Greece Sailing Adventure: Cyclades Islands

Sail through the gorgeous Greek Islands on a ten-day seafaring adventure around the Cyclades. Setting off from Santorini, you’ll cruise the Aegean Sea in search of ancient towns, secluded coves and holiday hotspots like Mykonos and Paxos. Throw in some freshly caught seafood, local wines and a laidback way of life, and you’re set to drift and roll to the patterns of the ocean. Cool off with regular swims in turquoise seas and get the lay of the land from a local leader who’s got all the people in the right places.

Itinerary

Day 1: Santorini – Ios

Kalimera! Welcome to Greece. Your adventure begins in Santorini, where you’ll meet your skipper and fellow travellers at Cafe Spartakos at 1 pm at Athinios Port. If you’ve got time, consider arriving a couple of days early to see all that Santorini has to offer. There’s heaps of amazing restaurants, shops and bars in the island's capital, Thira, not to mention some of the most beautiful beaches and landscapes. Check out the volcanic beaches or take a walk along the caldera's rim to Firostefani, Imerovigli and Oia – this walk is also recommended at sunset, especially! After meeting your crew, you’ll board your yacht – your home for the next seven nights. You’ll sail to Ios’ port, where you’ll have some free time to explore the nearby beaches or check out Hora's shops, restaurants and bars – it’s all accessible within a short walk from the harbour.

Day 2: Amorgos

Sail to the rugged island of Amorgos. This is the stunning location of Luc Bresson's film, 'The Big Blue'. Stop for a swim at Paradisi Beach before continuing along the coast to the port of Katapola. The restaurants, cafes and bars along the waterfront are an excellent place to relax and enjoy views of classic Cycladic windmills and an old Venetian castle. You might like to explore the ancient Minoan Settlement or drive up to the 11th-century monastery, Moni Hozoviotissis, for beautiful views of the Aegean Sea. Maybe head to the village of Hora, sitting high up in the rocky mountainside. Stroll through the labyrinth of stone laneways and Byzantine churches surrounding the town square. The Amorgos Archaeological Collection is housed nearby in Gavros Tower.

Day 3: Small Cyclades

Cast off and sail to the Small Cyclades this morning. This group of islands are home to some small fishing villages as well as beautifully clear waters and beaches. While all these islands once harboured communities, the Middle Ages saw this reduced to just pirates and goats! Today, only Koufonisia, Iraklia, Schinoussa and Donousa have permanent residents, with the largest population said to be around 300. In the evening, maybe sample some fresh seafood in a waterfront taverna and sit back to enjoy the peace of the Mediterranean.

Day 4: Naxos

Today you'll make your way to the largest Cycladic Island of Naxos. There’s the option of taking a daytrip around the island, but you can always stay behind and relax. The island’s best beaches are to the south, where water sports are also on offer. Maybe hike up to the old Roman Catholic neighbourhood of Kastro, where winding laneways, mansions and churches all retain a medieval feel. While here, stop by the Roman Catholic Cathedral in the square, and the nearby Archaeological Museum, in the former Jesuit School of Commerce. Take an optional trip to the countryside to observe rural life, see one of the oldest temples in Greece and have lunch in the hills at a family tavern. Tonight, taste the local brew with a shot of Kitron (lemon liquor).

Day 5: Syros

Sail to the island of Syros, dropping by the Bay of Gaidharos 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. Over the next two days, maybe catch a bus up the hill to the fortress-like village of Ano Syros and explore the town’s stone archways and narrow alleys (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. At night, maybe immerse yourself in local island life with an optional group dinner at a neighbourhood family's home. Tuck into some homemade cuisine made with fresh, seasonal ingredients and enjoy the views from the seafront.

Day 7: Mykonos

Head to Mykonos today – with a history of around 5000 years, the island is said to be named after Apollo's grandson. It was also the mythological base for a deadly battle between Zeus and the Titans, their giant petrified bodies forming the rocks of the island. Browse the galleries and boutiques in town, see the unique architecture of the Church of Panagia Paraportiani or relax on one of the island’s white beaches. Tonight, maybe wander down to Little Venice, where colourful wooden balconies hang precariously over the sea – this is the ideal spot to sit back with a cocktail and enjoy the Aegean sunset. After, join the fun of Mykonos’ notorious nightlife.

Day 8: Sifnos

Set sail for the island of Sifnos, known for its production of high-quality ceramics. The island's bare hills contrast the fertile valleys of wild juniper, terraced olive groves and almond trees. The beach in the main port of Kamares is one of the best on the island and the ideal place to swim. Wander among the whitewashed houses, churches and chapels of the village of Apollonia – the capital of Sifnos. The Museum of Popular Art displays old photographs, textiles, costumes and pots. Climb up the headland for panoramic ocean views and see the medieval architecture of the fortress of Kastro.

Day 9: Folegandros

Sail towards the tranquil island of Folegandros this morning. Named after the son of a former King of Crete, Folegandros has suffered a long history of colonisation and occupation like many of the surrounding islands. In the port of Karavostasis, the pebbly beach or waterfront tavernas are nice places to relax. Take a stroll through the island’s capital of Hora – one of the oldest villages in the Cyclades. The area in and around the Kastro is the most striking. In the evening, maybe wander up the hill to the Church of the Panagia – an excellent vantage point to view the sunset.

Day 10: Santorini

Bid farewell to the open water as you catch the ferry back from Ios to Santorini, arriving back at Athinios Port just before 12 pm. With no other activities planned, your adventure ends today in Santorini. Your skipper can assist with organising a taxi to drop you off at your hotel or Santorini International Airport. If you would like to extend you stay, just get in touch with your booking agent ahead of time.

Departure Dates