Lord Byron was on to something when he waxed lyrical about the Greek islands. But with more than 200 to choose from, which ones are the very best Greek islands? Here regular isle-hopper Rachel Howard reveals the ones to get in a speedboat for in 2020.

1. Syros

Best Greek island for: Culture and off-season cachet

On Syros, capital of the Cyclades, you won’t find sugar-cube villages and whitewashed lanes. The colourful 19th-century city of Ermoupoli is built on twin peaks – one Orthodox, the other Catholic, the heritage of a long Venetian occupation. There’s still a strong Italian flavour in Ermoupoli’s marble piazzas, princely mansions, and miniature replica of La Scala, the showpiece of a year-round cultural scene. Syros hosts festivals of animation, dance, digital art, film, classical music, jazz and rembetiko, the Greek blues popularised by local musician Markos Vamvakaris. A few rembetiko joints have survived in the upper town, Ano Syra.

Once Greece’s ship-building centre, Syros still has a boatyard at Neorio. But the most splendid legacy of the shipping industry are the manor houses in Vaporia and Poseidonia. The beaches are slightly less splendid — with the exception of Delfini, Varvarousa, and Aetos in the wild north. But fabulous seaside tavernas abound: Ambela for fresh fish; CIliovassilemar on Galissas beach for samphire and sea-urchin salad and rockfish soup; Allou Yallou in the pretty seaside village of Kini for lobster with orzo. In Ermoupoli, the finest places to eat and drink are along Androu Street: Ousyra, where the chef plates up Greek-ified pasta and beautifully balanced salads, and Django Gelato, where the smoked-hazelnut ice cream and fig sorbet sell out in 30 minutes flat. Perhaps the prettiest restaurant of all is Mazi) a vine-covered courtyard festooned with bougainvillaea. Before you leave, stock up on loukoumi (rose-tinted Turkish delight) and San Michalis cheese from Prekas delicatessen, and visit Zylo for hand-made wooden sunglasses.

2. Sifnos


Best for: Big, fat Greek feasts

Sifnos owes its foodie reputation to its most famous descendant, Nicholas Tselementes, who wrote the first Greek cookbook in 1910. Forget souvlaki and moussaka: here, chickpea croquettes and stewed capers are taverna staples. The island is peppered with potteries that produce the earthenware casseroles used for revitháda (baked chickpeas) and mastello (lamb with red wine and dill). Traditional dishes are slow-roasted in a wood-fired oven at To Meraki tou Manoli, a local institution on sheltered Vathy bay. (While you’re there, invest in some timeless tableware from Atsonios pottery, in business since 1870.) In postcard-pretty Artemonas, all roads lead to Theodorou, purveyors of nougat wafers and almond sweets since 1933. You can eat in your bikini at Omega 3, where locally foraged and fished ingredients are given an exotic twist: baby-calamari tempura, smoked eel in chilled melon soup with wasabi, and chickpea sorbet with wild apricot jam and pine nuts. In 2020, Omega 3’s energetic head chef Giorgos Samoilis opened Cantina, an equally experimental taverna in Seralia, a pretty little bay below the beautiful medieval village of Kastro. Lobsters are plucked straight from the sea at Heronissos, then served with spaghetti on the jetty. It's just the right balance of low-key luxury and unspoiled authenticity. Rather like Sifnos itself.

3. Hydra

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. Musicians of all stripes rehearse and record at the (Old Carpet Factory), an 18th-century residence whose double-height ceilings and underground cistern have incredible acoustics.

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.

4. Milos

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 white 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.

5. Serifos

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 Hora, 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 Stou Stratou, 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.

6. Amorgos


Best Greek island for: Deep-blue seas and wide-open spaces

It’s not easy to get to Amorgos. In high winds, the fast ferries stay grounded and the slow boat takes upwards of eight hours from Athens. When you disembark at Katapola, a sleepy harbour lined with great little fish tavernas (our favourites are Prekas and To Mouragio), a sign announces: 'Welcome to Amorgos. Nobody will find you here.'

That’s just the point. This craggy Cycladic island has always attracted loners, hikers, divers and pilgrims, who shuffle up the cliff face to the Monastery of Hozoviotissa, a sliver of white dangling 300 metres above the sea. The water here is a million shades of blue and so startlingly clear you can see every sea urchin lurking on the rocky shore. Even the sage-scented hiking trails are called Blue Paths, because the sea and sky are visible in all directions.

