Day 1: Welcome to Tbilisi

Arrive at Tbilisi International Airport

Your driver meets you at the airport and transfers you to your hotel in the heart of the old city. After settling in, we begin with a leisurely walking tour through Tbilisi’s atmospheric streets.

We’ll explore the Metekhi Plateau, where a 13th-century church overlooks the Mtkvari River and offers your first panoramic view of the city’s famous blend of old and new. Wander through the sulfur bath district—Tbilisi literally means “warm place” in Georgian, named for the hot springs that bubble beneath the streets. If you’d like to experience a traditional scrub-down at the historic Orbeliani Baths, we can arrange an evening session.

The day ends with a welcome dinner at a local restaurant, where you’ll taste your first Georgian wines alongside classics like khinkali (soup dumplings), khachapuri (cheese bread), and fresh herb-laden salads.

Overnight: Tbilisi (3-star hotel or boutique guesthouse)
Meals: Welcome dinner

Day 2: Ancient Capitals & Mineral Springs

Mtskheta → Gori → Uplistsikhe → Borjomi

We leave Tbilisi early and drive 20 minutes north to Mtskheta—Georgia’s ancient capital and spiritual heart. Two UNESCO World Heritage Sites await: Jvari Monastery, perched on a hilltop with commanding views of where the Aragvi and Mtkvari rivers meet, and Svetitskhoveli Cathedral, where tradition holds that Christ’s robe is buried beneath the floor.

From here, we head west to Gori, birthplace of Joseph Stalin. The controversial Stalin Museum offers a fascinating glimpse into Soviet history (optional visit). More compelling for most visitors is our next stop: Uplistsikhe, a cave city carved into volcanic rock over 3,000 years ago. Walking through its ancient streets, theaters, and temple chambers, you’ll understand why this was once a major stop on the Silk Road.

We arrive in Borjomi by late afternoon. This elegant spa town, nestled in a forested gorge, has been famous for its mineral water since the 19th century. Stroll through Borjomi Central Park and taste the naturally carbonated water straight from the spring—an acquired taste, but one that Georgians swear by.

Overnight: Borjomi (guesthouse)
Meals: Breakfast, dinner
Driving: Approximately 3.5 hours total

Day 3: Cave Cities & Medieval Fortresses

Vardzia → Khertvisi → Rabati Castle → Akhaltsikhe

Today we venture into Samtskhe-Javakheti—a region of dramatic gorges, highland plateaus, and layered history where Georgian, Armenian, Turkish, and Russian influences intertwine.

The morning’s highlight is Vardzia, a 12th-century cave monastery that once housed 2,000 monks across 13 levels carved into a sheer cliff face. Queen Tamar herself used this as a stronghold during Georgia’s Golden Age. Your guide will lead you through the labyrinthine tunnels, past the Church of the Dormition with its original frescoes, and explain how this complex functioned as a self-sufficient city with bakeries, wine cellars, and an irrigation system.

We stop at Khertvisi Fortress—one of the oldest in Georgia—before reaching Akhaltsikhe. Here, the restored Rabati Castle complex showcases the region’s multicultural heritage: a Georgian church, a Turkish mosque, and a synagogue stand within the same walls.

Dinner tonight features Meskhetian cuisine—distinct from the rest of Georgia, with influences from centuries of Turkish rule.

Overnight: Akhaltsikhe (hotel or guesthouse)
Meals: Breakfast, dinner
Driving: Approximately 2.5 hours total

Day 4: Journey to Wine Country

Akhaltsikhe → Tbilisi → Signagi

We retrace our route through Borjomi and Tbilisi, but the real destination today is Kakheti—the cradle of wine civilization. As we cross the Gombori Pass, the landscape transforms: terraced vineyards stretch toward the horizon, backed by the snow-dusted peaks of the Greater Caucasus.

Our destination is Signagi, the “City of Love.” This small hillside town is famous for its fully preserved 18th-century defensive walls (you can walk the entire 4km circuit) and its 24-hour wedding registry—couples from across Georgia elope here on a whim.

