1. 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. Most places to stay 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).
Where to stay in Santorini: Trendier pretenders come and go, but Perivolas is still the most stylish and peaceful place to stay. If you have the cash to splash, and can’t stand the crowds, take over Perivolas Hideaway, a waterfront villa on Santorini’s undiscovered offshoot, Thirassia, or Erosantorini, a stunning clifftop estate with a tiered pool plunging 1,000 feet to the sea. The collection of suites at The Vasilicos, the former summer house of a larger-than-life art collector, still feels very much like home, due to charming staff and effortlessly classy interiors. For a villa stay, we like Eolia Superior Villa for its communal living space, quirky archways and glistening blue sea views. You can also find unique Cycladic homes to rent on Airbnb, including this incredible cave house in Oia. For more, see our edit of the best hotels in Santorini.
2. 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. Read more about Amorgos, Greece.
Where to stay on Amorgos: There are very few hotels on Amorgos, beyond basic rooms to let. Vorina Ktismata is the exception, with seven smart apartments looking out across Hora’s white-washed rooftops.
2. 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 (ousyra.com), 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. For more recommendations, see our insider guide to Syros.
Where to stay on Syros: On the waterfront in Vaporia, Xenon Apollonos has just three bedrooms with stencilled ceilings, period furniture, and the sea framed in floor-to-ceiling windows. Hotel Ploes, a palazzo on the rocks, is the next best thing. We also love Aristide Hotel, an aristocratic and eccentric nine-room hotel set back from the water on a quiet street. For a private stay, the infinity pool at Villa Syros is a knockout, while Villa Lefko if a perfect family pad right on the beach.
4. Naxos
Best for: Endless sandy beaches
Naxiots once made considerable fortunes exporting potatoes, cheese, marble and emery. Locals bequeathed undesirable seaside plots – useless for farming – to their laziest offspring. When tourists cottoned on to the island’s scores of fabulous beaches, these wastrels found themselves sitting on gold mines. The west coast of Naxos is fringed with mile upon mile of powdery sands. Agios Prokopios and Agia Anna delight toddlers and teenagers alike with their shallow waters and beach bars. As you head south, the beaches get wilder: Plaka, where you can gallop across the dunes on horseback, Mikri Vigla for windsurfing and kitesurfing, and crystal-clear Kastraki.
Should you tire of frolicking on the shore, three supersized kouros statues are hidden in the hills and there are dozens of drowsy villages to explore. Try kitron, the local citron liqueur, at the Vallindras distillery in Halki or sample homemade wine and arseniko cheese under the plane trees in Ano Potamia village. No wonder Herodotus described Naxos as ‘the happiest of islands’.
Where to stay in Naxos: Corona Borealis is a seven-suite retreat with a pool poised for sunset and a private cove where you can have supper under the stars. Kavos is a low-key complex of boxy white villas, set among bright bursts of bougainvillaea, geraniums, and roses, above Agios Prokopios beach. Adults-only Naxian on the Beach is just a few sandy steps from the sea on Plaka beach. The 10 rooms are decked out in bamboo, wicker and weathered wood, and the restaurant, Tortuga, pulls in honey-toned locals for its contemporary comfort food and beach-shack vibes. On Airbnb, this modern Cycladic home near Naxos town has a huge private outdoor space with a barbeque, swing and mini-pool.
5. 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 previous energetic head chef Giorgos Samoilis opened Cantina, an equally experimental restaurant 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.
Where to stay in Sifnos: With its cliff-top infinity pool and soft-focus sunsets, Verina Astra is effortlessly sexy. Verina Suites on Platis Gialos beach is more family-friendly. Kamaroti is an effortless crowd-pleaser with its green lap pool shaded by olive trees, mid-century modern touches, and deliciously unpretentious Greco-Spanish menu. Sifnos House, a boxy little number overlooking the low-key port of Kamares, is steps from a sandy beach and a charming strip of seaside tavernas. For something unique, Mylolithos House is a charming one-bedroom bolthole set within a windmill built in 1864.
6. 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. See our full guide to Hydra, Greece.
Where to stay in Hydra: Built in 1796, the nine-room Orloff Boutique Hotel oozes old-world charm. If a pool is a priority, take over one of the island’s Airbnbs, such as Anemos, a beachfront villa with heated pool in Porto Cheli.
7. 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.
Where to stay on Serifos: We love Verina Astra, an affordable boutique hotel with incredible views near Artemenos. Chill & Co is a sexy nine-room newcomer on the harbourfront with a great breakfast and cocktail bar. In Hora, The Captain’s House is a beautifully restored 19th-century mansion available on Airbnb.
