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.

Plovdiv, the second biggest city in Bulgaria, is considered to be one of the oldest settlements in Europe, with more than 7000 years of history. Plovdiv is situated on the crossroads between the West and the East, amid the fertile plain of Thrace, where history and modernity go hand in hand. See how culture and art have always thrived in this city as you explore a vivid medley of shapes, styles, and colors. The city is home to the fabulous remains of the Ancient Roman Empire – the Roman Stadium, the Roman Forum, and the Amphitheatre. During your time in the city, you can discover the Old Town of Plovdiv, situated on the three hills of the ancient Trimontium. See the houses from the National Revival period, which  have been proclaimed an architectural open air museum. Discover many of the main sights in the area with a guide.