Arrive in Tbilisi and transfer to our hotel.  Marriott Tbilisi (D)

Enjoy a walking tour of Old Tbilisi to soak up the multiethnic atmosphere of this important link between East and West including a stop at the city’s oldest church, Anchiskhati Basilica. Explore the Abantobuani Historic District where the famous sulfur baths are located, and take a funicular ride up the slopes of Mt. Mtatsminda to the ancient Narikala Fortress. Stop in at a gallery to visit a local artist. Experience an evening Georgian Table or supra – a uniquely Georgian dining experience accompanied by intriguing polyphonic singing and Georgian wines. Marriott Tbilisi (B,L,D)

Continue our exploration of Tbilisi with a stroll along Rustaveli Avenue, Tbilisi’s main thoroughfare, to the Simon Janashia Museum of Georgia, a component of Georgia’s National Museum for a look at some of the country’s most significant archaeological finds. Upstairs, spend time in the Museum of Soviet Occupation to learn more about the country’s history as a Soviet Socialist Republic. After an independent lunch, we continue to learn more about Tbilisi’s Soviet past with a drive through the city and into the outskirts to see examples of Soviet-era architecture. Then stop at the Chronicle of Georgia Monument, often referred to as the “Georgian Stonehenge.” This dramatic complex depicts figures from Georgian history, including the kings and queens who laid the foundation for the country. This evening, have an opportunity to meet a local Georgian guest over cocktails. 
Marriott Tbilisi (B)

Venture east to the wine region of Kakheti to enjoy an in-depth vineyard and winery tour with tasting at one of the country’s most famous and successful natural wineries. Learn all about qvevri wine-making – an ancient Georgian winemaking technique involving clay jugs buried in the ground. Head toward Tsinandali and our fabulous hotel for the next two nights, stopping en route to explore the charming hilltop town of Signagi, and the Bodbe Monastery nearby. Radisson Tsinandali Estate Hotel (B,L)

Visit the family estate (now a museum) of Alexander Chavchavadze, a 19th-century Georgian aristocrat and poet. Here he and his father founded the first and foremost winery in the country, which still produces the dry white Tsinandali wine. Lunch at the home restaurant of one of Georgia’s rising star female chefs in a nearby village. Stop in Telavi, a town of some 20,000,  and the administrative and cultural center of Georgia’s wine-growing region, Kakheti. The town has been in existence from at least the 1st century, when it was a stop on one of the trade routes from the Middle East to Europe. Telavi is home to the only well-preserved palace in Georgia, the 17th-century castle of Herekle II. In an interesting sidelight, Telavi is the sister city of Napa Valley. Also visit the Mzemoe workshop where they produce high-quality Tushetian rugs; traditional knitted slippers (chities); and felted, knitted, and embroidered accessories inspired by traditional ornaments and designs.
Radisson Tsinandali Estate Hotel (B,L)

Make our way along the picturesque driving route known as the Georgian Military Highway through rolling green hills and steep arid mountains dotted with ancient stone defensive towers, then over the Krestovy Pass at almost 8,000 feet. Along the way, stop for photos at the Russia-Georgia Friendship Monument and for views of herds of sheep and old fortresslike churches watching over the villages. Enjoy two nights at a mountain retreat in the town of Kazbegi, a small alpine village set in a monumental bowl of mountain peaks, including one of the Caucasus’ highest, Mt. Kazbek. Rooms Hotel Kazbegi (B,L,D)

Explore Trinity church perched on a hill above the town (hiking option available) and then visit villages in the area for lunch with a private family, including a khinkali (Georgian dumpling) making lesson; and a meeting with a local priest at the Dariali Monastery at the Georgian frontier. Rooms Hotel Kazbegi (B,L)

Today we make our way back to Tbilisi stopping at the feudal stronghold of Ananuri, UNESCO-listed Mtskheta, Georgia’s ancient capital, and the Jvari Monastery, situated at the confluence of the Kura and Aragvi Rivers. Toast our journey at a farewell feast of traditional Georgian favorites this evening. Marriott Tbilisi (B,L,D)

Depart Tbilisi for Yerevan, or for flights home to the U.S. (B, flight time permitting)