Bachkovo Monastery, Asen's Fortress and Plovdiv from Sofia
Start your trip from Sofia around 8:30 a.m. The distance to Bachkovo is 151 km. First, take the Trakia Highway towards Plovdiv, then continue to the exit for Asenovgrad. It takes less than two hours to get there.
See the Bachkovo Monastery, a major Eastern Orthodox monastery in Southern Bulgaria. It is located on the right bank of the Chepelare River, about 10 km south of Asenovgrad. The monastery is a unique combination of Georgian, Byzantine, and Bulgarian culture. If you are interested in the history of this unique monument, a local guide can tell you its inspiring story.
The monastery region abounds with traditional restaurants where you can have lunch.
Right after lunch, head towards Asen's Fortress, another historical must-see sight. It is located in the Bulgarian Rhodope Mountains, 2-3 km south of Asenovgrad. Spend about an hour there, enough time to walk around and climb to the top of the fortress. It was built on the hill above the road to guard the canyon against conquerors.
At the end of the trip, you could stop in Plovdiv for a short break of about an hour before returning to Sofia. Ideally, you should reach Sofia between 7:30 and 8:00 p.m.