Day 1 — Alexander Nevsky & the City Centre
Start at Alexander Nevsky Cathedral, one of the largest Orthodox cathedrals in the world and the image most people carry away from Sofia. The crypt's icon collection is exceptional. Behind the cathedral, St Sofia Church is older and plainer but gave the city its name.
Spend the rest of the day walking the centre: the National Assembly, the Ivan Vazov National Theatre, and the National Garden, then lunch and an afternoon browsing shops and cafés on Vitosha Boulevard. Dinner at a mehana — shopska salad, kavarma, and rakiya — is the reliable choice for a first night.
Day 2 — Serdica, the Largo & Communist Sofia
Sofia's Roman past is everywhere once you start looking. Serdika metro station has ruins under the platforms; the open-air complex by the Sheraton Sofia exposes a 4th-century forum and the Rotunda of St George, a red-brick building that has served as Roman temple, mosque, and church across nearly two millennia.
Walk the Largo, the Stalinist-era government complex, and watch the changing of the guard outside the Presidency. In the afternoon, visit the Museum of Socialist Art — a sculpture park of relocated communist-era statues, including the giant red star that once crowned the Party House — one of the more direct ways a former Eastern Bloc capital confronts its recent history. Relaxed dinner in the centre to close the day.
Day 3 — Boyana Church & Vitosha Mountain
Morning: Boyana Church, a UNESCO World Heritage Site at the foot of Vitosha, with 13th-century frescoes considered among the finest surviving medieval paintings in Europe. Visits are timed and limited to small groups — book in advance.
From Boyana, continue up into Vitosha Mountain itself. Take the gondola from Simeonovo to Aleko and walk out to the Golden Bridges, a striking river of granite boulders, or tackle a trail towards Cherni Vrah, the mountain's 2,290m summit — even a short walk gives sweeping views over the whole city. Return to Sofia by evening for dinner.
Day 4 — Museums & Neighbourhood Sofia
Morning: the National History Museum on the southern edge of the city holds the finest collection of Thracian gold and silver in the world, including the Panagyurishte Treasure, a 6kg gold drinking set from the 4th century BC.
Afternoon: explore beyond the tourist centre — Oborishte and Lozenets are residential districts with leafy streets and specialty coffee shops, a good sense of how Sofians actually live. The nearby Zhenski Pazar market is worth a walk-through for fresh produce and cheap street food.
Evening: a wine-focused restaurant in the centre and a Bulgarian Mavrud or Melnik red, both underrated varieties rarely seen outside the country.
Day 5 — Rila Monastery Day Trip
Rila Monastery is Bulgaria's most important religious site and one of the country's great architectural set pieces — a 10th-century Orthodox monastery rebuilt in the 19th century, tucked into a steep, forested valley in the Rila Mountains about two hours south of Sofia. The striped arcades of black-and-white stone, covered in vivid frescoes, surround a courtyard dominated by the Hrelyo Tower, the only structure to survive from the medieval original.
Buses run from Sofia's Ovcha Kupel station most mornings, or book an organised day tour. Give yourself at least two hours at the monastery — the museum holds Rafail's Cross, a walnut-wood crucifix carved with over 1,500 miniature figures by a monk who reportedly went blind finishing it.
Return to Sofia by early evening for a final dinner — this is the trip's natural high point, and a good note to end a five-day visit on.