Arrival in Skopje. Lunch. Transfer to the hotel and accommodation. Walking tour of Skopje (approx. 2 hours): Macedonia Square with the sculptural compositions from the project "Skopje 2014", among which the monument of Alexander the Great and the Arch of Triumph "Macedonia", Memorial house of Mother Teresa, the old Turkish market. Dinner. Overnight in Skopje.

Breakfast. Departure for Tikvesh Wine Region. Drive to Stobi and tour of the archaeological reserve – one of the most developed Roman cities in the Roman province of Macedonia, early Christian center. Wine tasting in the local winery and lunch. Then visit of the famous Tikvesh Winery in the town of Kavadartsi. Tikvesh is the center of the North Macedonian wine production which has been cultivated for more than 120 years. Accommodation at Popova Kula Wine Estate. Dinner. Overnight in Popova kula.

Breakfast. Tour of the winery complex and wine tasting. Departure for Bulgaria. On the way - lunch at a local restaurant and short hiking tour to Koleshino waterfalls near the town of Strumitsa. Crossing the North Macedoinan-Bulgarian border. Arrival in the town of Melnik - the smallest town in Bulgaria, famous for its excellent wines and sand-stone pyramids. Sightseeing tour of Melnik including a visit to Kordopulova Museum house and wine tasting. Dinner. Overnight in Sandanski.

Breakfast. Departure for Rila Monastery. Sightseeing tour of the monastery, included in the list of UNESCO. Lunch at a local restaurant in the valley of Rilska river. Drive to the village of Brestovitsa, famous for its wines. Visit to the boutique wine cellar Todoroff and wine tasting. Drive to Plovdiv. Accommodation, dinner and overnight in Plovdiv.

Breakfast. Sightseeing tour in the Old town of Plovdiv – European capital of culture 2019. Brilliant examples of the Bulgarian national revival period are preserved here along with the heritage of the largest Roman city on the territory of present-day Bulgaria – Roman theatre, Roman stadium, ancient forum and odeon, early Christian basilicas and a synagogue. Lunch at a local restaurant. Departure for Starosel. Sightseeing tour of the local Thracian tomb. The village is known for its abundance of ancient Thracian sites, with finds dating back to the 5-6 millennium BC. Wine-tasting at Starosel winery. Departure for Sofia. Accommodation and dinner. Overnight in Sofia.

Breakfast. Guided sightseeing tour of Sofia, including visits to St. Alexander Nevski Cathedral, St. Sophia Church and the Rotunda of St. George. Wine tasting at a local winery and lunch at a local restaurant. In the afternoon - free time for visiting museums and shopping, or optional tour to Boyana Church and the National History Museum. Boyana Church is included in the world cultural heritage list of UNESCO because of the wonderfully preserved frescos from the 13th century. National History Museum houses huge collections of artifacts representing the rich history of Bulgarian lands including some of the most famous treasures of the ancient Thracian rulers. Dinner. Overnight in Sofia.

Breakfast. Transfer to Sofia airport and departure.