Rila Monastery - The first and primary stop on the tour. It is the largest and most significant Orthodox monastery in the country. The monastery was established between 927 and 941 by St. John of Rila the Wonderworker (or possibly by his disciples, according to some sources) on the site of an old post house in the Rila Mountains. In 1335, a local feudal lord named Protosevast Hreljo built a defense tower and a small one-nave church in the courtyard of the current monastery. The tower is the oldest surviving structure in the monastery complex and features the “Holy Transfiguration” chapel at its top, adorned with valuable frescoes from the 1430s. On September 21, 1378, King Ivan Shishman (1371 – 1393) issued the Rila charter, sealed with a golden seal, granting the monastery 20 villages along with their lands as feudal possessions.

Boyana Church - Situated on the outskirts of Sofia, Boyana Church is composed of three buildings. The eastern church was constructed in the 10th century and was later expanded in the early 13th century by Sebastocrator Kaloyan, who commissioned a second two-story building adjacent to it. The frescoes in this second church, painted in 1259, are among the most significant collections of medieval paintings. The ensemble is completed by a third church, built in the early 19th century. This site is one of the most complete and well-preserved monuments of East European medieval art.