Syros City Tour: Medieval Ano Syros

Harborfront Views of Beautiful Syros Island
Discover the winding alleys of the medieval city, Ano Syros. This historic settlement is strategically set on a hillside with the impressive San Giorgio's Cathedral at its highest point. Your tour will start here so that you can enjoy incredible views and meander down the hilly streets.

The famous cathedral was once designated as the center of Catholicism in the Aegean Sea. You can also visit the monasteries of the Jesuits and the Capuchins, which were also once the powerhouse of Ano Syros. As you stroll through the narrow, cobbled streets, stop at some of the other churches, such as the Catholic Church of San Sebastian.

As you continue to the main square, visit the Markos Vamvakaris Museum. Here you'll find a tribute to one of the oldest and most important bouzouki players in Greece. Rest your feet and fill your belly for lunch at a local restaurant. You'll dine with a stunning view of Hermoupolis, its port, and the Aegean Sea. On the way back to your accommodation, make one final stop at the renovated Anemomilos Windmill.

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Itineraries with Syros City Tour: Medieval Ano Syros

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These four Cycladic islands haven't graced as many guidebook covers as their glitzier cousins, but that just means there's more here for you to discover without battling hordes of selfie sticks. Take 10 days to tour Syros, Tinos, Naxos, and Ios on this itinerary, with pilgrimage sites, culinary experiences, and more.

Sailing Holiday in the Aegean - 9 Days

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Sailing the Greek Cyclades: Paros, Mykonos, Serifos - 8 Days

As the ultimate sailing adventure through Greece's coveted Cyclades Islands, this tour combines bustling city life with tranquil villages nestled in the Aegean Sea. From some of Europe's best nightlife to humble fishing towns and secluded beaches, travelers will enjoy Greece's rich and varied heritage. Enjoy sunsets and local seafood while discovering important and ancient archeological sites, all from the comfort of a private yacht.

Gastronomy and Culture of the Cyclades - 12 Days

Discover Greece's distinct culture and gastronomy, starting in Athens with a private tour of the Acropolis and a hands-on cooking class, followed by a transition to some of the most beautiful islands of the Cyclades. Begin in Syros for food tours and explorations of medieval cities, then head to the hidden gem of Tinos for some of Greece's best cuisine, plus a visit to marble villages, an art workshop, and an afternoon swimming in the Aegean Sea. End your trip in Naxos where you'll discover ancient sites, historic streets, medieval monasteries, and, of course, delicious, locally-sourced cuisines, the pride of the Greek Islands.