Arrive and settle into your hotel, then ease into the day with a leisurely stroll through Rustaveli Avenue, stopping for coffee at a local café before wandering down to the atmospheric narrow lanes of Sharden Street to browse artisan shops and galleries. Continue to the hillside Narikala Fortress via the cable car for panoramic views over the city, then descend to explore the sulfur bath quarter around Abanotubani, where you can peek into historic bathhouses or book a relaxing soak to recover from your travels.
Wander down to the lively Dry Bridge Market to hunt for Soviet-era memorabilia and local crafts, then enjoy a relaxed late lunch at a terrace restaurant in Rike Park with views of the modern Bridge of Peace. Afterward, take a gentle riverside stroll toward the cultural hub of Marjanishvili Square, stopping at a cozy café to sample traditional Georgian desserts like churchkhela while soaking up local street life.
As twilight falls, head to the atmospheric food-and-drink district around Meidani Square for a lively aperitif at a wine bar showcasing native Georgian varieties, then move on to a convivial dinner at a traditional restaurant in Anchiskhati to sample dishes like chakapuli and fresh khachapuri. After dinner, enjoy an evening concert or jazz set at the intimate G-Tower Cultural Center, followed by a slow riverside walk across the illuminated Metekhi Bridge to soak in the city lights and the view of Tbilisi's skyline.
Drive out of Tbilisi to the ancient capital and begin with a contemplative visit to Svetitskhoveli Cathedral, where you can admire its ornate frescoes and learn about the relics said to be housed there. From the cathedral, wander down to the riverside to see the stone-lined confluence and then pause for a late-morning Georgian coffee and local pastries at Mtskheta's historic Market Square café, watching daily life unfold in this UNESCO-listed town.
After a morning in the heart of Mtskheta, cross the river and take a short drive up to the hilltop Armazistsikhe Park for sweeping views of the town and the Aragvi-Mtkvari confluence, then stroll the peaceful paths to the nearby Samtavro Monastery to see its tranquil cloisters and centuries-old stonework. Return toward town for a late-afternoon tasting at Salobie's courtyard café, sampling homemade churchkhela and a warm cup of Georgian tea, then linger at Mtskheta Promenade to watch locals and pilgrims pass as golden light softens the ancient facades before heading back to Tbilisi.
As dusk falls, return toward Tbilisi but linger for a sunset aperitif on the terrace of Café Kala overlooking the river, sipping local white wine while the light softens the old town. For dinner, head to Tabla Rustaveli for a lively meal of grilled meats and regional salads, then finish the night with a relaxed digestif and live acoustic music at Fabrika's Bar, where the creative atmosphere offers a pleasant contrast to the day's historic sightseeing.
Set out early from Tbilisi along the Georgian Military Highway, stopping first at Ananuri Fortress to stretch your legs and admire its lakeside ramparts before continuing into the dramatic Caucasus foothills. Pause in the village of Gudauri for panoramic photos and a hearty local breakfast of cheese-stuffed khachapuri at a mountain kafé, then arrive in Stepantsminda to take the 4x4 up the dirt track toward Gergeti Trinity Church for a sunrise view of Mount Kazbek and a short, invigorating walk around the churchyard.
After your morning at Gergeti Trinity Church, take a scenic walk down into the village and stop for a warming lunch at Zakhele Guesthouse to taste mountain-style stews and homemade cheese while chatting with local hosts. In the afternoon, explore the dramatic Aragvi gorge on a guided hike to the lesser-known Dariali Gorge viewpoint, then visit the rustic Kobi village chapel and finish with a cup of herbal tea on the terrace of Rooms Hotel Kazbegi as you watch changing light sweep across Mount Kazbek.
As dusk settles over the mountains, enjoy a relaxed evening at Rooms Hotel Kazbegi's terrace bar with a glass of local orange wine while watching the alpenglow on surrounding peaks. For a convivial dinner nearby, walk to Khevi Gourmet for hearty regional dishes like beets-and-cheese salad and slow-braised lamb, then finish with live polyphonic singing at Local House of Culture or a nightcap beneath the star-filled Kazbegi sky.
Leave Tbilisi early for a scenic drive into Kakheti and begin with a guided cellar tour and qvevri tasting at Pheasant's Tears in Sighnaghi, where you'll learn about traditional clay-vessel winemaking and sample amber and red varieties. Continue with a stroll along the cobbled ramparts of Sighnaghi Fortress for panoramic vineyard views, then stop at the family-run Shalauri Wine Cellar to taste fresh grape must, try homemade cheese pairings, and chat with the vintners before heading toward Tbilisi for your departure.
In the afternoon, drive to the nearby Napareuli and join a tasting and cellar tour at Ramaz Nikoladze's Cellar, sampling qvevri-aged whites alongside a plate of local sulguni and sun-dried tomatoes while learning about indigenous grape varieties. Afterward, wander through the vine-lined lanes to the atmospheric estate of Schuchmann Wines for a guided vineyard walk, a light pairing of smoked trout and Georgian cheeses, and panoramic views before heading back toward Tbilisi for your evening departure.
Return toward Tbilisi but stop for a lingering sunset aperitif on the terrace of Vinotel, sampling a flight of small-producer qvevri wines paired with marinated eggplant and local goat cheese while the Kakheti hills glow golden. Back in the city, enjoy a farewell dinner at Caucasus Tavern, where a chef-led tasting menu highlights regional dishes with modern twists, then end the night with a digestif at Vino Underground-a cozy cellar bar offering rare Georgian vintages before your departure the next morning.