Today, cast off and sail to the Small Cyclades, where only Koufonisia, Iraklia, Schinousa and Donousa have permanent residents. Here, you'll discover clear waters, great beaches, friendly locals and sleepy tavernas all built around the fishing villages. Explore the town, maybe sampling some fresh seafood in a waterfront taverna – a great way to take in the magic of the Mediterranean. Over the next few days, you’ll head to Amorgos, Naxos and Syros, depending on the weather and the wishes of the group.
The rugged mountainous island of Amorgos is known as the location of Luc Bresson's film 'The Big Blue'. Amorgos has a history of colonisation and occupation with evidence of a functioning society back as far as 4000 BC. At Katapola, the island's main port, you'll see classic Cycladic architecture with windmills and an old Venetian castle. Stroll the waterfront, explore the ancient Minoan Settlement or visit the village of Hora (Amorgos town) which sits high on the rocky mountainside. Maybe drive up to the 11th-century monastery, Moni Hozoviotissis, built gripping the cliff-face with panoramic views across the Aegean Sea.
Continue to Naxos for more beaches, villages and the fragrant olive groves of Hora (the capital). This place has a colourful mythological history and the Old Town is perfect for a stroll. Follow a pathway up to the impressive Venetian Kastro where mansions, monuments and churches all retain their medieval spirit in a mass of winding laneways. Stop by the old Roman Catholic Cathedral in the square, and the nearby Archaeological Museum which is housed in the former Jesuit School of Commerce. Maybe head into the countryside to see the local rural life, visit one of the oldest temples in Greece and chill out in the hills with lunch at a family tavern. Get a taste of the heady local brew, Kitron (best described as a lemon liquor), and top it off with a walk along the beach.
Sail to the island of Syros, dropping by the Bay of Gaidharos along the way for a swim. Known for its relaxed atmosphere and neo-classical architecture, Syros’ neutral role during the Greek Revolution made it a safe haven for the persecuted. You can catch a bus up the hill to the fortress-like village of Ano Syros and explore the town’s stone archways and narrow alleyways (the views of the Aegean are stunning from up here). Sample authentic Greek food and culture in the capital of Syros and the Cyclades, Ermoupoli, and check out the town hall in the main square.