Fly from Jaipur International Airport to Tbilisi International Airport on your booked one-stop itinerary. For an international departure, arrive at Jaipur Airport around three hours early; keep passports, onward tickets, hotel details, and travel insurance accessible for check-in and transit formalities. The full journey will likely take most of the day, so plan the evening gently rather than adding sightseeing before check-in.
After landing, use the official airport taxi desk or a pre-booked transfer to your Old Town hotel. The drive into central Tbilisi usually takes 30–45 minutes, though evening traffic can stretch this longer. A metered taxi or app-based ride is preferable to negotiating with unsolicited drivers. Check in, freshen up, and take a short rest before heading out; December evenings are cold, so bring a warm layer and shoes suitable for uneven cobblestones.
Begin at Rike Park, where the riverside paths give you an easy first look at the city without a demanding walk. Cross the Bridge of Peace after dark—its illuminated glass-and-steel canopy is especially photogenic, with views toward the Mtkvari River and the old hillside. Allow roughly 30 minutes at the bridge and another 45 minutes for a relaxed circuit of the park. From the park, walk across toward the Kala district; the route is straightforward, but expect some steps and polished, slippery paving in damp weather.
Continue through Shardeni Street and its neighboring lanes, browsing small galleries, wine bars, and atmospheric courtyards. It is tourist-oriented, but pleasant for a first-night wander; keep bags close in busy stretches. Finish with dinner at Keto and Kote in Sololaki, a short taxi ride or uphill walk from the Old Town. Reserve ahead if possible, particularly for a group of five, and budget about 50–90 GEL per person excluding wine. Share dishes such as khachapuri, khinkali, and seasonal Georgian salads, and ask the restaurant to pace the meal—you will want an early night after the flight.
Start early in Old Tbilisi, ideally around 09:00, when the lanes are quieter and the winter light is best for views. Walk or take a short taxi to the lower station of the Narikala Fortress cable car, then ride up if operating; otherwise, use the steep footpaths from the Abanotubani side. Allow about 1½ hours for the fortress walls and viewpoints, wearing shoes with good grip because the stones can be slippery. From here, continue along the ridge to Mother of Georgia, a roughly 15–20-minute uphill walk; spend about 30 minutes enjoying the panorama over the Mtkvari River and photographing the statue. The cable car usually operates from late morning into the evening, but winter schedules and weather can change, so check locally before relying on it. A taxi between points should generally cost around 5–10 GEL.
Descend into the Abanotubani sulfur-bath district for an hour of wandering among the brick-domed bathhouses, tiled facades, and narrow lanes. You do not need to book a bath for this visit, but if the group wants a private room later, reserve directly with a bathhouse rather than accepting unsolicited offers in the street. Walk onward through Kala to Café Leila, an atmospheric vegetarian restaurant with ornate interiors and a relaxed pace; budget approximately 30–55 GEL per person. Try Georgian dishes such as lobio, ajapsandali, or khachapuri, and allow extra time if the café is busy. The walk from the baths takes about 10 minutes, mostly through pedestrian-friendly historic streets.
After lunch, take a taxi or walk approximately 20 minutes toward Rustaveli Avenue for the Georgian National Museum. Plan about 1½ hours inside; the archaeological and historical collections are the highlight, and indoor time is welcome in December. Check the current opening day and hours before setting out, as museums commonly close one day each week; admission is usually modest, around 10–20 GEL depending on the exhibitions. Finish with an easy early-evening stroll along Rustaveli Avenue, passing the theaters, bookshops, and grand civic buildings as the avenue lights come on. For the return to your accommodation, use Bolt, widely available in Tbilisi, rather than hailing a taxi; keep the evening unhurried, since the cobbled Old Tbilisi lanes are more enjoyable at walking pace.
Leave Tbilisi around 08:00 in your pre-booked private 4WD or van, allowing roughly 3.5–5 hours to reach Stepantsminda with winter stops. Ask the driver to confirm the road status the previous evening, as snow or ice can affect timings. The first photo stop is Zhinvali Reservoir, where the deep blue water and wooded Caucasus slopes look especially striking in the clear morning light; allow about 20 minutes. Continue to Ananuri Fortress, roughly 15–20 minutes farther along the highway. Spend around an hour exploring its stone walls and lakeside churches, but wear shoes with good grip—the paths can be wet or icy in December. Keep a few small GEL notes for roadside toilets and snacks.
Continue north toward Gudauri, stopping at the Russia–Georgia Friendship Monument for about 30 minutes. The panoramic balcony can be very windy and slippery, so bring gloves and avoid lingering near icy edges. From here, the drive to Stepantsminda usually takes another 1–1.5 hours, depending on snow and traffic. Once checked in or after leaving your bags, warm up at Rooms Hotel Kazbegi in its lounge, an easy first stop in town with excellent mountain views. Order tea, hot chocolate, or a drink—budget approximately 25–60 GEL per person—and allow about an hour to relax rather than rushing straight back outdoors.
If the weather and road conditions are safe, arrange a local 4WD taxi from Stepantsminda up to Gergeti Trinity Church; do not attempt the snowy track on foot in fading light. The return trip and viewpoint visit take around 1.5 hours, and sunset is beautiful when the clouds stay clear, but treat this as weather-dependent—your driver should confirm access before departure. Back in Stepantsminda, have dinner at Khevi Restaurant for Georgian comfort food such as khinkali, lobio, and grilled meats; allow roughly 35–60 GEL per person, including shared dishes. December evenings are extremely cold, so carry layers, charge your phones before the church visit, and keep the evening flexible in case the mountain road closes.
