Asenovgrad

Ruins of a medieval fortress perched on a steep rocky ridge. An inscription carved into the rock testifies that the fortress was strengthened in 1231 by the Bulgarian ruler Ivan Asen II, hence the name. Like most Bulgarian fortresses, only very basic ruins remain, with some modern reconstructions. The site's centerpiece is a fortified church overlooking the precipice. It had survived mostly intact until 1928, when an earthquake collapsed its dome, necessitating reconstructions in later years. There's a parking lot and a tiny on-site museum. One of the 100 Tourist Sites of Bulgaria.

The second largest functioning Eastern Orthodox monastery in Bulgaria after the Rila Monastery, in a picturesque spot among the mountains. Established in the 11th century, it has been sacked and rebuilt several times. The only original building to survive is the Ossuary; the monastery's Cathedral Church of the Dormition was built in 1604. Getting there is extremely easy, as buses on the route Plovdiv-Smolyan stop in both Asenovgrad and Bachkovo. Tell the driver you are going to the monastery (simply saying "Bachkovo Manastir" should do the trick) and he may drop you off right in front.