An A-Z of Greek islands – and how to plan the perfect holiday

If I had a drachma for every time someone asked me which Greek island to visit, I’d be as rich as Midas (hopefully without the donkey ears). Finding the perfect Greek island for friends (or even strangers – I receive many unsolicited emails requesting advice) is like matchmaking: it doesn’t always work; but when you get it right, it’s love at first sight. It might even spark a life-long romance. But how can you choose just one island, when all are lovely in their own idiosyncratic way?

I would describe my own relationship to the Greek islands as polyamorous. There are islands I can’t get enough of, like Skyros, Tinos, and Sifnos. Others I rely on for quick thrills: Aegina, Hydra and Kea, only an hour or two from Athens. There are the youthful summer flings, like Anafi and Koufonisi, that I don’t dare revisit in case they have lost their lustre. And then there are the islands that have eluded me, like unrequited lovers — best laid plans scuppered by sudden gales, ferry strikes, or just the overwhelming urge to miss the boat, rather than travel onwards to the next island.

Over the years, I’ve stayed in super-swanky resorts on Mykonos, cliffhanging villas on Santorini, and shipowner’s mansions on Syros. I’ve had the run of a private island off the coast of Evia. But the memories imprinted in my psyche are not the Greece of holiday brochures and airbrushed Instagrammers. They are the moments of quiet communion with the landscapes, people, and rituals of these small, intense worlds. I’ve slept in the clouds at an abandoned monastery on Anafi; travelled to a church festival in the back of a tractor on Rinia; pressed grapes with my bare feet in the highlands of Crete; had raki shots and prickly pears for breakfast in a shepherd’s hut on Amorgos.

Rather than working my way around the archipelago from Andros to Zakythnos, I’ll let the winds and gods plot my course. But for those who might find it helpful, here’s my A-Z of Greek islands:

A is for Aegina

Only an hour from Athens, Aegina should be overrun with tourists. Yet this rough-around-the-edges island remains largely undiscovered. “Aegina is definitely not the most beautiful island in Greece, nor the trendy place it was in the Sixties, but it has a unique atmosphere,” says Isabelle Zigliara, who left Paris to set up La Conciergerie d’ Egine. Her portfolio of villas includes the former home and studio of renowned painter Nikos Nikolaou. “A lot of Greek intellectuals used to gather in the garden, gazing at the sea and having conversations until late at night,” says Zigliara. “The three suites have been elegantly restored by Nikolaou’s heirs: the architect Theodore Zoumboulakis and his sister, the gallerist Daphne Zoumboulakis.” The house features drawings by Nikolaou and sculptures by his friend, Yannis Moralis.

Nikolaou Residence (00 30 697 2580 671; nikolaouresidence.gr) from €70 in low season.

B is for Beaches

From rolling sand dunes to remote pebble coves, echoing sea caves to thumping bay-side bars, the Greek islands have beaches for every mood. The powdery white sands of Lefkada and Zakynthos have legions of fans, but my money is on Amorgos. This far-flung Cycladic isle has the clearest water, the fewest crowds, and the widest horizons. No wonder Luc Besson shot The Big Blue here.

It’s a seven-to-nine hour ferry journey from Athens to Amorgos (Check openseas.gr for schedules). No-frills Minoa Hotel (0030 22850 71480; hotelminoa.gr) is well-placed on Katapola waterfront; doubles from €45. Vorina Ktismata (00 30 22850 71580; vorinaktismata.com) in Chora is more upmarket; doubles from €145.

C is for Chios

“Chios is an island of unique character – taking in a bloody history, 20 medieval fortified villages, a Unesco-listed monastery, and good walking opportunities,” says Dudley der Parthog, Sunvil’s Greece Director. “Given that the island possesses such variety, it remains remarkably little known.” Perhaps the local shipowners – who made their fortunes trading in the mastic resin that grows exclusively on Chios – prefer to keep this large, rugged island to themselves.

