Konavle is the long, fertile valley that runs south east of Dubrovnik towards the Montenegrin border, and St. Barbara is a small church at Dubravka, near its upper edge, surrounded by a field of medieval tombstones. These stećci, heavy carved blocks of limestone dating from the late Middle Ages, are part of the cross-border UNESCO listing of stećci cemeteries shared by Croatia, Bosnia and Herzegovina, Montenegro and Serbia. The Dubravka group is one of the most accessible in Croatia, and the setting, with the church, the old stones and the view over the valley, is quietly beautiful.
Konavle has always been a borderland. For centuries it belonged to the Republic of Ragusa, the merchant state of Dubrovnik, which bought it in the fifteenth century from Bosnian nobles. The valley supplied the city with wine, olive oil and food, and its villages kept a strong folk culture, with embroidered costumes, songs and dances that are still performed at festivals and on Sundays in Čilipi. High on a crag above the valley stands Sokol Grad, a fortress built into the rock that guarded the routes from the hinterland and has been restored and opened to visitors.
The riding here has two faces. The main coastal road from Dubrovnik to the border at Debeli Brijeg is busy, especially in summer, with tourist traffic and trucks, and the airport at Čilipi adds to the congestion. The smaller roads through the valley and up into the hills are another matter: narrow, winding, quiet, passing through vineyards, olive groves and stone villages, with views over the sea. The road up towards the border with Bosnia and Herzegovina climbs steeply into bare karst, and the view back over the valley and the coast is superb.
Cavtat, about seventeen kilometres away, is a pretty harbour town with restaurants, cafes and hotels, and it makes a good base. Herceg Novi, just across the Montenegrin border, is the nearest larger town on that side, with fuel and all the services you might need. Remember that crossing between Croatia and Montenegro means an external Schengen border, so allow time for checks in summer. The local wine, especially the indigenous malvasija of Dubrovnik, deserves a glass at the end of the day.