With a population of under 2,000, the locals are outnumbered by shaggy goats that blend in perfectly with the burnished landscape and hippie vibe. But you don't have to be a recluse to fall for Amorgos. There are plenty of all-day, late-night bars where Amorgos groupies meet, summer after summer: Jazzmin, in Hora, for backgammon and cocktails; Pergalidi in Langada for herbal infusions and jazzy tunes; Seladi in Tholaria, with giddying views and a telescope for stargazing.

7. Paxos

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. For the many British Paxos aficionados, 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 such as Marmari and Kipiadi, or across to Antipaxos, an even smaller island that’s a hit with the yachting set. Paths through vineyards and orchards trickle down to bays with sea so clear it looks retouched.

8. Santorini


Best for: Honeymooners and first-timers

Cooing American and Chinese honeymooners line up to take selfies as the sun sinks behind Santorini's caldera, the flooded volcanic crater. That view may be a romantic cliché, but it still takes your breath away. A volcanic explosion blew out Santorini's heart 3,500 years ago, leaving black-sand beaches, vertiginous cliffs in psychedelic hues, and swirling rumours about Atlantis in its wake. The eruption also preserved the ancient city of Akrotiri under layers of ash, and created fertile ground for exceptional Assyrtiko grapes and Vinsanto wines. (Sample them at Sigalas and Vassaltis wineries, paired with delicate dishes that let the grapes sing.)

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 and Imerovigli, but the inland village of Pyrgos is up-and-coming. Go for a twilight Bellini at Franco's or supper at Botargo, with views that will leave you light-headed. Emborio is a smaller and even prettier village, with a smattering of old-school coffee shops and Airbnbs. For a glimpse of Santorini before the onslaught of cruise ships and Instagrammers, explore the quieter south (but keep your discoveries to yourself).

9. Cephalonia / Kefalonia

Best Greek island for: Laidback family holidays

Casting Penélope Cruz as a Greek peasant is improbable. Shooting a World War II film on an island flattened by an earthquake in 1953 sounds even crazier. And yet Captain Corelli's Mandolin put under-the-radar Kefalonia (Cephalonia) in the spotlight in 2001. The dramatic scenery still lives up to the hype: milky-white Myrtos beach, the island's pin-up; pine-fringed Horgota beach; and the giddying heights of Mount Ainos, a national park where deer and wild horses roam. Outdoor Kefalonia organises four-wheel-drive safaris, if you can't face the hairpin bends. Surprisingly, the two prettiest seaside villages - Assos and Fiskardo - didn't make the cut. But the yachting set has discovered their photogenic charm. Everyone from John Galliano to Jon Bon Jovi has jumped ashore to taste the seafood pasta at Tassia in Fiskardo, washed down with local Robola and Muscat wines. (We recommend the organic muscat from the 19th century Haritatos Estate in Lixouri, also an enchanting setting for wine tasting.) The rocky coastline around Fiskardo is deliciously pristine: go snorkelling at tiny Dafnoudi or Emblissi, flanked by slabs of limestone that turn the water electric blue.

10. Corfu

Best of the Greek islands for: character and lush landscapes

Corfu is the It Girl of the Ionian islands. The cosmopolitan capital is a charming clash of Venetian, British and French colonial influences. Evenings kick off with cocktails on the Liston (a colonnade modelled on Paris's rue de Rivoli), followed by dinner at Salto, an unpretentious wine bar and bistro on the edge of the Old Town.

With its pastel villages, rolling olive groves and grand manor houses, the rest of the island recalls Tuscany - but with some of the best beaches in Europe. The smart set stay on Corfu's north-east coast (nicknamed Kensington-on-Sea) where the Rothschilds like to unwind. It's wall-to-wall Sloanes and speedboats at Agni, a tiny fishing village with three rival tavernas (Toula's is the best). From here, you can rent a boat and putter to your own cove: perhaps Nissaki, Agios Stefanos or Kerasia. These idyllic bays still resemble the 'delectable landscape' that Lawrence Durrell fell for in the 1930s — now back in vogue thanks to the ITV series, The Durrells. Or venture inland to Ambelonas, an enchanting winery, restaurant and cooking school that specialises in unusual local dishes, such as roast pork with quince and crème brûlée with Corfiot kumquats. Steer clear of the south, especially Kavos. Unless you happen to like wet T-shirt contests.