Tranquil vineyards and windblown ruins offer a tantalising glimpse of Bulgarian Thrace’s textured history. You can combine some of the best sights into a west–east road trip out of the city of Plovdiv.
First, drive west to Perushtitsa. The rust-coloured ruins of its Red Church create an enigmatic silhouette amid fragrant meadowlands. Its modern visitors' centre tells the story of this rare brick construction, dating to the 5th century, while wooden walkways allow access to the skeletal remains, where you can glimpse a few faint frescoes.
Stop in Perushtitsa town just 2km south for a quick spin around its historic sights. While the Historical Museum itself has little English-language signage to illuminate visitors, your ticket gives you access to two interesting sights nearby. The haunting Sveti Arhangeli Mihael Church is now a memorial to the horrific Ottoman massacre of insurgents and their families, who were walled up here during the April 1876 uprising; many committed suicide to avoid being slaughtered or imprisoned. Close by, the 1850-built Danov School hosts an interesting little museum to Revival education – complete with old-fashioned writing desks – within an elegant mauve building.
Drive 5km northeast along route 8602 into the tiny village of Brestovitsa, home to the world-class Todoroff Wine & Spa. Stop for lunch in the olde-worlde restaurant, or simply stock up on wine. You may also be tempted to linger for a luxurious stay and a wine-themed spa treatment (book ahead for treatments and wine tastings).
Fully rested, rejoin route 86 and continue east and south for 30km to reach Asen’s Fortress. Squatting precariously on the edge of a cliff, it offers panoramic views that will make your stomach flutter. Early incarnations of this structure were bulked up by Thracians in the 5th century BC. Over the centuries, Roman, Byzantine and Ottoman rulers admired its impenetrable position so much that they continued to build and rebuild, adding chapels and thickening its walls to a battering-ram-proof 3m. It's signposted ('Asenova Krepost') off route 86, which links Plovdiv and Bachkovo.
From Asen's Fortress, it's a 19km drive back north to Plovdiv, or else press further south to be rewarded by the excellent Bachkovo Monastery, 30km south of Plovdiv, and the wild promise of the Rodopi Mountains.