Lying in the circle at the heart of the Aegean, the islands of the Cyclades sparkle with infinite appeal. Their steady winds, dramatic landscape and natural harbors make them an idyllic sailing destination. Each island is unique and surprisingly different, but they all share an astonishing wealth of historical sites and architectural wonders left by ancient civilizations during five millennia. From the cosmopolitan islands of Mykonos and Santorini to the lesser-known islands of Paros and Naxos, these islands abound with simplicity and charm.
Follow in the footsteps of Jackie Kennedy and Aristotle Onassis, whose seal of approval made the island of Mykonos a must-visit summer destination from the 1960s onwards. Today, the island is quite popular and remains broad-minded, attracting A-listers and the wealthy jet set for whom Mykonos is the Staint-Tropez of the eastern Mediterranean. The best times to visit are June and September, when it is busy enough to experience the island’s “boho” vibe, but not too crowded.
Discover @ Mykonos Old Town
As the sun sets over the horizon, an impressive hubbub fills the maze of alleyways throughout Mykonos Old Town (also known as Chora). Throughout the summer the outdoor Anemo Theatre, located in a large garden overlooking the town, hosts concerts and performances.
Shop @ Luisa Beach on Psarou Beach
Following a late lunch at Nammos, head to the boutique Luisa Beach. It offers eclectic beachwear from both local and international brands. Pick up a matching kaftan and bikini to wear with locally-made Greek sandals. The shop also has a second boutique in Mykonos Town; it carries men’s clothing and accessories. Soho-Soho is another designer boutique with boho-chic island attire for both men and women. Finish off the look with a stunning piece of jewelry from Kessaris. For Italian design, Bollicine is in an old Mykonian bakery. This chic boutique offers an abundance of aperitifs, cocktails and champagnes to accompany the fine wares for sale. An area within the boutique showcases exclusive collaborations with artists and designers.
Explore @ Dragonisi
Dragonisi is a tiny islet lying just off the south coast. The perfect anchorage for swimming and exploring, certain times of year the beautiful caves also are a breeding ground for rare monk seals. Those looking for a little watersports action should head to the less-developed northern shore where the winds make for ideal windsurfing conditions.
Dine @ Aegean Poets and The Plate
This sophisticated island is famous for its hip bars and restaurants. Sip an ouzo in the cafés that line the colorful harbor of Mykonos (also known as Hora), or visit Mykonos Town where you will find some seriously good restaurants nestled among the alleyways. For a hedonistic long lunch head to Nammos on Psarou Beach — the Greek alternative to Le Club 55 in St Tropez. Your sedentary long lunch will no doubt segue into dancing on the tables late into the afternoon. Alternatively, Scorpios is a restaurant/ beach club with a chill vibe. Flanked by two bays (Kavos and Paraga) the driftwood day beds and soul-jazz tunes make for one of the best beach clubs in the Mediterranean.
Seafood lovers should take the tender to tie up alongside Spilia at Kalafatis Beach. Tucked in a cave-like cove literally on the water, live urchins and lobsters are plucked straight from a saltwater pool right in front of you, bringing a new meaning to the word fresh. Try the famous lobster and sea urchin pasta. Sip cocktails at Caprice while the DJ spins to the setting sun. Follow on with dinner and a party at Sea Satin. This restaurant is set under the windmills; request a table by the water’s edge.
Another restaurant that should be high on your list for dinner ashore is Aegean Poets at Mykonos Blu. Located above Psarou Bay, the restaurant is a refuge away from the nightlife of Mykonos Harbor. For those looking for a party, the Design Hotel Mykonos Theoxenia is one of the island’s hippest hotels and plays host to The Plate restaurant. Overlooking the waterfront, the menu is full of some of the best Mediterranean dishes on the island.
Spa @ Royal Myconian Resort & Thalasso Spa
If you can fit in a detox day, or simply fancy a treatment ashore, head for the Royal Myconian Resort & Thalasso Spa. Its unique treatment program uses mineral enriched seawater, known for its curative and restorative effect. Alternatively, for a daily dose of yoga, make your way to Scorpios. Get there early for morning yoga before spending the day flitting between the restaurant and beach (sumptuous beach beds included).
Anchor @ Ornos Bay
Situated southwest on the island, Ornos Bay is one of the most popular anchorages as it’s sheltered from the Meltemi (the strong, dry north winds of the Aegean). Take the tender ashore to some of the best beaches along the south coast. For parties, head to Paradise Beach; for a quieter affair, head to Platis Gialos. Alternatively, Buddha-Bar Beach at the Santa Marina resort is located right in Ornos Bay. Glamorous yet relaxed, ask for a table overlooking the ocean and enjoy Asian fusion at its best.
