The Cyclades are known for their rugged beaches and iconic blue-and-white stucco buildings — until you arrive in the main town of Hermoupolis on the Greek island of Syros, that is. The bustling port city is an energised contrast from its Cycladic neighbours, where neoclassical mansions in a pastel palette cascade down to concrete swimming platforms (the places to be seen during the summer months), and a colourful hotel filled with contemporary art awaits.
Hermoupolis has a rich history. It was under Venetian occupation for 300 years, before becoming the cultural and commercial shipping centre of Greece in the 19th century; a lucrative and multicultural past which is reflected in the Venetian-style houses, marble paved streets and abundance of both Orthodox and Catholic churches. There is much to discover in this sprawling yet walkable city which feels like its own cultural pot compared to the rest of the Cyclades.
Day One, 2pm
Located so close to Mykonos, Tinos and Paros, Hermoupolis’ port is a busy one with plenty of ferries stopping en route between the nearby islands and Athens. Take a five-minute taxi drive from the ferry to the Vaporia district, where you will be greeted at Aristide Hotel, one of the very best new hotels in Greece.
Housed in a former shipowner’s mansion, Aristide (owned by author and hotelier Oana and her sister Jasmine) has just nine suites spread over its three floors (three of which flaunt private terraces and plunge pools). Each suite is named after the provenance of the marble adorning its bathrooms and furniture. Jewel-coloured paint and an eclectic collection of contemporary artworks brighten the walls of both the bedrooms and communal areas of the hotel; the cherry on the cake is the iconic roof terrace restaurant with views of the surrounding skyline and the silhouettes of the neighbouring islands in the distance.
Day One, 4pm
After sipping a refreshing welcome drink of the hotel’s homemade lemonade in the luscious garden terrace and checking into your suite, grab your towel and stroll just five minutes down the road to the ‘beach’.
Don’t expect long sandy beaches here — Vaporia and Asteria beaches are concrete slabs nestled below the iconic neoclassical mansions of the town above, with ladders leading down into the crystal-clear waters. Bring a snorkel and you’re likely to spot fish, sea urchins and perhaps even octopus scurrying across the rocks below.
Day One, 7pm
Book a table for cocktails and dinner on the hotel’s rooftop as dusk sets in. Head chef Petros Braikidis has garnered rave reviews in the past couple of years thanks to his creative take on traditional Greek cuisine. The menu expertly balances vegetarian, seafood and meat dishes, offering something for everyone, yet with a refined touch.
Day Two, 9am
Enjoy breakfast in the hotel’s garden terrace, surrounded by fragrant greenery. The extensive menu includes Cycladic classics and local delicacies, leaving you spoilt for choice. Afterwards, take advantage of the cooler morning temperatures to wander up one (or both) of the two hills that loom over the city. Each hill has its own church perched atop — the Roman Catholic Church of St George and the Orthodox Church of the Resurrection.
DAY TWO, 12PM
Stroll down towards the harbour, where you’ll discover labyrinthine streets and alleys, shaded from the sun by bougainvillaea and packed with bars and cafés. Stop for a light lunch in one of the many traditional tavernas, pop by café-meets-gallery Plastico for the best local coffee, and don’t miss Django Gelato for delicious ice-cream with refined flavours such as smoked hazelnut and raw salted pistachio.
There is much to discover in this sprawling yet walkable city which feels like its own cultural pot compared to the rest of the Cyclades.
Day Two, 4pm
Every Tuesday, Aristide hosts ‘picnics’ for their guests, local residents, and fellow travellers in the grounds of a private neoclassical mansion. These memorable feasts are not to be missed, as not only do you get to sample more of Petros Braikidis’s cooking (a 10-course banquet grilled on a barbecue) but you have the chance to mingle with interesting people over the long communal table, before exploring the vast grounds of the faded grandeur mansion. Chances are that you will bond with the other diners over dinner and continue the conversation with cocktails on the roof terrace when you return to the hotel.
DAY THREE, 10AM
Following one last breakfast in the garden, spend your final hours on Syros exploring more of Hermoupolis — if you can tear yourself away from the swimming platforms. Meandering into town from the hotel, first visit the Church of Agios Nikolaos. If its imposing blue dome and neoclassical architecture seem impressive from the outside, wait until you feast your eyes on the stained-glass windows and star-covered ceiling inside. Don’t miss the Apollon Theatre (constructed as a miniature of La Scala in Milan) and Maiouli Square, where you’ll find the City Hall (designed by architect Ernst Ziller). Pop into XIMAPIA art and craft store, Kissyris (handcrafted jewellery) and Hydora Concept Store to pick up stylish souvenirs before heading for the ferry.
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