An Affair with Georgia: Wine, Mountains & Timeless Charm

Ease into Georgia with a day that feels like stepping into a storybook. Wander through the heart of Old Tbilisi, where pastel balconies, winding lanes, and hidden courtyards set the tone for the week ahead. Start your day with a relaxed exploration of the Old Town. Think charming streets, local art corners, and that slightly chaotic, lived-in beauty that makes Tbilisi so special. Make your way to the cable car station and glide up to the iconic Narikala Fortress. The views from the top are unreal, sprawling cityscapes, the river cutting through, and layers of history all at once.

Head back down and take your time soaking it all in. Stop for coffee, browse boutiques, and just let the city unfold at its own pace. Recharge at a private suite in the Abanotubani Sulphur Baths.

For lunch, I’d recommend Cafe Leila—a beautiful, almost whimsical space known for its vegetarian-friendly menu and relaxed vibe.

In the evening, make your way to Shavi Lomi for dinner. It’s one of those places that perfectly blends traditional Georgian flavors with a modern, understated setting, which is ideal for your first night.

Start your morning at the iconic Dry Bridge Market—a treasure trove of vintage finds, Soviet-era memorabilia, and quirky antiques. Even if you don’t buy anything, it’s an experience in itself.

From here, head towards Rustaveli Avenue for a more polished side of the city. Think grand architecture, cultural landmarks, and a slightly more cosmopolitan vibe. You can dip into museums, pop into bookstores, or just enjoy a slow walk soaking in the contrast from Old Town.

By afternoon, make your way to Fabrika Tbilisi—a repurposed Soviet factory turned into one of the coolest creative spaces in the city. This is where Tbilisi’s younger, artsy energy really comes alive. Grab a coffee, explore the courtyard filled with street art, and just sit back for a bit.

Discover Tbilisi’s vibrant electronic music scene at Bassiani, an iconic club, or go to Lolita to experience nightlife.

Drive out to the Kakheti region, where rolling vineyards stretch endlessly and the pace of life instantly softens. Your first stop is the postcard-perfect town of Sighnaghi, often called the “City of Love.” Think cobbled streets, pastel houses, and sweeping views over the Alazani Valley.

Take your time wandering through the town, stopping for photos, little cafés, and just soaking in the charm. From here, head out for a traditional Georgian wine experience-this is, after all, one of the oldest wine regions in the world.

Visit a local winery for a relaxed tasting session, where you’ll be introduced to Georgia’s unique winemaking style using qvevri (clay vessels). Expect bold flavors, generous pours, and that signature Georgian hospitality.

Lunch here is an experience in itself is long, leisurely, and paired perfectly with local wines and rustic dishes.

Today is less about the destination and more about one of the most scenic drives you’ll ever take. Begin your journey along the iconic Georgian Military Highway, easily one of the most scenic drives in the region. The landscapes shift effortlessly, from cityscapes to rolling hills, and before you know it, you’re deep in the Caucasus.

Make a stop at the stunning Ananuri Fortress, set dramatically against a turquoise reservoir. This is one of those views that feels almost unreal.

Continue onward through Gudauri, pausing at panoramic viewpoints where the mountains stretch endlessly. The air feels different here—crisp, quieter, almost grounding.

By the time you reach Kazbegi, the pace naturally slows. Check in, unwind, and let the stillness of the mountains take over.

Start your morning with a visit to the iconic Gergeti Trinity Church. Perched dramatically against the backdrop of Mount Kazbek, it’s one of those views that feels almost surreal. Aim to go early, before the crowds.

If you’re in the mood to explore, Kazbegi offers plenty of light hikes and scenic trails. Nothing too intense, just enough to immerse yourself in the landscape, breathe in the crisp mountain air, and take it all in.

You can also drive out towards the stunning Dariali Gorge, where towering cliffs and rugged terrain create a completely different, more dramatic side of the region.

The rest of the day is intentionally slow. Spend time at your hotel, soak in the views, maybe enjoy a long lunch or just sit with a coffee and do absolutely nothing.