Despite being one of the most popular of the Cyclades archipelago, the quintessential Greek isle of Santorini is a haven of peace and tranquility. Born of fire and brimstone, the vertiginous, crescent-shaped island is perched on the edge of a volcano. Best known for spectacular sunset views over the calderas, sheer cliffs capped by hilltop towns frame the deep harbor where the daily activity of ships and yachts provides the island with thousands of visitors every summer. You’ll want to be on deck for the spectacular arrival into the Port.
Go ashore @ Oia
Catch the famous Santorini sunset at Oia. The ultimate Greek island village is made up of white houses and domed churches perched over the lip of the caldera.
Be seen @ Hasapiko
Housed in a former butcher’s shop in Oia, the lively bar at Hasapiko has become an island institution.
Dine @ Homeric Poems
Santorini is better known for its cocktail and dining scene, more than for nightlife. Many of the best restaurants are conveniently located in the island’s top hotels. Homeric Poems is one such establishment. It offers a cluster of stylish villas and its restaurant, which sits on the edge of the Firostefani cliff, provides spectacular views over the caldera. Further, heart-stopping views can be found at the restaurant at Santorini Grace. Mediterranean-fusion cuisine is best enjoyed on the cliff-top terrace, the perfect vantage point from which to enjoy the famed sunsets. There also is a private candlelit cave for special romantic occasions.
The Alati Restaurant at the Vedema Resort is found in a converted 400-year-old winery cave; the perfect setting for tasting vintages grown in the surrounding vineyards. Choose from indoor or terrace dining; both showcase the spot’s creative seafood cuisine. There also is a private dining room in a secluded area of the cellar; the Canava Wine Bar is situated in the catacomb of the winery.
Shop @ Fira
Take the cable car to Fira and walk the cobbled streets where you will find several designer boutiques. Odos Ipapantis (Gold Street) is lined with jewelry shops. Oia also boasts many jewelry stores, but is better known for its contemporary art galleries.
Culture @ Akrotiri
One of the most important archaeological sites in the Aegean, the town of Akrotiri was destroyed by a volcano in the 17th century BC, but is miraculously preserved under layers of lava. The Pompeii of the eastern Mediterranean, the town was one of the most significant settlements in its day; when visiting, you’ll see that the buildings and their contents remain.
Anchor @ Thirassia, Palea and Nea Kameni
The satellite islands of Thirassia, Palea and Nea Kameni are known for their superior beaches.
Less crowded than its famous neighbor Mykonos, Paros is one of the most enchanting of the Cyclades islands. The surrounding waters are ideal for all manner of water sports — they’re particularly well known for favorable windsurfing conditions. The main port and island capital Parikia can, on first impression, seem rather disappointing, but step behind the seafront and you will find cobbled streets and a pretty town.
Be seen @ Naousa
The island offers respite in the fishing haven of Naousa in the north of the island. A quaint fishing village by day, the sunset transforms the bay into a vibrant social scene, with restaurants and tavernas frequented by visitors and locals alike.
Culture @ Parikia
Paros is not famed for its antiquity but go ashore at Parikia and you can discover the Byzantine Ekatontapiliani, otherwise known as the Church of 100 Doors.
Step ashore @ Chrissi Akti
There are dozens of great beaches dotting the coastline. Chrissi Akti (also known as Golden Beach) on the southeast coast is a stretch of golden sand, just shy of a mile, backed by tavernas. It has an offshore wind and so, like many of the beaches on Paros, is a popular spot for windsurfing. Santa Maria is another famed beach with clear water and shallow sand dunes.
Anchor @ Kolimbithres
Divided by smooth giant rocks, Kolimbithres is probably the prettiest beach on the island.
Naxos is the largest island in the Cyclades archipelago, yet is lesser known. Adorned with small coves, countless chapels and hundreds of churches, most of which are Byzantine, the island is perfect for those wishing to step ashore and explore.
Culture @ Chora
In the capital of Chora you will find a Venetian castle and a variety of mansions built by the Venetians between the 12th and 16th centuries. The village of Apiranthos also boasts Venetian architecture and a Venetian tower crowns the marble-paved streets.
Anchor @ Kastraki
At just less than five-miles long, the beach at Kastraki has won awards for its clean sand and clear waters. The coastline is brimming with some of the longest sandy beaches in the Cyclades. For great windsurfing conditions, head to Ayois Yeoryios. The most popular of the island’s beaches, it can be crowded during the peak season as Athenians in the know flock in, but it’s ideal for those looking for watersports action.