Arrival in Skopje. Lunch. Transfer to the hotel and accommodation. Walking tour of Skopje (app. 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 Theresa, the old Turkish market, St.Spas church where you can witness one of the most beautiful wood-carved iconostases on the Balkans peninsula, created by Debar masters in 19th century. 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. 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.

After breakfast, tour of the winery complex and wine tasting. Departure for Bulgaria. On the way an optional hiking tour to Koleshino waterfalls near town of Strumitsa. Lunch. Crossing the North Macedoinan-Bulgarian border. Arrival in the town of Melnik - the smallest town in Bulgaria, famous for it 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. Drive to the village of Brestovitsa, famous for its wines. Visit to the boutique wine cellar Todoroff and wine tasting. Drive to Plovdiv. Dinner. Accommodation 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. And the best Roman heritage – Roman theatre, Roman stadium. Departure for Starosel. Visit to Starosel and walk around the latest excavations of the Thracian tombs at Starosel. 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. Dinner. Overnight in Sofia.

Breakfast. Guided sightseeing tour of Sofia, including visits to St. Alexander Nevski Cathedral, Rotunda St. George and St. Sophia Church. Visit of wine museum in Sofia. Optional visit of Boyana Church and the National History Museum in the afternoon. Dinner. Overnight in Sofia.

Breakfast. Transfer to the airport and departure from Sofia/Skopje.