Depart Sofia in the morning for a full-day excursion to Plovdiv, the second-largest city in Bulgaria and one of the oldest towns in the world. Learn about the history of Plovdiv, dating back to Troya and Mycenae. During a 2 hour guided tour in the old town, discover the history and the culture of the 7,000-year-old settlement from its Roman, Byzantine, and Ottoman periods to the present day. Admire museums, churches, historic monuments, revival period houses, souvenir shops, and cobblestone streets. See the Ethnographic Museum and the well-preserved ruins of the ancient Roman Theater. After the guided tour, you will have about 2 hours of free time for lunch and shopping. The, relax on the journey back to Sofia.

Leave Sofia and enjoy a full-day tour to Plovdiv, Asen's fortress, and Bachkovo Monastery with a licensed guide. See some of the most interesting historic sites in the area, like Nebet Tepe, the Roman theater of Phillippolis, and the Church of the Holy Mother of God on this tour. Leave Sofia and set out for a full-day tour to Plovdiv, Asen's Fortress, and Bachkovo Monastery. Start the day with hotel pickup in Sofia and relax on the 90-minute drive to Plovdiv. Visit the site of Nebet Tepe, an ancient settlement founded around 4000 BC, and see some historical buildings. Travel to the Roman theater of Phillippolis, one of the world's best-preserved ancient theaters. Marvel at the intricate wooden architecture of Hindliyan's house before moving on to the modern Kapana district to explore the shops and wander one of the longest pedestrian streets in Europe. Relax on the approximately 30-minute drive from Plovdiv to Asen's Fortress, perched on top of a hill in the beautiful Rhodope Mountains. Learn how the fortress that defended the route from the Aegean Sea to Thrace, and see the ruins of the fort itself and the Church of the Holy Mother of God. Admire some of the fragments of fourteenth-century murals in the church, and see its rectangular tower, believed the be the earliest preserved tower of its kind in the Balkans—Marvel at breathtaking views from the top of the fortress before departing for the next stop. Leave the fortress behind and stop at Bachkovo Monastery, the second-largest monastery in Bulgaria. Explore the main church with one of the oldest iconostasis in Bulgaria and the miraculous Icon of the Virgin Mary, the biggest fresco from the nineteenth century. Wander the Monastery and see the old dining room and original marble table, where monks ate for over three centuries, and gazer at the well-preserved murals in the St. Archangels and St. Nicolas churches. Sit in the courtyard and enjoy the peaceful atmosphere and impressive trees. Buy handicrafts, honey, homemade jam, yogurt, herbs, and other gifts on the walk back by the monastery alley before returning back to Sofia on an approximately 2 hour and 20-minute drive.

After a 2-hour drive, begin this full-day tour in one of Europe's oldest towns, Plovdiv. Walk along cobblestone streets and visit a 19th-century house to learn about the local production of alcoholic drinks and rose oil products. Explore the Roman Theater, Roman Stadium and church with virtual reality glasses before enjoying 2 hours of free time to walk around and have lunch and coffee along the main pedestrian street. After exploring Plovdiv, meet your van and guide to make the 30-minute drive to Asen's Fortress. Admire this beautiful, medieval structure and learn about the history of the place before taking photos from the top. Start your journey back to Sofia with an expected arrival time of approximately 6:00 PM.

Rila Monastery, at an elevation of 1,147 meters, is situated along the Rilska River in the highest mountains of the Balkan Peninsula. Founded in the 10th century by the hermit St. Ivan Rilski, it is today Bulgaria’s most famous site. Known also as the Holy Rila Retreat, it is considered to be the most outstanding monument of the Bulgarian National Revival period, and the ultimate expression of the Bulgarian genius in matters of spirit, culture, architecture, construction, icon painting, and woodcarving. The monastery, as it now stands, was built in the period 1816-1847. The first stop at the monastery is the main church, the Nativity of the Virgin, elaborately decorated with murals both inside and outside. The church houses the holy relics of St. Ivan Rilski as well as the tomb of Boris III, the last Bulgarian king. Next to the main temple is the only structure that remains from the 14th century: the Tower of Hrelyu. This strong fortification was erected by the local feudal lord Hrelyu in 1334. The Transfiguration Chapel on the top floor features precious murals from the 14th century. In the monastery museum you’ll see the impressive wooden cross carved by the monk Rafail. This unique piece of art contains 36 scenes from the Bible and about 600 figures as small as a grain of rice. Before visiting the monastery you have the option of enjoying lunch at a restaurant perched above the Rilska River to try the local speciality; grilled or fried trout.