caucasus, visit the Gergeti Church, which stands watch beneath snow-capped Mount Kazbek on the border with Russia, and hike to Gveleti Waterfalls
Kazbegi's Peaks & Monasteries
In heart of the High Caucasus, visit the Gergeti Church, which stands watch beneath snow-capped Mount Kazbek on the border with Russia, and hike to Gveleti Waterfalls
Kakheti, Birthplace of Wine
Tbilisi's contrasts
Arrive in Tbilisi, Georgia’s soulful capital straddling the Kura River. The city feels like a living palimpsest, with Persian fortresses, Orthodox cathedrals, and Soviet mosaics all within a few minutes’ walk.
Start with the Old Town, winding through alleys of crumbling pastel houses and wrought-iron balconies. Visit the Narikala Fortress for views across the city, and descend to the Abanotubani sulphur baths, where warm mineral pools have soothed travellers since the Silk Road era.
In the evening, dine at Stamba, Shavi Lomi, Alubali, Keto & Kote, or Iasamani, for modern Georgian cuisine and a glass of amber wine, the country’s signature style, fermented with grape skins in earthenware pots.
Just 30 minutes north lies Mtskheta, once the capital of the ancient Iberian kingdom and still Georgia’s spiritual heart. Visit the Jvari Monastery, built in the 6th century on a mountain top overlooking the confluence of the Mtkvari and Aragvi rivers. Below it sits Svetitskhoveli Cathedral, where legend says Christ’s robe is buried beneath the altar.
The two churches are UNESCO World Heritage Sites and mark the adoption of Christianity here in the 4th century, one of the earliest in the world.
Have lunch at one of the riverside restaurants serving khinkali (dumplings) and lobio (bean stew) in clay pots before returning to Tbilisi.
Head north along the Georgian Military Highway, a spectacular route through mountains and valleys once used by traders and invaders moving between Russia and the Caucasus. Stop at the Ananuri Fortress, a 17th-century complex overlooking the turquoise Zhinvali Reservoir, then continue to the Soviet-era mosaic viewpoint near Gudauri, depicting Georgian-Russian friendship in wild colours.
Pause for roadside khinkali before reaching Stepantsminda (Kazbegi), set beneath Mount Kazbek (5,047m). Check into the Rooms Hotel, a modern mountain lodge with panoramic views, and spend the afternoon hiking to the Shdugra Waterfalls or driving to the Dariali Gorge, a dramatic canyon marking the edge of Europe.
Before leaving, hike or drive up to Gergeti Trinity Church, perched 2,000m high with Mount Kazbek towering behind. Built in the 14th century, it became a symbol of Georgia’s faith and endurance through centuries of invasion.
Descend from the mountains and return to Tbilisi by evening, stopping for coffee or fruit stalls along the way. Reward tired legs with a soak in one of the historic sulphur baths, the same ones that gave the city its name (“Tbilisi” comes from tbili, meaning warm).
Spend another day exploring Tbilisi’s contrasts. Start with the Dry Bridge Market, a maze of Soviet antiques and family heirlooms, then wander through Vera or Sololaki, districts filled with 19th-century mansions and hidden courtyards.
For art lovers, the Tbilisi History Museum and Chronicle of Georgia Monument offer a crash course in national identity, half mythology, half memory.
Dinner at Barbarestan, where recipes from a 19th-century duchess’s cookbook are reimagined with local ingredients, or head to Fabrika, a Soviet sewing factory turned creative hub, for live music and street food.
Drive east into Kakheti, Georgia’s oldest winemaking region, where vineyards stretch to the horizon. Stop first at the 11th-century Alaverdi Monastery, whose monks have been making qvevri wine for over a millennium, then visit a local cellar for a tasting.
Continue to Sighnaghi, a hilltop town encircled by defensive walls overlooking the Alazani Valley. Visit Pheasant’s Tears or Okro’s Wines, both pioneers of Georgia’s natural wine revival.
Stay overnight at Schuchmann Wines Chateau, a winery where each stay comes with a wine tasting as well as a wine massage!
In the morning, visit Bodbe Monastery, where St. Nino, the woman who converted Georgia to Christianity, is buried. Drive on to Tsinandali, once the estate of poet-prince Alexander Chavchavadze, now a museum and winery that introduced European-style winemaking to Georgia in the 19th century.
Enjoy lunch nearby, Shota’s or one of the family-run roadside khinkali spots, before returning to Tbilisi for one last evening stroll through the capital’s glowing streets.
- Transport: Best done by rental car or private driver as public transport is limited between small towns
- Season: Late spring and early autumn offer clear skies and mild temperatures
- Food Tips: Try khachapuri (cheese bread), mtsvadi (grilled meat skewers), and churchkhela (walnut candy).
"Driving the Military Highway really did feel like stepping through Georgia’s past, from ancient fortresses to Soviet mosaics, as well as its present, with Russian commerce lorries winding down arduous roads for trade and Chinese construction sites working on infrastructure mega projects, all surrounded by unreal mountains."
"Kakheti was my favourite part, the light, the vineyards, and the local community sense that wine here isn’t just a drink, it’s a cultural asset that’s been part of the history for 8,000 years. The staff at Schuchmann Wines Chateau defiantly exemplify this."
"The food alone was worth the trip, khinkali and khachapuri for days on end is something I could've kept going with, especially given the slight variations between places, and the fact that people treated every meal like a celebration"
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