A seven-night stay at the characterful Kyma Hotel in Chios town costs from €987pp (two sharing), including flights, B&B, and transfers. (020 8758 4758; sunvil.co.uk)

D is for Despotiko

When Despotiko’s sole inhabitant, a shepherd, spotted a Byzantine coin in his dusty goat pen, he didn’t realise how momentous that discovery would be. When archaeologists investigated, they uncovered several marble columns, fragments of archaic statues and hundreds of shards inscribed with the word ‘Apollo’. It turns out Despotiko, a tiny island between Paros and Antiparos, was one of the most important sanctuaries in antiquity. A few minutes’ boat ride from Agios Georgios beach on Antiparos, Despotiko is as awe-inspiring as Delos, without the jostling day-trippers from Mykonos.

Captain George ‘Sargos’ Marianos (00 30 697 3794876; sargosantiparos.gr) offers boat trips around Despotiko on his wooden kaiki. 

E is for Elafonisos  

Adrift off the eastern tip of the Peloponnese, tiny Elafonisos could be in the Caribbean rather than the Aegean. The sandy beaches are as fine as flour, the sea palest turquoise. But instead of palm trees swaying in the breeze, there are cedars and sand lilies; instead of swimming with tropical fish, you can snorkel over the submerged Bronze Age city of Pavlopetri. The twin bays of Simos are the most photogenic, but can become very crowded.

Elafonisos is a nine-minute, ferry ride from Pounta, in the Peloponnese. Accommodation on the island is basic. Instead, check into Kinsterna (00 30 27320 66300, kinsternahotel.gr), a Byzantine manor house that’s a 45-minute drive from Pounta. Doubles from €198.

F is for Folegandros

Is this the quintessential Cycladic island? Sugar-cube village, clifftop monastery, luminous bays only accessible by boat or vertiginous dirt tracks — check, check, check. Folegandros is no longer the hippy hideaway it once was, but it still has enough rustic charm and barefoot insouciance to be quietly, intensely cool.

Fly to Santorini then take the high-speed ferry (seajets.gr) to Folegandros. Family-run Anemomilos (00 30 22860 41309; anemomiloshotel.com) has stylish studios dangling on a cliff-edge, from €230.

G is for Gorges

You could have a perfectly lazy beach holiday on Crete, but the island’s true nature is hidden in its spectacular gorges. Samaria is the most famous, but there are dozens of less challenging options. Maria Mylonaki, of Crete specialists Diktynna Travel, recommends the Aradena Gorge, which begins at an abandoned village and ends with a swim in the Libyan Sea; Agia Irini, shaded by ancient olive trees; or Zakros, whose caves contained Minoan tombs. “The canyons resemble the Cretan character: rugged, rough, to be approached with caution, but always generous and by no means boring,” says Mylonaki.

Diktynna Travel’s (00 30 28210 41458; diktynna-travel.gr) walking guides are not just wilderness and wildlife experts. They will unlock chapels covered in frescoes and pre-order fish soup at the best taverna.  

H is for Hydra

“Ouzo, intrigue, and Leonard Cohen,” is how one review described A Theatre for Dreamers, Polly Samson’s novel about an ingenue’s coming of age in the bohemian swirl of 1960s Hydra. The heady, languorous isle hasn’t changed that much since then: its architectural integrity is intact, motorised vehicles are still banned, and courtyard tavernas draped in jasmine still thrum with artists, writers and muses. Yes, it’s craggy, costly, and has barely any beaches; but Hydra’s allure remains irresistible.

Bring the gang and shack up at Kamini House, (00 30 6932906377; hipawayvillas.com), the picture of blue-and-white perfection, with terraces shaded by exuberant bougainvillea. From €800 per night, sleeps 8.

I is for Ionian Islands

“A love affair between romantic Britons and the Ionian islands has been going on for 200 years,” says Ileana von Hirsch, a native of Ithaca and founder of luxury villa agency Five Star Greece. “The islands were part of the British Empire for 40 years. Edward Lear painted the Corfu landscape and Lord Byron was offered the crown of Ithaca by the locals (sadly he turned it down, but was tempted). The Durrells were following a respected tradition of fleeing Albion’s dank and grimy shores for the clarity of Ionian water, the soft breezes, sultry mountains and shady groves of cypress and olive.”

With commanding views, elegant interiors, and access to a private jetty, Corfu MC is a testament to its Anglo-Greek owners’ fine taste. From €18,000 per week, sleeps 8 (020 8422 4885; fivestargreeece.com).

