Best Greek island for: Flopping onto a sandy beach with a good book
Skiathos may be the smallest of the Sporades islands, which counts among its number sleepy Alonnisos and the pretty Mamma Mia! location of Skopelos, but it’s by far the most popular, especially with families, who come for the baby powder-soft sandy beaches and laid-back vibe. The island has some of the finest beaches in Greece, with the tree-lined, turquoise-watered Koukounaries in the south the most celebrated and the busiest (forget about getting a sun lounger here in peak season). Those in the north of the island, which can only be accessed by a steep, winding drive through pine groves, are more rugged and windswept but no less idyllic – emerging onto Elia beach, with its crystal-clear sea and rickety wooden taverna, is like stepping into a little slice of paradise.
As dusk falls the town starts to liven up, with most of the action centred around Papadiamantis Street, the main shopping drag. Stroll down it on the way to dinner and browse smart boutiques selling handcrafted jewellery and knick-knacks, or pick up local delicacies from the upmarket Ergon deli, which also has outposts in Athens, Thessaloniki and Mayfair. The buzziest restaurants are clustered around the harbour, with Bourtzi, perched atop a tiny rocky island, the best spot for sundowner cocktails and The Windmill a favourite for elegant suppers. For the most charming setting, head to Sklithri and book one of the taverna’s tables right on the beach. Order an ice-cold Mythos beer, baked feta and a platter of perfectly-chargrilled and out-of-this-world delicious vegetables then watch the sun set over the Aegean, with your toes in the sand.
Best for: Sailors, surfers, and superstar beaches
Lefkada is something of an anomaly. Unlike the other Ionian islands, it’s accessible from the mainland via a causeway on the northern tip. It’s also easily reached from the UK, with direct flights to Preveza, a 40-minute drive. Lefkada’s main town, flattened by an earthquake in the 1950s, won’t take your breath away, but those famous cliff-backed beaches, Egremni and Porto Katsiki, sure will. You’ll find sheltered beaches no matter which way the wind is blowing; but if you’re here for the swell, the south coast is fantastic for windsurfing (head to Vassiliki or Sivota, home to the world windsurfing championships) and Agios Ioannis bay billows with kite-surfers. At Nidri, ignore the unlovely bars and watersports centres, and hop on a boat to explore the little isles nearby. You can swim through sea caves on Kalamos; eat seared tuna with tarama at Errikos taverna on Meganisi, a favourite of reclusive billionaires; and watch the sunset with a basil-infused Mastiha and tonic at Mylos bar, a converted windmill on Kastos.
Want to cool down or escape the summer crowds? Drive through forests of chestnut and pine into Lefkada’s mountainous interior to the somnolent villages of Karya (home to an enchanting textile museum), Eglouvi (to play backgammon under plane trees) and Exanthia (to watch the setting sun from up in the clouds at Rachi restaurant). You might even see paragliders leaping off the mountain.
Best for: The perfect balance of seclusion and sophistication
One of the tiniest Ionian islands, Paxos packs a big punch. Not for its five-star hotels (there are hardly any) or its sandy beaches (practically none), but for its electric blue sea and three dinky harbour towns, each one so pretty it’s impossible to pick a favourite. In laid-back Loggos, on the northeast coast, star-spangled evenings are spent on the waterfront terrace of Taxidi bar, where the owner, Spiros, often jams with local musicians. You could while away days in the waterfront cafés of Lakka, watching lissom sailors hop on and off their yachts.
Protected from the wind but with a lively social scene, the main port of Gaios is characterised by Venetian architecture and a high quota of stylish Italians, who own pale stone villas hidden in the wooded interior or on the crest of the limestone cliffs along the western shoreline. All roads lead to Ben’s Bar, a happy-go-lucky hangout on Monodendri beach, where you can laze under the olive trees with French toast and Piña Coladas. Make sure to rent a motor boat to putter along the coast to pebble coves or across to Antipaxos, an even smaller island rimmed by teal-blue ocean. Paths through vineyards and orchards trickle down to bays with sea so clear it looks retouched.
Best Greek island for: a long weekend with the art crowd
You know when Dakis Joannou, Greece’s foremost art collector, is on Hydra. His yacht, Guilty, is painted in gaudy ‘camouflage’ by Jeff Koons. Every summer, Joannou invites big hitters such as Matthew Barney and David Shrigley to create site-specific installations in the Greek island’s old slaughterhouse. Even the school is commandeered for exhibitions in the summer holidays. Car-free and protected by a preservation order, Hydra has always been the artists’ muse of the Greek Islands. Leonard Cohen set the scene in the 60s; now Brice Marden, Sadie Coles and Juergen Teller have homes here. Athenian artists take up residence at the School of Fine Arts, one of the vast, grey, stone mansions overlooking the horseshoe harbour.
Less than two hours from Athens, Hydra fills up with chic Greeks at weekends. . They come to disconnect and slow down, but also to see and be seen. Wily cats and weary donkeys patrol the back alleys, but all the action happens along the waterfront. Oh look! There’s Olivia Palermo at The Pirate Bar and Chloë Sevigny shaking her tail feather at Hydronetta beach bar. Who cares if there are barely any beaches? You can always find a slab of sun-baked rock from which to leap rock from which to dive into the clearest water in the world.
