GEORGIA

Aug 21: Arrive in Tbilisi (The Capital)

Arrive in Tbilisi. Do not pick up your rental car yet; city traffic is highly congested and lane discipline is loose. Use the Bolt app (local Uber) for cheap, easy urban transport. Walk through Old Tbilisi’s cobblestone streets. Take the cable car up to Narikala Fortress for a view of the city. In the evening, head to the Abanotubani district and book a private room at a traditional sulfur bathhouse (like Chreli Abano) to shake off the jet lag. Follow it up with a heavy dinner of Khinkali (giant spiced soup dumplings) and Khachapuri (cheese bread).

Stay: Tbilisi Old Town.

Aug 22: Advanced Tbilisi & Local Wine Bars

Spend the day exploring the city’s complex history and modern edge. Check out the Dry Bridge Market—a massive, sprawling flea market where you can find vintage Soviet memorabilia, old cameras, and local art. Walk through the Fabrika district, a converted Soviet sewing factory that is now a hub for street art, cafes, and bars. In the evening dive into a "wine bar crawl" in the Sololaki neighborhood. Visit spots like Vino Underground or 8000 Vintages to taste traditional Qvevri amber wines (wines fermented in massive underground clay jars).

Stay: Tbilisi.

Aug 23: Ancient Capital to the Caucasus Mountains (Tbilisi to Kazbegi)

Driving Time: ~3 hours north on the Georgian Military Highway.

Pick up rental SUV from the city or airport and drive north. Your first stop is Mtskheta, the UNESCO-listed ancient capital, to see the stunning 11th-century Svetitskhoveli Cathedral. In the afternoon, continue up the dramatic Georgian Military Highway. Stop at Ananuri Fortress, a lakeside medieval castle, and the colorful Russia-Georgia Friendship Monument perched over a massive gorge near Gudauri. In the evening, arrive in Stepantsminda (Kazbegi), the mountain base town. Grab a drink on the terrace of the famous Rooms Hotel Kazbegi for an unobstructed view of Mount Kazbek (5,054m).

Stay: Stepantsminda.

Aug 24: High Peaks and Hidden Valleys

Driving Time: Minimal (~1 hour local driving).

In the morning, make the drive up the winding switchbacks to the iconic Gergeti Trinity Church. Sitting isolated at 2,170 meters with the mountain towering behind it, it’s one of the most famous views in the region. In the afternoon, drive out to the nearby Sno Valley and Juta village. Park your car and do the easy, stunning 1.5-hour walk toward the jagged Chaukhi Massif peaks. It feels like the Dolomites but with zero crowds.

Stay: Stepantsminda.

Aug 25: Soviet History & Cave Cities (Kazbegi to Central Georgia)

Driving Time: ~3.5 hours.

In the morning head back down the mountains and drive west toward Gori. This is the birthplace of Joseph Stalin. The Stalin Museum is an eerie, bizarrely preserved time capsule of Soviet-era propaganda, including his personal armored train car parked outside. In the afternoon, just 15 minutes outside Gori, explore Uplistsikhe, an ancient silk-road cave city carved directly into a rocky cliffside dating back to the Iron Age. In the evening, drive a short distance to the quiet, forested spa town of Borjomi. Taste the famous naturally carbonated salty mineral water straight from the spring at the mineral water park.

Stay: Borjomi or nearby Akhaltsikhe.

Aug 26: The Ultimate Fortress & Cliff Monastery (Borjomi to Vardzia)

Driving Time: ~2.5 hours.

In the morning, drive south through the rugged Mtkvari River gorge toward the Turkish border. Stop in Akhaltsikhe to explore the sprawling Rabati Fortress, a massive, beautifully restored complex blending Christian and Islamic architecture. In the afternoon, reach Vardzia, a jaw-dropping, 12th-century cave monastery complex carved into a multi-story cliff face containing hundreds of rooms, tunnels, and ancient churches. In the late afternoon, head west toward Kutaisi in the Imereti region.

Stay: Kutaisi.

Aug 27: Canyons & Caves of Western Georgia (Kutaisi to Imereti Wilderness)

Driving Time: ~2 hours local driving.

In the morning, visit the incredible Martvili Canyon or Okatse Canyon, where you can walk along suspended cliffside walkways or take a small boat through emerald waters beneath towering rock walls. In the afternoon, explore Prometheus Cave, a massive underground network featuring lit stalactites, underground lakes, and soaring caverns. Head back into central Kutaisi for dinner, trying regional Imeretian-style Khachapuri (stuffed with local melted cheese) and Imeretian wines.

