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Island-Hopping: Cyclades to Crete

There is no bad itinerary for the Greek islands. Whether you choose the Sporades, the Dodecanese, or any of those other getaways floating in the Aegean, the leading isles in Greece differ remarkably, and they are all beautiful. But the needle flies off the beauty-measuring gauge when it comes to the Cyclades. It might be possible to "see" any of these famous islands in a day: the "must-see" sights—monasteries or ancient temples—are often few. Still, it is best to take a slower pace and enjoy a sumptuous, idyllic 14-day tour. Planning the details of this trip depends on your sense of inclusiveness, your restlessness, your energy, and your ability to accommodate changing boat schedules. Just be warned: the danger of sailing through the Cyclades is that you will never want to leave them. From these suggested landfalls, some of the most justly famous, you can set off to find other idyllic retreats on your own.

Days 1–2: Mykonos

Jewel of the Cyclades, this island manages to retain its seductive charm. Spend the first day and evening enjoying appealing Mykonos town, where a maze of beautiful streets is lined with shops, bars, restaurants, and discos; spend time on one of the splendid beaches; and, if you want to indulge in some hedonism, partake of the wild nightlife. The next morning take the local boat to nearby Delos for one of the great classical sites in the Aegean. Mykonos is one of the main transport hubs of the Greek islands, with many ferries, boats, and planes connecting to Athens and its port of Piraeus.

Days 3–4: Naxos

Sail south to Naxos—easily done in summer, harder in other seasons. Plan on arriving from Mykonos in the late afternoon or evening, and begin with a pre-dinner stroll around Naxos town, visiting the Portara (an ancient landmark), the castle, and other sights in the old quarter. The next morning, visit the Archaeological Museum; then drive through the island’s mountainous center for spectacular views. Along the way, visit such sights as the Panayia Drosiani, a church near Moni noted for 7th-century frescoes; the marble-paved village of Apeiranthos; and the Temple of Demeter. If you have time, stop for a swim at one of the beaches facing Paros, say Mikri Vigla.

Days 5–7: Paros

Go west, young man, to Paros, where the large spaces provide peace and quiet. Paros town has delights profane—buzzing bars—and sacred, such as the legendary Hundred Doors Church. But the highlight will be a meal in the impossibly pretty little fishing harbor of Naousa or, on a morning drive around the island, a visit to the lovely mountain village of Lefkes. Then spend an extra night of magic on the neighboring isle of Antiparos, where off-duty Hollywood celebs bliss out with all the white sands, pink bougainvillea, and blue seas.

Days 8–9: Folegandros

This smaller isle is not only beautiful but, rarer in these parts, authentic. It boasts one of the most stunning Chora towns; deliberately downplayed touristic development; several good beaches; quiet evenings; traditional local food; and respectful visitors. The high point, literally and figuratively, is the siting of the main town—on a towering cliff over the sea, its perch almost rivals that of Santorini.

By Public Transportation

High-speed catamarans have halved travel time between Piraeus and Santorini.

In summer, when ferries and boats run frequently, you should have little trouble moving from any of these islands to another.

All islands are served by air as well as by boat.

Days 10–12: Santorini

Take a ferry from Folegandros south to the spectacle of all spectacles. Yes, in summer the crowds will remind you of the running of the bulls in Pamplona but even they won’t stop you from gasping at the vistas, the seaside cliffs, and stunning Cycladic cubist architecture. Once you’ve settled in, have a sunset drink on a terrace overlooking the volcanic caldera. You can also find many view-providing watering holes in Fira, the capital, or Ia, Greece’s most-photographed village. The next day, visit the Museum of Prehistoric Thera; then enjoy a third day just swimming one of the black-sand beaches at Kamari or Perissa.

Days 13–14: Crete

Despite the attractions of sea and mountains, it is still the mystery surrounding Europe’s first civilization and empire that draws many travelers to Crete. Like them, you can discover stunning testimony to the island’s mysterious Minoan civilization, particularly at the legendary Palace of Knossos. Along these shores are blissful beaches as well as the enchanting Venetian-Turkish city of Hania. From Heraklion, Crete’s main port, there are frequent flights and ferries back to Piraeus. Athens, and reality.

Updated: 01-2014

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