Ano Syros crowns the hill directly above the port of Ermoupoli, reachable by a ten-minute bus ride or a steep twenty-minute climb up stone stairs. Founded by the Venetians in the thirteenth century, this fortified medieval settlement remains the Catholic heart of Syros and the birthplace of Rebetiko composer Markos Vamvakaris. Ano Syros is worth visiting if you want to walk car-free marble alleys and hear live bouzouki music in hillside tavernas. Look elsewhere if you need direct beach access, level walking paths, or late-night resort clubs.
Last updated 20 Sept 2026
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Ano Syros is a tiered amphitheatre of whitewashed stone, rising above Ermoupoli without a single car inside its walls. The day revolves around climbing quiet stairways, ducking through low medieval archways, and settling into shaded courtyard cafes. It suits travellers who appreciate unhurried afternoons, local music history, and sweeping views across the Cyclades rather than beach loungers and hotel swimming pools.
Take the morning bus from Ermoupoli to the top gate, exploring the Cathedral of Saint George before tourists arrive. Spend the afternoon at the Markos Vamvakaris Museum, then take an outdoor table at Taverna Lillis for fennel pies and cold wine as the island lights flicker on below. Select 1 Day above to see it.
A second day lets you descend the northern slopes toward the quiet agricultural valley of Episkopio. Return to Ano Syros by late afternoon to eat San Michali cheese and stewed beef with orzo at a family-run kafenio along Piatsa, where the bouzouki players set up after dark. Choose 2 Days to expand the plan.
With three days, hike the ancient mule track past Chalandriani to the prehistoric ruins of Kastri on the rugged north coast. Spend your final evening lingering over grilled local sausage and herbal raki at a quiet tavern perch while the ferry horns echo in the harbour.
Listen to Rebetiko played on bouzouki in open tavernas, honouring Markos Vamvakaris who codified the urban folk style here in the twentieth century.
Climb to the seventeenth-century Cathedral of Saint George at the summit, alongside historic Capuchin and Jesuit monasteries along the ridge.
Sample San Michali, a sharp, unpasteurised cow milk cheese aged for months, paired with local thyme honey and sweet loukoumi from Ermoupoli.
Order slow-braised goat with potatoes, fennel fritters, and sun-dried mackerel at stone terrace tables overlooking the Aegean below.
Navigate the medieval maze of Portara gates, covered archways, and chalk-white alleys built without streets to confuse Aegean pirate raiders.
Drink glasses of dry Serifiotiko and crisp Assyrtiko produced from drought-resistant island vineyards on Syros and neighbouring Tinos.
Look out across the port of Ermoupoli below, tracing nineteenth-century shipyard docks that once anchored Aegean trading fleets.
Visit the compact Markos Vamvakaris Museum, housing the musician's handwritten lyrics, personal effects, and photographs in a restored stone house.
Stand on the terrace of San Tzortzis at dusk for panoramic views stretching across the Aegean Sea toward Delos, Mykonos, and Tinos.
Pick up boxes of powdered loukoumi flavoured with rosewater and mastic, along with halvadopita wafers filled with nougat and toasted almonds.
Follow stone paths north out of the upper gate toward the rural hamlets of Episkopio and Chalandriani along ancient terraced hillsides.
Seek out small workshop doorways along the main alley selling hand-turned olive wood spoons, woven textiles, and painted ceramic tiles.