Greece

Off the southernmost reaches of the Argolis peninsula, the island of Hydra is renowned as a boater’s paradise and a rare car-free destination. Hydra Town rises up the hillsides that surround the u-shaped harbor like an amphitheater, its aquatic stage flanked by cannons. Donkeys are the lone form of transportation up the steep cobblestone lanes, as even scooters and bicycles are banned. The waterfront area is the island’s center for shopping, dining, nightlife and maritime traffic. The town also features art, history and cultural museums housed in converted 18th-century stone mansions.

The sacred and the secular share Patmos, the holy island of the Aegean where St. John is held to have written the Book of Revelation while in exile. Dominating the island, the Monastery of St. John the Theologian is a castle-like complex wrapped by the white-washed buildings of the historic Chora.

Long at the crossroads of power in the Aegean, Ikaria has a historic legacy that ranges from ancient Greeks to the Ottomans. Following 20th-century wars and hardships, the island today is deeply rooted in community and celebration, an ethos said to support the legendary longevity of Ikarians, along with a diet of local fruit, vegetables, honey, olive oil and free-flowing red wine.

Pine-scented Spetses is an upscale and relaxed island that attracts more affluent Athenians than foreign tourists. With its rich seafaring culture, this little island is also hugely popular with the yachting crowd. This is one of the most cosmopolitan destinations in Greece, with beautiful Neoclassical buildings sitting on its fine squares and horse-drawn carriages roaming its pretty streets.

Beautiful beaches, picturesque villages, tranquil churches and local traditions meet Cycladic chic on Sifnos. Long known for its outstanding cuisine – the island was the birthplace of Nikolaos Tselementes, author of the first Greek cookbook – Sifnos is growing increasingly cosmopolitan. The tranquil port of Kamares boasts some fabulous waterfront cafés, restaurants and stores along its long, lovely beach. Visit the exceptionally pretty village of Kástro, a former Venetian citadel that was built on top of an ancient town.

The largest of the Dodecanese islands, Rhodes is renowned for its sunshine, sandy beaches and spectacular heritage. During two centuries of occupation, the crusading Knights Hospitaller transformed Rhodes Town into a medieval stronghold. Today its Old Town is a wonderful tangle of streets and squares that are bustling with cafés and restaurants. The architecture here is fascinating – a beautiful blend Gothic, Byzantine and Ottoman styles.

The bastions of an impressive 16th century fortress stand guard over Rethymno, one of Crete’s most charming cities. The Old Town is wondrously atmospheric, its cobblestone alleyways leading to pretty churches, Italianate palazzos, Ottoman mosques and charming courtyards that are draped in brilliant bougainvillea. Sun worshipers will find Crete’s longest beach, a 12-kilometer stretch of golden sand, just beyond the marina. If you want to escape the bright Cretan sun, some shady municipal gardens and fine museums provide the opportunity to cool down.

Two fortresses – the Ottoman-era Néokástro and medieval Paleokastro – welcome you to the Bay of Navarínou, a natural harbor in the Peloponnese. Established after the 1827 naval battle that paved the way for an independent Greece, Pylos now guards the entrance to this beautiful bay. The area’s many beaches are unspoiled, most notably Voïdhokiliá, a picture-perfect semicircle of white sand that separates the Gialova Lagoon from the sea. A short drive from town takes you to the hilltop ruins of Nestor’s Palace.

One of the most geographically distinctive and culturally rich islands in the Cyclades, Milos is a volcanic island of beautiful beaches, thermal springs and unusual rock formations. Adámantas, the island’s pretty port and nightlife hub, is sheltered inside the volcano’s former caldera. Plaka, the nearby capital, overlooks the entrance to the Gulf of Milos.  This charming hilltop town is home to Plaka Castle with views of the entire island as well as an acclaimed archaeological museum, which features a replica of the island’s most famous find: the Venus of Milo.

Tucked into a forested valley in the western Peloponnese, Olympia was ancient Greece’s center for the worship of Zeus, as well as the birthplace of the original Olympic Games. The Games took place here every four years for over 1,100 years, and the ruins – which include a colossal stadium that was built for 20,000 spectators – are truly impressive. Just 20 miles away on the coast is Katakolon, the maritime gateway to Olympia.