J is for John of Patmos

Don’t be put off by St John’s visions of fire and brimstone – Patmos is a heavenly revelation. The valleys are speckled with white chapels, the gentle coastline scalloped with naked beaches. All winding roads lead to Chora, the most beautiful village in the Aegean – a blinding white maze huddled around a fortified monastery founded in 1088 AD. Dripping with bejewelled icons and Byzantine treasures, the monastery’s spiritual energy is palpable and profound. To its many disciples – from Orthodox pilgrims to jet-setting fashion editors – Patmos is the Alpha and Omega of Greek islands.

Patmos is an eight-hour ferry ride from Athens. The nearest international airport is five islands away. Scott Williams (01749 812721; scottwilliams.co.uk) has a couple of handsome villas, from €2,900 per week.

K is for Kea

The closest to Athens of all the Cyclades, Kea is a game of two halves. The yacht set flirt over lobster spaghetti in the bays of Vourkari and Koundouros, while purists commune with nature in the oak-clad hills, where sheep huddle around ice-cold springs and farmers till their fields with donkeys. Whatever your island style, don’t miss the incredible (and incredibly remote) ruins of Karthea, with a temple and amphitheatre overlooking a sunken city.

Kea is one hour by ferry from the port of Lavrion. For splendid isolation, hole up at Kathikies (kathikies.gr) two 100-year-old farmhouses on the edge of the world. From €575 per week.

L is for Leros

Sailing into the lake-like harbour of Lakki is a surreal experience. Along the waterfront are monuments to Mussolini’s imperialist aspirations: a 1930s town, with a school, market hall, hotel, and cinema, all built in the rationalist style. The wide boulevards and curvaceous buildings are completely unexpected. The rest of Leros is quiet and unassuming, all sleepy villages, shallow bays, and old-fashioned tavernas with tables in the sand.

Olympic Air (olympicair.com) has regular flights from Athens to Leros. Or fly direct to Kos, Samos or Rhodes and take a ferry from there. Archontiko Angelou (00 30 22470 22749; hotel-angelou-leros.com) a delightful manor house from 1985, has doubles from €89.

M is for Marathi

Population: five. Beaches: one. Cars and shops: none. When the Emilianos family jumped ship at Marathi, a speck in the Dodecanese, in 1977, there was no electricity and no running water. Undeterred, they set up a seaside taverna where everything was fished, grazed and grown locally. Not such a crazy enterprise after all: Pantelis taverna has become a cult stopover for Greek island connoisseurs – particularly those with their own yachts. Don’t have your own boat? Book one of the modest cottages to let.  

Pantelis Taverna (00 30 22470 32609; marathi-island.gr). Various boat companies offer day trips to Marathi from Patmos, Leros, and Lipsi.

N is for 1900

“I’ve been in love with the Mastoridis mansion for years,” says architect Dimitris Zographos, who has masterfully restored many neoclassical mansions on the Dodecanese island of Symi. “A ship’s captain, Mastoridis brought the first diving suit to Symi, a present from the Brits while he was working in the West Indies. It was his wife – a woman in 1862 – who had the courage to try it for the first time in front of all the men, who were reluctant to do so.” This incident changed the fortunes of Symi, which soon developed the world’s largest sponge diving fleet. Zographos has since transformed the magnificent 19th-century mansion into a heritage hotel with just four sea-facing suites steeped in history – painted ceilings, cement tiles, Ottoman closets for minibars, vintage chests as luggage racks.

1900 Hotel (00 30 6944 623284; 1900hotel.com) opened in June 2021. Prices from €190.  

O is for Ouzo

“Lesvos has the best ouzo in the world,” says Vicki Atsikbasis, owner of Little Bird, a charming guesthouse and cafe near the village of Petra. “In Lesvos, they say it’s not about where you drink the ouzo but who you drink it with. We do still have our favourite spots for drinking with wonderful company, such as the quaint Caravan Eatery, located on the beach just below Little Bird, the seaside tavernas at Petra, picturesque Molyvos harbour, and Plomari village, where the best ouzo comes from. Here you will also find a couple of ouzo museums and distilleries to visit.”

