Ancient Macedonia

This 14-night tour travels through the lands once ruled by the Ancient Macedonians, starting in Sofia where Roman ruins sit alongside onion-domed churches and Soviet relics. From there the route crosses into North Macedonia to stay near the Saint Joakim Osogovski Monastery, notable for its 18th-century frescoes. The small volcanic town of Kratovo with its Ottoman towers and stone bridges follows before the capital, Skopje, offers Ottoman bazaars and a half-day in the karst-cut Matka Gorge.

The journey continues around Lake Ohrid, a UNESCO World Heritage Site, with walks past its many churches and a possible day trip into Albania. After venturing into Galicica National Park and visiting sites connected to Alexander the Great and his father Philip II, the tour reaches Thessaloniki with its Roman monuments and the Royal Tombs at Vergina. An island day on Thassos and medieval monasteries in Bulgaria bring the route to its end back in Sofia, a city offering a few last hours for exploration.

Explore Worldwide’s escorted style balances historical landmarks and natural beauty with small-group local experiences. Expect a steady pace and varied landscapes, from mountain monasteries to lakeshores, with the odd unexpected detail: such as Skopje’s law on mosque height shaping its skyline.

New to Greece? Our Greece guide has the practical essentials: money, plugs, visas and when to go.

These are the places the trip visits, in order. Explore Worldwide publishes the day-by-day itinerary on its own site.