Sailing the Cyclades – A Luxury Travel Blog : A Luxury Travel Blog

The beauty of chartering a yacht in Greece is the freedom to go from island to island wherever you feel like. In the Cyclades, the warm, calm waters and stretches of sandy beaches are a big draw, along with the cool seaside vibe found in sleepy towns. This group of islands spread across the central Aegean Sea is close to Athens and benefits from the Meltemi winds, ideal for water sports enthusiasts. Expect fresh cuisine from the sea, genuine hospitality and stunning scenery – renting a yacht here is a truly magical experience.

Kea and Kythnos

Gateway to the Greek mainland, unspoilt Kea stands out from the crowd, characterized by steep mountains, olive groves and off-the-beaten-path beaches. She walks through the main gates of the pedestrian city of Ioulida, where the famous statue of the smiling lion and the local museum are well worth a visit. The laid-back paradise of Kythnos embraces beach life entirely, offering countless stretches of sand accessible only by yacht and crystal-clear waters to intrigue divers. Added value is found in Oria Castle, Katafigi Cave and the stone-enclosed hot springs at Loutra.

Andros and Tinos

Northernmost Andros boasts lush hillsides, meandering rivers, and golden sands. Located on a peninsula between two long stretches of beach, Chora, the main pedestrian area, bustles with delicious cafes and shops, while a diverse collection of art museums, monasteries and ancient sites are found throughout the island. A privileged place for lovers of activity is Ormos Beach for windsurfing. Nearby, and comparatively unknown, charming Tinos is packed with old-style whitewashed houses and secluded beaches. Enjoy delicious architecture, traditional culture and provincial food festivals.

Syros and Seriphos

For a bit of quiet away from it all, head to culturally significant Syros. The capital, Ermoupolis, exudes the romance of a bygone era among its doughy-toned neoclassical houses, narrow streets and squares dotted with cafes, but don’t miss the famous casino if you’re feeling lucky. With several beautiful beaches, the protected cove of Galissas is a must-see. Beautifully laid-back Serifos is a yachting paradise packed with endless charm, thanks to sheltered bays and stretches of beach. Head up the hillside to stroll through Chora main and enjoy stunning panoramic views at the top while enjoying a Tsipouro at an outdoor cafe.


Popular for its chic boutiques, chic beach clubs and buzzing nightlife, Mykonos’ whitewashed paradise has a picturesque edge. Visitors can enjoy sheltered anchorages, picturesque bays and some fantastic beaches. Whimsical Little Venice enchants with its hanging medieval buildings, while the maze of narrow streets of elegant Mykonos Town exudes charm. Whether you’re looking for a laid-back retreat or a cosmopolitan vibe, countless beaches provide the required frame of mind; as you head inland, the leafy slopes are dotted with quaint villages. Nightly entertainment caters to all tastes, with large beach clubs, champagne bars and cabaret shows keeping the action going until dawn.

Stops and Antistops

Sugar cube villages, ancient ruins and lively taverns nestled in the natural landscape make Paros a quintessential Greek island. Countless opportunities present themselves to anchor and snorkel in secluded crescent-shaped bays ringed by swaths of velvety sand, while water sports enthusiasts flock to Golden Beach. Ashore at Parikia, the maze of narrow whitewashed alleys is a big draw during the day: visit characteristic Lefkes to see handcrafted pottery, soak up exquisite countryside views, and soak up the heady fragrance of jasmine in the air.

Explore the nearby island of Antiparos, with its traditional whitewashed villages, deserted beaches, and a magical cave system on the south side. The attractive 15th century castle is also worth a visit.


The largest of the island group, Naxos lays claim to the highest peak in the Cyclades of Mount Zas, set amid winding hiking trails and fertile valleys dotted with vineyards. The coast is lined with exotic beaches, exciting shipwreck dives and cozy seaside tavernas, not forgetting the windsurfing paradise on the west coast. Compared to its bustling counterparts, laid-back Naxos remains relatively unknown: step back in time to mountain villages where self-sufficient locals still wear traditional clothing, woven on ancient looms. Summer entertainment abounds at Bazeos Castle with performances and displays and the Panigiri festival celebrations are particularly significant at Filoti.

Sifnos and Milos

Cycladic elegance prevails in Sifnos: whitewashed terraces, terracotta fireplaces, and vibrant bougainvillea reflect the refined yet relaxed atmosphere. At Panagia Chryssopigi, thrill-seekers plunge from rocky outcrops, while secluded Fykiada Bay is perfectly accessible by yacht. Foodies take note: in September, the annual food festival in Sifnos further promotes the island’s rich culinary tradition. Unique Milos, birthplace of Aphrodite and original home of the Venus de Milo, exudes natural beauty. From the volcanic sunsets of Plaka, the pirate caves of Kleftiko, to the charming fisherman’s boathouses in Klima, this island is a treasure chest of hidden gems.

Sikinos and Folegandros, Amorgos and Ios

Small and quaint, peace abounds in charming Sikinos. The popular hiking trail to the ancient Episkopi Monastery offers stunning views, while four secluded coves offer secluded beaches, perfectly accessed by yacht. Rocky Folegandros, famous for its exquisite sunsets, is the antithesis of Santorini and Mykonos. With no airport and just three towns, the ancient ruins transport you back in time, while the secluded crystalline coves and prehistoric caves are truly captivating. On the southeastern edge of the Cyclades, remarkably unspoiled Amorgos is rich in both beauty and culture. Enjoy the glorious Aigialis beach, visit the famous Hozoviotissa Monastery with achingly beautiful views, and taste the delicious local Ladotýri cheese. In contrast, the most fun island of Ios is full of high-paced action. If nightlife is a low priority, enjoy the beautiful Magganari beach and explore the city’s windmills.


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The best way to reach it is by sea through the immense volcanic caldera, Santorini is undeniably spectacular and needs no introduction. Whitewashed cubical houses perch on the hillside, intricately linked by cobbled alleys, while below the coastal beaches, individually toned with red, white and black sand, add colorful appeal. Cruise past uninhabited Aspronisi and Strogili, take a therapeutic bath in the hot springs of Nea Kameni, and admire Akrotiri’s cliff-top lighthouse and ‘Indian Rocks’ formation. Be sure to head to the picturesque town of Oia, the best place to see Santorini’s famous sunset.

One beauty of sailing the Cyclades is the complete freedom to take your time exploring, as your captain and crew can tailor an itinerary to suit all personal preferences. The beaches are one of the biggest attractions in the Aegean, with velvety sands and warm waters that make chartering a yacht a wonderfully relaxing experience to enjoy with your partner, friends or family.

Nicholas Dean is managing partner of Ocean Independence. Ocean Independence is a world leader in luxury yachts, providing a personalized experience in yacht charter, sales and management.

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