Best Greek island for: A photogenic and dramatic coastline
Everyone knows the Venus de Milo (which has stood in the Louvre since the 19th century). Until recently, very few had heard of Milos, the volcanic island where Aphrodite’s graceful likeness was discovered. Those in the know jealously guard their treasured island, and especially its 70 (or more) beaches — surely the most diverse and dramatic coastline of all the Greek Islands.
Little by little, though, Milos is being discovered. Instagram is saturated with no-filter shots of the undulating cliffs at Sarakiniko, the bottle-green swimming hole at Papafragas, and colourful, rickety syrmata, tiny boat houses wedged between rock and sea. (You’ll find the best photo opportunities at Klima and Mandrakia). This painterly landscape was shaped by the minerals that have long been a source of wealth – obsidian, alum, barite and sulphur, which still bubbles up in the island’s many hot springs. As the 11,000-year-old mining industry is gradually giving way to tourism, several chic hotels have made an appearance. Go now, before the trickle of visitors turns into a tide.
Best Greek island for: Naturists and purists
The sleeper hit of the Cyclades, Serifos is the summer retreat of interior designers and architects who prefer to keep the sandy beaches to themselves. (One French home-owner is so protective of her hideaway that she tells all her friends she summers on nearby Sifnos.) Even in August, you’ll find coves where you can skinny dip in blissful solitude. That’s because the best beaches (Kalo Ambeli, Vagia, Skala) are only accessible via bone-rattling dirt roads or donkey tracks. Better still, rent a motor boat from the laidback harbour, Livada. Make sure to moor outside Anna’s taverna on Sikamia beach for freshly caught fish and garden-grown salads.
In the cascading hilltop Chora, there’s barely any nightlife, no smart boutiques or fancy hotels. But who cares when you can kick back with fennel pie and raki at Stratos, pick up Natassa Kalogeropoulou’s minimalist ceramics at Kerameio, and listen to Greek folk in the open-air amphitheatre. And all less than three hours from Athens.
Best Greek island for: A mythical retreat for families
Despite its legendary stature, the homeland of Homer’s hero, Odysseus, remains surprisingly under-the-radar. Ithaca’s turquoise and emerald coves are popular with the sailing set, but few visitors venture into the forested hills. So, you might be the only person exploring dramatic hiking trails, like the heady trek to the church of Anogi, covered in 16th-century frescoes (ask for the key at the village coffee shop), or the 8th-century BC ruins of Odysseus’ palace. Do stop at Yefuri (facebook.com/Yefuri) on the way down, for thin pizza, fat chips, and its famous lemon tart.
Yachts moor in the deep, sheltered harbour of Vathy, or Kioni, a miniature port where you’ll find Spavento, the perfect pier-side café-bar. Go any time of day or night for ice-cream sundaes, excellent cocktails, and a soundtrack to make your heart sing. Ideal for low-key family holidays or retreats, rugged little Ithaca is somewhere you can still disappear.
Best for: Castaway coves and a picture-perfect port
Little Symi has the prettiest port in Greece. As you round the headland, neoclassical mansions in every shade of apricot and peach rise like a mirage from the sea. Built by 19th-century sponge and spice merchants, the whole town is now a national monument. You need strong legs to explore – it’s about 500 steps up to the crumbling acropolis – but you won’t need a car. The only proper road peters out at Panormitis monastery, a major pilgrimage site. Ravishing beaches such as Ayios Yorgos Disalonas (backed by monumental cliffs) and Marathounda (where goats will try to filch your picnic) are only accessible by boat or on foot. In the rugged hinterland, more than 100 monasteries are hidden among the pine and cypress forests.
With its laid-back glamour, luminous sea and almost tropical microclimate, Symi is a hit with French and Italian yachties. You’ll find them eating flash-fried baby shrimp, a local specialty, at Tholos, a sensational taverna where the harbour views almost steal the show.
Best for: its cultivation and production of mastic.
This lesser-known isle sits happily in the northeastern part of the Aegean Sea. Chios is most famous for its cultivation and production of mastic, an aromatic resin that forms in teardrop shapes that comes from trees growing in the fertile Mastichochoria region of the island.
Mastic (sometimes known as “Arabic gum,” but not to be confused with “gum Arabic”) has a range of uses, from functional — it’s used in varnishes and paints — to medicinal to edible. On Chios, you can buy mastic-based jams, candies and local liqueurs like brandy ouzo. It’s referred to as a “a tear that pleases, perfumes, relieves and heals.” So you’ll definitely want to stock up on some at the Mastihashop, the island’s main purveyor.The largest mastic village is called Pyrgi. The buildings there are adorned with geometric patterns, called “graffito,” that are like nothing you’ve ever seen.And if that’s not enough, there’s also Nea Moni monastery, a renowned UNESCO world heritage site in the center of the island. A Byzantine monastery, Nea Moni houses treasures such as mosaics and human skulls, among other things. Don’t forget the medieval village of Mesta, built as a maze with tightly spaced homes. The narrow streets were constructed with arches and vaults to protect important buildings from the pirates of the past. The whole place is hauntingly charming.