We check into our guesthouse and take an evening stroll through Signagi’s cobblestone streets. From the town walls, you’ll watch the sun set over the Alazani Valley—an ocean of vineyards stretching to the mountains. This is the view that has inspired Georgian poets for centuries.

Overnight: Signagi (boutique guesthouse with valley views)
Meals: Breakfast, dinner
Driving: Approximately 4 hours total

Day 5: Wine, Wine & More Wine

Signagi → Velistsikhe → Pheasant’s Tears → Tsinandali

This is the day wine lovers have been waiting for. After breakfast overlooking the valley, we begin our deep dive into Kakhetian winemaking.

First stop: the Signagi Museum, home to an excellent collection of archaeological artifacts and—most importantly—a wine cellar offering tastings of local varieties like Saperavi and Rkatsiteli.

Next, we visit Pheasant’s Tears in the village of Signagi—one of Georgia’s most celebrated natural wine producers. American-born painter John Wurdeman founded this winery after falling in love with Georgian winemaking traditions. Here you’ll taste wines fermented in qvevri (clay vessels buried underground) using methods unchanged for 8,000 years. UNESCO recognized this tradition as Intangible Cultural Heritage—and one sip tells you why.

In Velistsikhe village, we explore a 16th-century wine cellar that’s been in the same family for generations. This isn’t a commercial winery—it’s a working family cellar where you’ll taste homemade wines and learn the difference between Kakhetian and European styles.

Our final stop is Tsinandali Estate—the ancestral home of the Chavchavadze princes, who pioneered European-style winemaking in Georgia. The cellar contains bottles from as far back as 1841. We tour the romantic gardens, taste their signature white blend, and learn how this estate shaped Georgia’s wine history.

Overnight: Telavi area (guesthouse or boutique hotel)
Meals: Breakfast, wine-paired lunch, dinner
Wine tastings: 15+ wines across 4 locations

Day 6: Monasteries, Silk Road & Chacha

Gremi → Nekresi → Ikalto → Telavi

Today we explore Kakheti’s rich cultural heritage beyond the wineries.

We start at Gremi, the former capital of the Kakhetian Kingdom. The 16th-century royal citadel and Archangel Church stand as reminders of the Silk Road wealth that once flowed through this valley. Merchants from Persia, India, and China passed through these gates carrying spices, silk, and gems.

Nekresi Monastery requires a short shuttle ride up a steep mountain, but the 6th-century complex and sweeping valley views make it worthwhile. This is one of Georgia’s oldest Christian sites—and one of the least crowded.

At Ikalto Academy, you’ll walk the grounds where 12th-century scholars developed the world’s first formal curriculum for winemaking. Some historians believe the legendary poet Shota Rustaveli studied here. The atmospheric ruins include the original wine presses.

Lunch today is special: at Nikala Restaurant in Telavi, you’ll be introduced to chacha—Georgian grape brandy. Your host explains the distillation process while you sample different strengths and ages. (Don’t worry—we pace the tastings carefully, and dinner will soak everything up.)

Overnight: Telavi area (same guesthouse)
Meals: Breakfast, lunch with chacha tasting, farewell supra dinner

Day 7: Final Discoveries & Departure

Telavi → Ujarma → Tbilisi

After a leisurely breakfast, we begin our return to Tbilisi via the scenic Gombori Pass. Our final cultural stop is Ujarma Fortress—a 5th-century stronghold where King Vakhtang Gorgasali once ruled. The atmospheric ruins offer a quiet moment of reflection before we rejoin modern life.

We arrive in Tbilisi by early afternoon, giving you time for last-minute shopping at the Dry Bridge Flea Market, a final stroll through the old town, or a relaxing meal before your departure.

Transfer to Tbilisi International Airport for your onward journey—or extend your stay to explore more of Georgia.

Meals: Breakfast
Driving: Approximately 2.5 hours