Itinerary - Georgia 360°: Exploring the Timeless Regions of the Caucasus

Welcome to Georgia! Our adventure begins in Tbilisi, a city of contrasts where East meets West and centuries-old charm blends with modern spirit. After arrival, check into the hotel and get to know your fellow travel group! Depending on timing, we may enjoy a gentle orientation walk along Rustaveli Avenue, past the glowing Bridge of Peace and into the heart of the Old Town. Tonight, we can join a dinner at a traditional Georgian restaurant, featuring local specialties like khinkali dumplings and khachapuri. For those up for it, Tbilisi’s nightlife offers live music, cozy wine bars, and rooftop views.

Today we leave the capital and journey deep into the lush Kakheti region, Georgia’s winemaking heartland. Our first stop is the peaceful Bodbe Monastery, where Saint Nino is buried. Next, we reach Sighnaghi, a cobbled hilltop town known as the “City of Love” with views over the Alazani Valley. Well have time to wander its charming streets, taste local wine, and enjoy a family-hosted lunch in a village winery. As we wind through the vineyards and valleys, we head to Telavi for the night, where the warm hospitality of eastern Georgia awaits.

After breakfast in Telavi, we journey north into the high Caucasus. Along the way, visit the Al. Chavchavadze House Museum in Tsinandali and the ancient Alaverdi Monastery. Driving through Tianeti, we stop to admire the emerald waters of the Jinvali Reservoir, explore Ananuri Fortress, and cross the spectacular Jvari Pass. Adventure lovers can try optional adrenaline activities in Gudauri: rafting, paragliding, quad biking or a jet boat ride. Finally, we reach Stepantsminda (Kazbegi), surrounded by soaring peaks and alpine beauty.

This morning, a 4WD takes us up to the iconic Gergeti Trinity Church, standing proud under Mount Kazbek. Later, we continue to Gveleti Waterfall, with a 550m trail if using an off-road vehicle or over 3km otherwise. For longer hikes, Truso Valley or Juta are amazing full-day options. In the afternoon, we return south visiting Mtskheta, the ancient capital, and the scenic Jvari Monastery. Nightfall brings us back to Tbilisi for a well-earned rest.

We venture deep into Georgia’s southern wilderness, starting with the dramatic Dashbashi Canyon, where the Diamond Bridge spans a chasm of breathtaking beauty. A short hike takes us down to the canyon floor for unforgettable views. From there, we drive past Paravani Lake through mountain landscapes toward the astonishing Vardzia Cave Monastery, a 12th-century city carved into stone. Expect some light climbing inside the complex. Our day ends in Akhaltsikhe, where medieval and modern cultures coexist.

This morning we explore Rabati Fortress, a multicultural citadel with Ottoman, Georgian, and Russian architecture. We then visit the lesser-known but magical Safara Monastery, nestled deep in the cliffs. The route continues into the green embrace of Borjomi, famed for its healing mineral waters. Walk the Central Park, taste spring water, or opt for a 4WD jeep tour into Borjomi-Kharagauli National Park, one of Europe’s largest protected areas. Tonight offers calm relaxation in a mountain town.

Our final road trip day takes us to the prehistoric Uplistsikhe Cave City, a rock-hewn marvel that once linked the Silk Road. Then, in Gori, we can visit Stalin’s childhood home and museum. On our way to Tbilisi, we can stop for an optional family-hosted lunch and cooking masterclass, to try our hand at baking khachapuri or making dumplings. Return to Tbilisi.

A relaxed final morning in Tbilisi gives you time to reflect, sip a last coffee, or do some last-minute shopping. Browse antiques at the Dry Bridge Market, or wander Vera and Sololaki’s leafy streets for hidden gems. Optional visits to the sulfur baths or final wine tastings round out the journey. With your backpack in hand and Georgia in your heart, we’ll say goodbye to an incredible trip full of memories (and flavors) that linger.