Stay: Kutaisi.

Aug 28: Journey to Wine Country (Kutaisi to Kakheti)

Driving Time: ~4.5 hours (scenic transit across central Georgia into eastern wine country).

In the morning, depart Kutaisi and head east into Kakheti, the primary wine heartland of Georgia. In the late afternoon, arrive in Sighnaghi, a beautifully preserved 18th-century royal town built on a hilltop overlooking the massive Alazani Valley and the distant Caucasus mountains. Walk along the ancient defensive stone walls that still surround the town. In the evening, treat yourselves to a massive, traditional Supra (Georgian feast) paired with local micro-winery options at a spot like Pheasant's Tears or Lost Ridge Inn.

Stay: Sighnaghi.

Aug 29: Deep Wine Country, Final City Push & Flight Home

Driving Time: ~2.5 hours total driving.

• Morning: Drive north through the heart of Kakheti to Telavi. Stop by the vibrant local food market to see mountain cheeses, fresh spices, and rows of Churchkhela (walnuts dipped in grape juice and dried).

• Afternoon: Visit Tsinandali Palace (a stunning 19th-century noble estate with European-style gardens and a historic wine cellar) or do a final lunch and tasting at a local family-run vineyard.

• Late Afternoon / Evening: Drive back over the scenic Gombori Pass toward Tbilisi. Head into the city for a final relaxed dinner or coffee in Sololaki, pick up any last-minute souvenirs, and pack up.

• 8:30 PM – 9:00 PM: Drive to Tbilisi International Airport (TBS), return your rental SUV, check in, and board your 11:00 PM flight home.

My 8 Day Itinerary

8 Day Itinerary (Found on the Internet)

Phase 1: Capital & Caucasus Mountains

• Aug 21: Arrive in Tbilisi. Walk Old Town, Narikala Fortress, private sulfur bath session, dinner in Sololaki. (Stay: Tbilisi)

• Aug 22: Pick up rental SUV ->  Mtskheta (Svetitskhoveli Cathedral) ->  Georgian Military Highway -> Ananuri Fortress $\rightarrow$ Gudauri panorama -> $ Stepantsminda. (Stay: Stepantsminda / Kazbegi)

• Aug 23: Kazbegi switchbacks to Gergeti Trinity Church. Afternoon hike in Juta Valley or off-roading in Truso Valley. (Stay: Stepantsminda)

• Aug 24: Kazbegi ->  Gori (Stalin Museum) ->  Uplistsikhe Cave City ->  Borjomi mineral park. (Stay: Borjomi or Akhaltsikhe)

Phase 2: Caves, Canyons & Western Georgia

• Aug 25: Rabati Fortress -> Vardzia Cliff Monastery (explore multi-story cave complex) ->  Drive to Kutaisi. (Drive: ~4.5 hrs total. Stay: Kutaisi)

• Aug 26: Martvili Canyon (boat trip) or Okatse Canyon ->  Prometheus Cave. Evening in central Kutaisi. (Drive: ~2 hrs local. Stay: Kutaisi)

• Aug 27: Drive east across central Georgia to Kakheti Wine Country ->  Arrive in Sighnaghi. (Drive: ~5.5 hrs cross-country transit day. Stay: Sighnaghi)

Phase 3: Wine Heartland & Late-Night Airport Run

• Aug 28: Full day in Sighnaghi & Alazani Valley – Wineries (Pheasant's Tears), ancient defense walls, traditional Supra feast. (Stay: Sighnaghi)

• Aug 29 (Final Day & Airport Night):

  • Morning: Drive back toward Tbilisi via the scenic Gombori Pass. Stop at Tsinandali Estate or Telavi local market along the way.

  • Afternoon: Arrive in Tbilisi. Browse Dry Bridge Flea Market for vintage Soviet gear/souvenirs, grab coffee at Fabrika, or relax at a café.

  • Evening: Have a long, final dinner in Sololaki, pick up Churchkhela (grape/walnut candies), pack up bags.

  • 12:00 AM Midnight (Technically early Aug 30): Drive 20–25 minutes to Tbilisi International Airport (TBS), drop off your rental SUV, check in, and board your 3:10 AM flight.