In Baku’s Old Town, cobblestones wind beneath the Maiden Tower, while the modern Heydar Aliyev Center — a Zaha Hadid masterpiece — curves dramatically. This juxtaposition of ancient and contemporary is Baku’s unique charm.

At Martyr’s Lane, a park and memorial to those who fought for independence, views of the city and the Bay of Baku await. The Old Town, a UNESCO World Heritage Site, invites further exploration. Wander along cobbled alleyways, pausing at Shirvan Shah’s Palace, the last residence of the Shirvan rulers, before viewing the iconic Maiden Tower and the Heydar Aliyev Center.

The road winds westward through the foothills of the Caucasus Mountains, leading to Shamakhi. Here stands the Juma Mosque, built on the site of an ancient Zoroastrian temple. At the Savalan Winery, enjoy lunch and a wine tasting with stunning views. Arriving in Sheki, a local dinner offers a first taste of the historic town.

A lesser-known star of the Silk Road, Sheki sits nestled in the foothills of the Greater Caucasus, its silk once traded as far as Japan. Today, see the surviving caravanserais and UNESCO-protected Sheki Khan’s Palace, with its rose gardens and vibrant Persian carpets. The town’s stained-glass Shebeke windows, handcrafted by skilled artisans, adorn palaces and hotels. Witness their artistry in progress at a local Shebeke studio. The nearby village of Kish adds to the allure.

Beyond the border lies the road to Tsinandali. Gremi, a former royal citadel in Kakheti, offers a glimpse into the past of a once-flourishing town through its citadel and the Church of the Archangels. Following a culinary masterclass at a Shilda winery, discover the summer home, garden and winery of Tsinandali's Family Estate, former residence of poet Alexander Chavchavadze.

The Kakheti Region, known for its winemaking traditions, invites you to weave your way through its picturesque landscapes. The Bodbe Nunnery reveals the final resting place of St. Nino, female Evangelist of Georgians. In Sighnaghi, a fortified town perched on a hillside, stunning views unfold. Wander the town's narrow streets, learning about its rich wine and carpet-making history. After a local lunch at a welcoming family home, continue to Tbilisi.

A blend of cultures, much like its cuisine, Tbilisi reflects Central Asian, Russian and Turkish influences. Best explored on foot, the Old Town is a winding mix of street bazaars, faded wooden balconies and diverse architectural styles. Alongside your private guide, see historic landmarks like the Sulphur Baths; Georgian Synagogue, a Jewish prayer house; Sioni Cathedral; and Anchiskhati Basilica, which coexist with contemporary galleries and shops.

Perched atop a cliff near Mtskheta, cruciform-shaped Jvari Monastery — a UNESCO World Heritage Site — overlooks the Aragvi and Mtkvari Rivers. Descend into the valley to Svetitskhoveli, its cathedral where Christ’s robe is said to be buried. The winding Georgian Military Highway leads to the medieval Ananuri Fortress Complex, former home of the Dukes of Aragvi. Arrive in the village of Kazbegi, nestled amidst dramatic mountain peaks.

Rising high above Kazbegi, Mount Kazbek — swirled in ice and legend — is the site where Prometheus was chained. Perched on its flank, 7,100 feet up, Gergeti Trinity Church offers a breathtaking view and a glimpse into the region’s dramatic history. Hike or drive up to reach it before visiting a local felt studio and sitting down to lunch with a local family.

Return to Tbilisi, stopping at Château Mukhrani for lunch paired with local wine. In rock-hewn Uplistsikhe, explore echoing halls, ancient wine presses carved in stone, meandering streets and the remains of Georgia’s oldest theater, carved into the rocky plateau.

Tbilisi is yours to explore alongside your guide, starting with a stroll along Rustaveli Avenue and the collection at the Georgian Museum of Fine Arts or the Tbilisi History Museum. Your walking tour continues through the Sololaki district on the slopes of Mount Mtatsminda.

Cross the Georgia-Armenia border by road, continuing toward Yerevan with a stop at medieval Haghpat Monastery, a UNESCO World Heritage Site. In the mountainous spa town of Dilijan Old Sharambeyan Arts and Crafts Street is ideal for a stroll, a cup of coffee in hand. You’re then invited to the home of a Russian Molokanskaya family for tea and homemade pastries. For a scenic break en route to Yerevan, Lake Sevan is perched along the banks of the Hrazdan River.