From Sofia: Serbia and Macedonia Guided Tour

An English-speaking guide will pick you up from the meeting point in Sofia at 9:00AM and, after about a 2-hours drive with various landscapes to admire along the way, you will reach the Serbian border. After crossing the border you will go the nearby town of Bosilegrad (the former Yugoslavia's main state) before you cross back over the border with Bulgaria and head for Northern Macedonia. After another short drive, you will arrive at the beautiful Monastery of Osogovo – an incredibly powerful place in the hills from the 12th Century, which was later turned into a mosque by the Ottomans, and then again converted into a church. This place is very scenic and peaceful - take time to go for a walk around the area. Afterwards, you will have lunch in a nice restaurant with good Macedonian grill (meat or fish) and Skopsko beer, of course. Please note that the total driving time is around 5 hours.