
Sofia
A capital with no single central square: Roman Serdica sits under a glass floor in the pedestrian zone, and a synagogue, a mosque and two churches stand a few minutes' walk from each other. Vitosha mountain starts where the city ends.
A capital, a Roman city, a medieval fortress and the sea — in a line that never doubles back

Bulgaria here is not one coastal route but four cities that share very little: Sofia is the gateway, Plovdiv is a Roman city still lived in, Veliko Tarnovo is a medieval capital on a cliff, and Varna is the only one of the four on the sea. The order in this guide runs one way, from the interior to the coast, and never loops back to the start.
The difference between these four cities is bigger than in most countries on this site. Sofia is the largest and flattest, with a metro and wide boulevards — a city you cross on foot in kilometres, not one built around a single square. Plovdiv stands on six hills, and the whole old town can be covered on foot in a day. Veliko Tarnovo is the steepest of the four — streets run up and down the Yantra river canyon, so two blocks of distance can mean a real climb. Varna is the only one on the sea: a beach town in summer, a port and university town the rest of the year.
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Sofia and Varna each have their own airport (SOF and VAR), so it's possible to fly into one city and out of the other without returning to the start. Plovdiv's own airport has only limited seasonal traffic and Veliko Tarnovo's has no scheduled passenger flights, so both are reached from Sofia: the train to Plovdiv takes 2 h 40, the direct coach to Veliko Tarnovo about 3 h 20 — both routes start in Sofia, not in each other. A direct train and coach also run on to Varna from Veliko Tarnovo, though less often than the lines to Sofia — a car or an organised tour remains the more practical choice for that stretch. Also: e-vignette required on motorways.
The alphabet took its final form in the late 9th century at the Preslav Literary School, in the First Bulgarian Empire, through the work of the disciples of Cyril and Methodius. Bulgaria marks 24 May every year as the Day of Slavic Alphabet and Culture.
The necropolis near Varna dates from around 4600 BC, and it produced the oldest worked gold ever found — older than the Egyptian pyramids. Part of the find is on display in Varna's Archaeological Museum.
Traditionally in Bulgaria a nod up and down means "no", and a shake left and right means "yes" — the reverse of most of Europe. The habit is fading in tourist spots but still catches people out in smaller towns.
Around Kazanlak, the pink damask rose has been picked for rose oil for centuries, a raw material for perfume exported worldwide from here. The harvest is short, in May and June, done early in the morning while the flower is still fresh.
Archaeologists date settlement on the site of Plovdiv to the sixth millennium BC, ranking it among Europe's oldest continuously inhabited towns — older than Rome, Constantinople or Athens.
Rila Monastery was founded by Saint Ivan of Rila in the 10th century, as a hermit's cell in the mountains. It has been a UNESCO World Heritage Site since 1983 and is Bulgaria's largest Orthodox monastery.
This isn't a ranking — it's a route. Any one of these could carry a whole trip.

A capital with no single central square: Roman Serdica sits under a glass floor in the pedestrian zone, and a synagogue, a mosque and two churches stand a few minutes' walk from each other. Vitosha mountain starts where the city ends.

Six hills, a Roman theatre still used for concerts, and the Kapana district, which went from an abandoned craftsmen's quarter to the city's densest cluster of cafés. Smaller than Sofia and walkable in a day.

A town tilted over a canyon: the Old Town houses sit on terraces above the Yantra river, and the Tsarevets fortress is visible from almost anywhere. It was the capital of the Second Bulgarian Empire until the Ottomans took the city in 1393.

The only one of the four on the sea, and besides Sofia the only one with its own airport. The Sea Garden park runs the length of the shore, and the town behind it is low-rise and walkable in half a day.
Short answers to what people ask most before setting out.
No: Sofia is best May–Jun · Sep, Plovdiv and Veliko Tarnovo Apr–Jun · Sep–Oct, and Varna, because of swimming, only Jun–Sep, peak Jul–Aug. There's no single date range that suits all four.
Yes: e-vignette required on motorways. Inside the cities, no — Sofia has a metro, Plovdiv and Veliko Tarnovo are walkable, and Varna has city buses to the beaches. A car mainly helps for trips off the main public transport lines.
By train and coach, via Sofia: the train to Plovdiv takes 2 h 40, the direct coach to Veliko Tarnovo about 3 h 20. The last leg, from Veliko Tarnovo to Varna, is a direct train or coach, and Varna's own airport means flying home without going back to Sofia.
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All photographs come from Wikimedia Commons and are used under the licence stated beside each one.