Leave Stepantsminda around 09:00 in your pre-booked private van or 4WD, allowing roughly 3.5–4.5 hours to reach Tbilisi. Check the Georgian Military Highway forecast before setting off; winter ice or snow can easily add time. Ask your driver to drop luggage at your accommodation and continue straight to the Chronicle of Georgia, rather than going into the centre first. The monument is outdoors, free to visit, and usually best in daylight; allow about an hour for the huge carved panels and the broad views over Tbilisi Sea. Wear sturdy shoes, as the paved approach can be slippery.
From Chronicle of Georgia, take a taxi—about 25–35 minutes depending on traffic—to Fabrika Tbilisi in Chugureti. Its leafy courtyard, independent design shops and cafés make a good relaxed stop after the long drive; plan around 1–1.5 hours. Then take a short taxi or roughly 15-minute walk toward Dezerter Bazaar near Station Square. Browse the cheese, spice, dried-fruit and churchkhela stalls, but go before about 18:00, when many vendors begin packing up. Prices are negotiable, though it is polite to ask before photographing people or stalls.
Head back toward Dedaena Park for Dry Bridge Market, around 10–15 minutes by taxi from the bazaar. In December, some sellers may close early or skip the market in poor weather, so treat this as a flexible 45-minute stop; look for Soviet-era objects, enamelware, paintings and handmade crafts rather than expecting fixed prices. Finish at Puri Guliani in Chugureti, where a taxi from Dedaena Park takes about 10 minutes. Book ahead for five people if possible and budget approximately 35–70 GEL per person for Georgian breads and contemporary local dishes; confirm the evening kitchen hours on the day, as winter schedules can change. Keep the rest of the night easy after the mountain drive—your accommodation is best reached by taxi rather than relying on a late walk with luggage.
Leave Tbilisi around 08:30 with your pre-booked driver, taking the Kakheti Highway toward Sighnaghi. The drive usually takes 2–2.5 hours; ask the driver to keep your luggage locked in the vehicle while you explore. Stop first at Bodbe Monastery of St. Nino, just outside town, for about an hour. The monastery grounds are peaceful in winter, with wide views across the Alazani Valley, although fog can sometimes obscure the mountains. Dress modestly—shoulders and knees covered—and wear shoes with grip, as the paths can be damp or slippery.
From Bodbe Monastery, it is a short drive into Sighnaghi. Spend roughly 1.5 hours wandering the compact old town, looking out for the painted balconies, cobbled lanes, and sections of the defensive wall. The wall walkway can be windy in December, so a warm layer is useful; some stairways and viewpoints may be uneven. Continue to Pheasant’s Tears for lunch and a relaxed natural-wine tasting, allowing about two hours. Its Georgian dishes and seasonal menu pair well with Kakhetian wines; budget approximately 60–120 GEL per person depending on the tasting. Reserve ahead for five people, particularly if you want a full tasting rather than lunch only.
After lunch, walk through the central lanes to Sighnaghi Museum, usually a 5–10-minute stroll depending on where you finish. Allow around 45 minutes for its regional archaeological and ethnographic displays; check the opening time locally because winter hours can be shorter than in summer. Meet your driver around 17:00 for the return to Tbilisi, allowing another 2–2.5 hours via the Kakheti Highway. Keep some water and snacks in the car, and confirm the exact pickup point in advance—parking in the old town can be limited. Five passengers sharing a 150–250 GEL vehicle makes this much easier and more comfortable than coordinating separate marshrutkas.
Return from Sighnaghi to central Tbilisi by your pre-booked private car, allowing around 2–2.5 hours; for a flight day, arrange an early departure rather than relying on a shared marshrutka. Leave your bags at the hotel or in the driver’s locked vehicle and head straight to the Tbilisi Flea Market at Dry Bridge, beside Dedaena Park. The market is best in the morning, when sellers are setting out Soviet-era objects, handmade crafts, old postcards, and small souvenirs; allow about an hour and carry cash in Georgian lari, as card payments are uncommon. Prices are negotiable, but be polite and check fragile items carefully before buying.
Take another 45 minutes for a relaxed riverside walk through Dedaena Park, on the left bank of the Mtkvari River. December can be cold and the park is open-air, so keep this flexible if the paths are wet; it is a pleasant final pause rather than a major sightseeing stop. From here, a short taxi ride or roughly 15–20-minute walk brings you toward Freedom Square for lunch at Machakhela, a convenient, budget-friendly choice for Adjarian and Georgian comfort food. Allow about an hour and expect approximately 25–50 GEL per person; khachapuri, lobio, khinkali, and salads are easy dishes to share among five people.
After lunch, collect your luggage and leave central Tbilisi for Tbilisi International Airport around three hours before your flight. In normal traffic, the taxi ride takes 30–45 minutes, but allow extra time for congestion and winter weather; your hotel can arrange a larger vehicle if you have several suitcases. At the airport, complete check-in and baggage drop first, then confirm that bags are tagged through to Jaipur and check the connection requirements for your one-stop route. Keep passports, boarding passes, and essential medicines in hand luggage, and leave time for security and a little duty-free shopping before beginning the return journey.