Two Countries, One Journey: Istanbul to Tbilisi
From the Bosphorus to the Caucasus, overland across the border that joins Türkiye and Georgia.
Highlights
Signature moments
Ani, city of a thousand churches
A ruined medieval capital on the closed border, best at sunset.
Tbilisi old town
Sulphur baths, carved balconies and a very long dinner.
Kazbegi & Gergeti
The church under the mountain, and the road that gets you there.
Itinerary
Day by day
- 01
Istanbul: the old city
Hagia Sophia, the bazaar and a first evening on the water.
Meals: Breakfast Boutique hotel in Istanbul - 02
Istanbul: Bosphorus & Beyoğlu
A boat up the strait, then the back streets of Beyoğlu.
Meals: Breakfast Boutique hotel in Istanbul - 03
Fly to Kars
East to the borderlands, and Ani in the late light.
Meals: Breakfast Boutique hotel in Kars - 04
Kars to Tbilisi
Overland across the frontier, arriving in Georgia by evening.
Meals: Breakfast Boutique hotel in Tbilisi - 05
Tbilisi old town
Sulphur baths, the fortress and a supra that runs long.
Meals: Breakfast Boutique hotel in Tbilisi - 06
Mtskheta & a wine cellar
The old capital, then a family winery in the hills.
Meals: Breakfast Boutique hotel in Tbilisi - 07
Kazbegi & Gergeti Trinity
The Georgian Military Highway and the church under the peak.
Meals: Breakfast Mountain hotel in Kazbegi - 08
Kakheti wine country
Eight thousand years of winemaking, tasted properly.
Meals: Breakfast Winery hotel in Kakheti - 09
Sighnaghi & David Gareja
Hill town walls, then a cave monastery in the steppe.
Meals: Breakfast Winery hotel in Kakheti - 10
Departure from Tbilisi
Return to the capital for departure.
Meals: Breakfast
What's included
Private guiding and transfers Accommodation as listed Breakfast daily Entrance fees to sites named in the itinerary
Optional upgrades
Domestic flights Additional nights Private cooking classes Upgraded room categories
Staying
Boutique hotels, riads and family-run guesthouses
Made for
Couples, families and private groups who prefer their own pace
Trusted
What travellers and partners say
The most relaxed two weeks of my life. Someone had always thought of the small thing — the cold water, the right song on the drive, the table by the window.
They rebuilt half our honeymoon when a flight changed overnight — without a single grumpy message. Felt like travelling with friends who happen to be superhuman.
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