Begin your first morning easing into Tbilisi with a leisurely stroll and coffee at Fabrika, the vibrant former soviet sewing factory turned creative hub, then wander down to the colorful facades of Sharden Street to soak up local life and boutique shops. Continue to the nearby riverfront to ride the cable car up to Narikala Fortress for sweeping views, then descend through the peaceful Botanical Garden for a gentle introduction to Georgia's landscapes and history.
After lunch, wander Tbilisi's atmospheric lanes toward Sioni Cathedral to glimpse centuries-old Georgian Orthodox art, then browse the nearby stalls at Meidani (Sololaki) Market for local snacks and souvenirs. Continue with a relaxed riverside walk to the modern Bridge of Peace and take a short funicular ride up to Mtatsminda Park for panoramic city views, a coffee or pastry at the hilltop café, and gentle rides that ease you into the rhythm of the city.
As twilight settles, head to Leselidze Street for lively bars and people-watching, then step into the cozy wood-paneled atmosphere of Café Gabriadze to catch a relaxed puppet-clock show and sip Georgian mulled wine. Finish the night with a short stroll to Anchiskhati Basilica's quietly illuminated façade and then dine at a nearby family-run restaurant like Puri Guliani, where you can taste traditional khachapuri and warm supras in a welcoming, local setting.
Start your morning with a hearty Georgian breakfast at the charming Café Leila in the historic Sololaki quarter, then stroll to the ornate Anchiskhati Basilica to admire early medieval frescoes and tranquil churchyard light. From there, wander up to the striking modern silhouette of Holy Trinity Cathedral (Sameba) for sweeping city views and peaceful cloistered grounds, finishing with a restorative soak in one of the classic Abanotubani sulfur bathhouses-choose a private room at Orbeliani Baths for a traditional scrub and warm herbal infusion to relax after your first day of exploring.
After a relaxed morning, head to Rustaveli Avenue for people-watching and a peek inside the ornate Georgian National Opera and Ballet Theater, then pop into the nearby Tbilisi Art Gallery to see contemporary Georgian works. Continue to the lively Dry Bridge Flea Market to hunt vintage Soviet-era finds and local crafts, then warm up with a late-afternoon treat of spicy khinkali at a neighborhood eatery before returning to soak in a private room at the classic Gulo's Baths for a restorative scrub and herbal steam.
As dusk deepens, wander the lantern-lit lanes of Sololaki toward the elegant terrace of Rooms Hotel Bar, where you can sip a craft cocktail and watch the city lights come alive. For a lively local supper afterward, head to Barbarestan for refined takes on Georgian classics, then finish with a nightcap at the intimate jazz cellar of Fabrika's Bar or a cozy rooftop view from Stamba Hotel's terrace to close the day with warm conversation and skyline panoramas.
Catch an early minibus or private driver from Tbilisi to Mtskheta and begin by exploring the UNESCO-listed Svetitskhoveli Cathedral, where you can admire its frescoes and the revered royal burial site while a local guide explains its place in Georgian Christian history. From there, stroll the peaceful lanes to the riverside and visit the intimate Samtavro Monastery for a calm chant-filled moment, then cross the bridge to board a short riverboat or walk up through olive trees toward the hilltop Jvari Monastery to watch the sunrise light spill over the confluence of the Aragvi and Mtkvari rivers-perfect for photos and a contemplative coffee from a nearby kiosk.
After the morning's hilltop calm, descend toward the riverside and enjoy a leisurely lunch at Salobie Bia where you can taste homemade lobio and freshly baked mchadi while watching local life by the water. Spend the afternoon wandering the cobbled streets to visit the atmospheric Armazis Tsikhe (Armaziani House) museum to learn about royal Georgian domestic life, then stroll to the scenic Svetitskhoveli Square's surrounding cafes and stop at Cafe Mtskheta for strong Georgian coffee before a relaxed riverside walk along the Mtkvari to soak in the confluence views and local artisan stalls.
After returning from the hilltop calm, linger in Mtskheta for a peaceful early evening at Kremlin Garden Café, enjoying a cup of strong Georgian coffee and walnut baklava while watching the light fade over the river. Then stroll to the riverside promenade and catch a short horse-drawn carriage ride to Mtskheta Terrace for golden-hour views, before settling into a cozy dinner at Salobie Restaurant to savor slow-cooked mtsvadi (grilled meat) and local wines while listening to stories from the hosts about the town's living traditions.
Leave Tbilisi early for a scenic drive to the Kakheti vineyards and begin with a guided cellar tour and tasting at Tsinandali Estate, where you can stroll the historic gardens and sample classic dry whites alongside estate-grown cheeses. Continue to nearby Shumi Winery for a hands-on qvevri demonstration and to taste amber wines aged in traditional clay vessels, finishing the morning with a light supra-style lunch of local cheeses, churchkhela and fresh bread at Pheasant's Tears' rustic courtyard while chatting with the winemaker about regional grape varieties.
After a relaxed estate lunch, drive through rolling vineyards to Ikalto Monastery to stroll its atmospheric ruins and learn about the medieval academy that shaped Georgian winemaking traditions, then continue to the nearby family-run Kindzmarauli Marani for a reserved tasting of semi-sweet Kindzmarauli wines paired with local honey and aged cheese. Finish the afternoon with a hands-on pottery workshop at Telavi Craft Studio, where you can shape your own wine cup (kantsi) and join a short informal tasting of local Kisi and Rkatsiteli at the studio while watching the low winter light gild the valley-perfect continuity from morning cellar tours into deeper regional history and craft.
As twilight falls over the vineyards, unwind with a farm-to-table tasting and dinner at Schuchmann Wines Chateau & Spa where you can sample reserved blends paired with seasonal stews while the chateau lights glow across the rows of vines. After dinner, join a cozy cellar-side folk-music session at Okro's Marani-sip a last glass of amber wine from a qvevri, listen to local songs, and stroll under the starlit Kakheti sky back to your guesthouse.
Start your final morning with a relaxed breakfast at Café Stamba before browsing the nearby stalls at the vibrant Flea Market at Dry Bridge for last-minute souvenirs like enamel Soviet kitsch and local enamel jewelry. Continue with a calming stroll through Rike Park, take the modern cable car to Sololaki Hill for one last panoramic view of the city, then pause at Pasanauri Bakery to pick up fresh khachapuri and churchkhela to enjoy later on your journey.
Stroll through the lively stalls of Dezerter Bazaar to pick up last-minute Georgian staples-dried fruits, churchkhela and locally smoked cheeses-then stop for a leisurely late lunch at Café Kala in the Sololaki quarter to savor a warm bowl of chikhirtma and a glass of local wine. Afterward, visit the intimate Museum of Georgian Folk Music and Musical Instruments for a quiet cultural pause before returning to your hotel to pack, allowing time for a final espresso at Sakhli #11 and a relaxed check of travel documents.
As the city winds down, take a slow culinary stroll through Vake Park's food stalls sampling seasonal pastries and hot soups from local vendors, then head to the elegant terrace of Funicular Restaurant for a final panoramic dinner where you can toast with a glass of Georgian wine while watching the city lights. Finish the night with a relaxed visit to Tbilisi Opera Square to enjoy the illuminated architecture and, if time allows, catch an informal late-night performance or a cozy coffee at the nearby Art-Café Home before returning to pack and rest for departure.