Sofia’s center affords the unique opportunity to walk down a real “yellow brick road,” paved in 1907 with Austrо-Hungarian cobblestone. Important landmarks include the imposing Alexander Nevski Cathedral, the Russian Church, the Sofia Synagogue, the National Theater and city garden, parliament, the Royal Palace, the fourth-century Roman Rotunda and newly excavated Roman ruins, and the 1950s socialist administrative complex. Along our walking tour, we’ll be making stops to sample traditional Bulgarian dishes, street food, the iconic boza beverage, banitsa, lyutenitsa, and more. We’ll also have a specialized wine-tasting event featuring the best wineries of the Black Sea region. After free time in the afternoon, we’ll end the day with a festive gourmet wine-and-dine event. Overnight in Sofia. Grand Hotel Sofia 5*.

• Breakfast
• Grand Hotel Sofia

Today we head east through the picturesque and fertile Thracian Valley. The region is home to a few of the country’s leading wineries, subdivided into two distinct microregions – western and eastern Thrace. Along our way, we’ll stop for wine tasting visits at two renowned regional wineries. Southcentral Bulgaria is also the historic locale of the settlements of the ancient Thracians, with multiple burial tombs. You will learn about the rich Thracian culture and rituals, as well as about the Thracians’ ancient winemaking practices and worship of Dionysus (Zagreus), the god of wine. Our final destination for the day is the south Sakar area, which over the past decade has become home to several top-notch boutique wineries. One of them is Bratanov Family Vineyards, whose 3-Blend Cabernet Franc & Merlot & Rubin 2018 was awarded the 2023 DiVino wine-of-the-year award, the most prestigious Bulgarian recognition. Another of Sakar’s wineries, Zaara Estate, offers luxury accommodations. Zaara is also known for its organic dairy farm, whose specialty cheeses we’ll taste together with their wines. Overnight in Zaara Estate.

• Breakfast
• Zaara Estate

After we complete our tour of the Sakar wineries located in and around Harmanli, we will head toward the Plovdiv region. South of the city lies one of Bulgaria’s most fascinating spiritual sites, the 11th-century Bachkovo Monastery, nestled in the scenic Rhodope Mountains. We will have a presentation of traditional Bulgarian spices and herbs, including the iconic chubritsa (a mixture of dried winter savory, fenugreek, summer savory, and paprika). You will be able to purchase organic spices and herbs, produces at a local family farm. We will then continue to the medieval Assenovo Fortress and church, which afford breathtaking views of the narrow canyon along the Chaya River. The vineyards around Assenovgrad are considered the birthplace of Mavrud, Bulgaria’s best-known indigenous red varietal. Late afternoon arrival in beautiful Plovdiv, Bulgaria’s second-largest city. Overnight in Plovdiv. Hotel Residence City Garden 5*.

• Breakfast
• Hotel Residence City Garden

Europe’s oldest city combines layers of its Thracian, Roman, Byzantine, Ottoman, and Bulgarian Revival past. As we walk the cobbled streets of the Old Town, we’ll admire impressive examples of opulent nineteenth century vernacular architecture, a second-century Roman theater and stadium, and a 14th century mosque. Plovdiv’s promenade has lovely cafes and restaurants and is a popular destination for afternoon and evening walks. The city is also home to a spectacular Roman archaeological complex – the newly excavated 4th-century CE Bishop’s Basilica. A short drive to the nearby village of Brestnik will take us to the stunning Dragomir Winery Estate, whose wines are among the country’s best. We will dine at a renowned Plovdiv restaurant, located in the bustling Kapana neighborhood. And we’ll have a specialized wine-tasting event in Cork&Fork, the city’s newest wine spot. Overnight in Plovdiv. Hotel Residence City Garden 5*.

• Breakfast
• Hotel Residence City Garden 5*

Our drive today will take us through gorgeous parts of the mountainous southwest. After we complete our exploration of the Thracian wine region, we will ascend the slopes of the picturesque Rhodope Mountains. The Bansko region is home to a group of villages known for their unique regional cuisine and folklore. We will visit the Dobarsko village, cuddled in the southwestern slopes of the Rila mountain. The small local church is not to be missed. One of its murals is particularly famous worldwide, as it seems to depict Jesus in a spaceship. We will have a rustic homemade meal and a cooking demonstration of traditional regional recipes. We then continue to the charming mountain town of Bansko. As we stroll through its cobblestoned streets and enjoy the historic fortified stone palaces and the gorgeous Holy Trinity Church, you will get a tangible sense of what life felt like in the 18th and 19th century. During the winter, Bansko is also the hub of one of Bulgaria’s top ski resorts. We’ll end the day in the Melnik outskirts and check into the spectacular Zornitza Family Estate Relais & Châteaux.

• Breakfast
• Zornitza Family Estate Relais & Châteaux

The Melnik wine region is home to several of Bulgaria’s preeminent wineries. We will sample their wines amid bucolic scenery – rolling vineyard hills amid majestic mountains. The indigenous Broadleaf Melnik red variety is Bulgaria’s other iconic native wine, alongside Mavrud. While visiting the Zlaten Rozhen winery, we will also stop by Bulgaria’s best Antique Auto Museum, displaying rare vintage models from both the West and the Soviet Bloc. We will also explore the historic town of Melnik and learn about its vernacular architecture, surrounding stone pyramids, and the town’s centuries-old winemaking tradition. The area south of Melnik is home to a unique regional cuisine, and we will enjoy signature rural dishes. Overnight in Zornitza Family Estate Relais & Châteaux.

• Breakfast
• Zornitza Family Estate Relais & Châteaux

Our morning drive will take us through the Kresna Gorge, passing by the southwestern towns of Sandanski and Blagoevgrad, home to the only American university in the region. Our main destination today is the Rila Monastery, the nation’s greatest religious symbol and a UNESCO site. Perched in the heart of Bulgaria’s tallest mountain, the monastery was founded in the 10th century and has been an influential spiritual and cultural hub over the centuries. Bulgaria’s King Boris III was buried here in 1943. Back in Sofia, you’ll have free time in the afternoon to explore parts of the capital you did not get to see or to get a few lastminute gifts for friends back home. We’ll end the day with a delicious farewell dinner. Grand Hotel Sofia 5*.

• Breakfast, dinner
• Grand Hotel Sofia 5*

Free time and departure.

• Breakfast