8. Mykonos
Best of the Greek islands for: Decadent parties and five-star hotels
Mykonos had gay clubs and sunrise parties long before rave culture was even invented. Its bohemian allure hasn’t faded since the 1960s, although the once naked beaches now have nail bars, personal trainers and house music pumping out all hours. The influx of supermodels and superyachts has inspired hot new hotels and restaurants. The hippest place to show off your abs is Scorpios, a louche beach bar that puts Ibiza’s finest in the shade (book a cabana to watch the sunset). After hours, it’s always Astra, where you might find Keith Richards chatting up Karolina Kurkova. The gay crowd has dwindled, but drag queens and oiled bodybuilders make a splash at Jackie O, overlooking Super Paradise bay.
If the glitzy excess gets too much, escape to Fokos taverna for superfood salads and lamb chops, or Kiki’s, an off-grid grill-shack overlooking Agios Sostis bay, where even Naomi Campbell has to queue for a table. Or cruise over to the tiny island of Delos, an archaeological sanctuary that once thronged with 30,000 sun worshippers (the temple is dedicated to Apollo, the Greek god of light).
Where to stay in Mykonos: If you’re here to party, check into Soho Roc House – guests have priority access to Scorpios and the poolside scene is smoking. For something more lowkey, Santa Marina resort tumbles down a private peninsula with a full-blown spa, a secret sandy beach, and a Riva to whisk you off to Nammos or Scorpios, if you can peel yourself off your canopied sunbed. If you prefer to be in the thick of it, try Branco on Platis Gialos beach, or The Belvedere, the gold standard in Hora. For a group stay, takeover the Airbnb Villa Fleur de Sel, a beautifully designed space sleeping 12 with an infinity pool and barbecue. For more recommendations, see our guide to the best hotels in Mykonos.
9. Tinos
Best for: Traditional villages and knockout tavernas
Tinos has more than 50 villages, each vying to be fairest of them all. In Pyrgos, famous for its marble craftsmen, sculpted birds and flowers decorate every doorway. In Volax, basket weavers squat outside cottages carved from giant boulders, seemingly flung from the heavens by Zeus in a fit of pique. There’s even a village called ‘love’, Agapi, where you can tuck into wild-fennel fritters at the only taverna. Tinos takes its food culture seriously: there are artichoke, caper and honey festivals. Marathia launched the island’s farm- (or fishing-boat-) to-table scene, elevating local ingredients into complex modern dishes. For a perfect meal in perfect surroundings, go for cuttlefish risotto and octopus caramelised in grape must at Thalassaki, served on the jetty in Isternia bay, then watch dusk bleed into the horizon from Exomeria bar.
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.
Where to stay in Tinos: Up in the hills, Xinara House is a hidden-away guest-house in a former bishop’s residence, snazzily restored with a magpie mix of traditional mosaics, contemporary art, antique crockery and designer furniture. For an Airbnb stay, The Detailor is a thoughtful modern villa with mellow vibes and views for miles.
10. Folegandros
Best Greek island for: Authenticity with a bohemian buzz
The village square should be your first port of call on any Greek island: settle into your favourite café, pick up local gossip, and adjust to the languid pace of life. On Folegandros, this presents a challenge: the cliff-hanger capital, Hora, has not one but three squares, each brimming with a jumble of cafés, tavernas and dinky raki bars. We recommend (Pounta), where the Danish owner makes (and sells) the lopsided cups and bowls in which your coffee and Greek yogurt are served. From Hora, zigzagging steps lead up, up and away to the only real landmark, Panagia church; make the pilgrimage at sunrise (perhaps after an all-nighter at dimunitive Astarti bar).
Folegandros – which means ‘iron hard’ in ancient Greek – is as barren as its name suggests. Fruit trees are protected from fierce winds by rings of stones. You won’t find sandy beaches lined with sunbeds; only limpid, pebbly coves, such as Katergo, Ambeli and Livadaki. Set in the rocks above Agios Nikolaos bay, Papalagi serves big fat prawns and whole grilled octopus on a wooden deck aligned with the horizon. Water taxis service some beaches in high season; otherwise you’ll have to scramble down rocky footpaths to cool off. On your way home, stop at Mimis or Synantisi in Ano Meria for the island speciality of matsata (goat or rabbit stew with hand-made pasta).
Where to stay on Folegandros: Midway between the port and town, Anemi has a fresh, witty design and is ideal for families and fitness freaks, with a yoga studio in the vineyard. Simple and spare, Anemomilos is all about the staggering views. The helpful Patelis family and cliff-edge bar are among the hotel’s unpretentious charms. Blue Sand hotel hovers on the hillside above Agali beach; space and privacy are a little limited, but those views and steps leading straight to the water make up for it. On Airbnb, we like the look of Maistros, a spacious apartment with a private terrace that overlooks the Aegean.
