Where to stay in Cephalonia: Overlooking Fiskardo, Emelisse is a resort hotel with a great little Elemis spa. For mind-blowing views and ultra-chic interiors, check into Villa Althea, available through Beyond Spaces. . Blissfully isolated, Fiskardo Cottages are a pair of stone houses brimming with art and antiques. Footpaths through the woods lead to quiet bays. For fancier villas, try Five Star Greece.
Tinos is only 15 minutes from Mykonos, so it's a wonder it isn't overrun with tourists. The harbour is swarmed on 15 August, however, when Orthodox pilgrims flock here to kiss the icons at Panagia Evangelistria monastery, one of the holiest sites in Greece. Otherwise, the island is miraculously untouched. Solitary chapels and whimsical dovecotes stud thyme-scented hills, dropping to sandy bays whipped by the meltemi wind. There's a nascent surfer scene on Kolibithra bay, where a VW camper van has been converted into a cute beach bar.
Apart from a boat trip to the smouldering crater of Nea Kameni and hot springs at Palia Kameni, there's not much to do but gaze at the mesmerising views from your suite, dangling on the edge of the caldera. The best hotels in Santorini are concentrated in Oia, but the inland village of Pyrgos is up-and-coming. Go for a twilight Bellini at Franco's or a cocktail at newcomer Botargo, with views that will leave you light-headed, followed by dinner at Selene, a pioneer of new Cycladic cuisine.
Christened the Garden Island, Kauai’s splendor extends from its vermillion Waimea Canyon, plunging down 3,600 feet, to its rugged Napali Cliffs, stretching up 4,000 feet. Often dotted with dozing monk seals, Kauai’s Poipu Beach has appeared on Dr. Beach’s esteemed list of America’s Best Beaches. Rivers, rainforests and waterfalls garnish the interior; don’t miss a photo op of Wailua Falls, famously featured in the opening credits of Fantasy Island, which aired from 1977 to 1984.
The mountainous interior, all sleepy stone villages poking out of pine forests, is great for hikes and bikes. (Eco Zante can arrange outdoor activities guided by insiders.) Askos Stone Park is a wildlife sanctuary inhabited by deer, chinchilla, and dozens of other species. After exploring the Venetian castle high above the harbour, treat the kids to thin-crust pizzas (with grown-up toppings like bresaola, aubergine, and gorgonzola) at Alesta on cute St Mark's Square.
Argostoli is the capital on the mid-west flank of the island and is not really a destination itself, that moniker falling to the contiguous beach scene running from Lourdata south eastward to Skala. While development might have caught up here by now, it should still be a pleasant beach scene and focus for a relaxing stay. The Melissani Cave on the east coast is a must attraction and while it can be visited on a day excursion from anywhere on Kefallonia the two villages or Agia Efthymia and Poros are low-key ‘resorts’ pulling in a regular crowd of travellers and may warrant a look-in. The port of Pesada (just west of Lourdata) is the home of the local ferry to Zakynthos (Zante).
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Beach Day: Spend a day on one of many beautiful small beaches and bays, including pebble and sand beaches. Beaches to check out are Pocukmarak (the biggest beach on the south side, which also happens to contain a stone sarcophagus and two covers in the water that are around 1500 years old), Tratica, Carpusina and Sotorisce (the biggest and the most popular beach on Silba).
Where to stay in Crete: A 300-year-old hamlet surrounded by olive groves, Kapsaliana Village Hotel exudes peaceful authenticity. On a sandy bay just beyond Chania, Ammos Hotel smartly combines Scandi chic with a child-friendly vibe. Blue Palace Resort & Spa beats the (stiff) competition in Elounda with its spiral stone Isola Beach Club, thalassotherapy spa, and boat trips to Spinalonga island, a national monument just across Mirabello Bay.