Greece Sailing Adventure: Cyclades Islands

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Day 1: Santorini – Ios
Welcome to Greece! Meet your skipper and fellow travellers at Cafe Spartakos at 1 PM at Athinios Port, Santorini, before taking a ferry to Ios, where you'll board your yacht. If you have time, consider arriving a couple of days early to enjoy Santorini's charm. Explore the island’s capital, Thira, with its array of restaurants, shops, and bars. Don’t miss the stunning walk along the caldera’s rim to Firostefani, Imerovigli, and Oia, especially memorable at sunset—just be sure to leave enough time to avoid walking in darkness. Santorini’s volcanic beaches are also a must-see. After your welcome meeting, settle into your sailing yacht and enjoy some free time to explore Ios, including its beautiful sandy beaches or the lively shops and bars in Hora, all within a short walk from the harbour.

Day 2: Amorgos
Sail to the rugged island of Amorgos (approximately 4 hours), the stunning backdrop for Luc Besson's film "The Big Blue." Enjoy a swim at Paradisi Beach before heading to the port of Katapola. Relax at the waterfront cafes and restaurants, taking in views of classic Cycladic windmills and an old Venetian castle. You might explore the ancient Minoan Settlement or drive to the breathtaking 11th-century monastery of Moni Hozoviotissis for spectacular Aegean views. Be sure to visit the village of Hora, perched on the mountainside, where you can wander through charming stone alleyways and admire the Byzantine churches surrounding the town square. The nearby Gavros Tower houses the Amorgos Archaeological Collection.

Day 3: Small Cyclades
Set sail for the Small Cyclades this morning (approximately 4 hours). This group of islands features quaint fishing villages, clear waters, and beautiful beaches. While once home to bustling communities, these islands are now primarily known for their serenity, with permanent residents numbering around 300 on Koufonisia, Iraklia, Schinoussa, and Donousa. In the evening, consider dining on fresh seafood at a waterfront taverna, soaking in the peaceful Mediterranean atmosphere.

Day 4: Naxos
Today, you'll head to Naxos, the largest island in the Cyclades. You have the option to take a day trip around the island, or you can relax and enjoy your surroundings. The best beaches are to the south, where water sports are also available. Perhaps hike to the old Roman Catholic neighborhood of Kastro, where medieval charm abounds in its winding lanes, mansions, and churches. While there, visit the Roman Catholic Cathedral and the Archaeological Museum, located in the former Jesuit School of Commerce. Consider an optional trip to the countryside to witness rural life, see one of Greece's oldest temples, and enjoy lunch at a family tavern. Don't miss a taste of the local Kitron liqueur. In the evenings, experience the vibrant nightlife of Hora.

Day 5-6: Syros
Sail to the island of Syros (approximately 4 hours), stopping at the Bay of Gaidharos for a swim. Known for its relaxed atmosphere and neoclassical architecture, Syros played a neutral role during the Greek Revolution, becoming a refuge for those persecuted. You can catch a bus to Ano Syros, a fortress-like village with stunning views of the Aegean, and explore its stone archways and narrow streets. Sample authentic Greek cuisine and soak up the local culture in the capital of Syros and the Cyclades, Ermoupoli, where you can admire the magnificent town hall in the main square.

Day 7: Mykonos
In the morning, set sail for the glamorous island of Mykonos (approximately 3 hours). With a history spanning around 5,000 years, Mykonos is named after Apollo's grandson and was the site of a mythological battle between Zeus and the Titans, whose petrified bodies formed the island's rocks. Explore chic boutiques and galleries, marvel at the unique architecture of the Church of Panagia Paraportiani, or relax on one of the island’s pristine beaches. In the evening, head to Little Venice, where colorful wooden balconies overlook the sea—an ideal spot to enjoy a cocktail and watch the sunset. Afterward, dive into Mykonos' vibrant nightlife.

Day 8: Sifnos
Set sail for Sifnos, renowned for its high-quality ceramics. The island’s arid hills contrast with its lush valleys filled with wild juniper, terraced olive groves, and almond trees. The beach at Kamares, the main port, is one of the island’s best spots for a swim. Stroll through the village of Apollonia, Sifnos' capital, characterised by its whitewashed houses and churches. Don’t miss the Museum of Popular Art, showcasing photographs, textiles, and ceramics. Hike up to the headland for panoramic views and visit the medieval fortress of Kastro.

Day 9: Folegandros
This morning, sail to the serene island of Folegandros. Named after a former King of Crete's son, Folegandros has experienced a long history of colonization and occupation, much like its neighbouring islands. At the port of Karavostasis, you can relax on the pebbly beach or visit a waterfront taverna. Take a leisurely walk through Hora, one of the Cyclades' oldest villages, with its striking architecture around the Kastro. In the evening, hike up to the picturesque Church of Panagia for a stunning sunset view.

Day 10: Santorini
Say goodbye to the open water as you catch the ferry back from Ios to Santorini, arriving at Athinios Port just before noon. With no further activities planned, your adventure concludes upon arrival. Your skipper can assist you in arranging a taxi to your hotel or Santorini International Airport.