Jet2Holidays (jet2holidays.com) flies direct to Lesvos from the UK. One-bed villas at Little Bird (00 30 22530 42217; littlebirdlesvos.com) from €150 a night.

P is for Paxos

“Paxos is a bubble of serenity and stillness in spring,” says Faye Lychnou, co-founder of Friends of Paxos, an association that supports cultural conservation on this sophisticated Ionian island. At the height of tourist season, tiny Paxos teems with stylish Italians and posh Brits. While Bono and Abramovich jostle for mooring space outside the fanciest seafood restaurants, the ancient olive groves scattered with secluded stone houses are deliciously peaceful. Friends of Paxos organises bi-monthly history walks, uncovering traces of the Venetians and British, who tussled over Paxos for about 400 years.

The Thinking Traveller (020 7377 8518; thethinkingtraveller.com) has several charming villas on Paxos. A week at Panayia View costs from €3,524 a week (sleeping 8).  

Q is for Quiet

For absolute privacy and peace, check into The Rooster. Hunkered into the low-slung hills of Antiparos – a tiny island with a sleepily sophisticated scene – this eco-minded retreat overlooks a wild, windswept beach. Nature works its healing magic here. The deliciously wholesome food (much of it sourced from the organic farm), and deeply restorative spa treatments simply accelerate the process. “Listen to the sounds around you,” says Lexi, my radiant young instructor, as we ease into a gentle round of sun salutations at the outdoor shala. A rooster crows right on cue.

Garden-view suites from €610 B&B. (00 30 22844 40900; theroosterantiparos.com) 

R is for Ruins

Santorini has Akrotiri, Mykonos has Delos, Crete has Knossos – three of the most important archaeological sites in Greece. Equally impressive yet barely on the tourist radar, the Sanctuary of the Great Gods on Samothrace is hidden in a wooded ravine. The secret rites performed here were never recorded, as the ancients feared retribution by the Kabiroi, twin demons who could whip up deadly storms. Epic in scale and setting, this mysterious sanctuary can often be enjoyed in absolute solitude.  

Palaiopolis, Samothraki (00 30 25510 41474, open daily 8.30am-4pm)

S is for Sailing

“Happy is the man, I thought, who, before dying, has the good fortune to sail the Aegean sea,” wrote Nikos Kazantzakis in his classic novel, Zorba the Greek. Spetses Cruising offers surprisingly affordable yacht charters, day trips, and water limo services in the Argo-Saronic islands, where the winds are rarely choppy. If you really want to push the boat out, the Alexa J is a single cabin schooner that comes with six crew members. Definitely the most stylish way to island-hop in the Ionian.

Spetses Cruising (spetsescruising.com) operates skippered day cruises for up to 8 passengers from €2,000. Black Tomato (0207 426 9888; blacktomato.com) can arrange a seven-night trip on the Alexa J for £9,500 per night, including flights and full board.

T is for Tsikoudia

Other islanders drink Greek coffee; the Cretans drink shots of fiery tsikoudia. And they will insist that you do too. Lawrence Durrell warned of the consequences of getting carried away by Cretan hospitality: “There are few hazards in such warm-hearted company, but I can think of one. The drink called tsikudi, a kind of local marc or grappa, which has been piously distilled from dragon’s bones, fills one with a strange Byzantine effulgence if drunk by the pailful. The resulting hangover makes you feel like one of those sad, haloed saints in the icons.”

Salis (00 30 28210 43700; salischania.com) has the most extensive Greek wine list on Crete — and a strong tsikoudia game, too.

U is for Underwater Diving

Greece has opened up 91 underwater ship and airplane wrecks to recreational divers. Though predominantly from WW2, some are much older; like the 2,500-year-old Peristera shipwreck, discovered by a fisherman off the coast of Alonissos. The ship’s cargo included around 4,000 amphorae of wine, plus enough crockery for a full-blown symposium. Located in Europe’s largest marine reserve, this “underwater museum” is more like a time machine.

At a depth of around 30m, the Peristera is only accessible to advanced divers accompanied by accredited guides, such as Triton Alonissos Dive Centre (0030 24240 65804; bestdivingingreece.com).

V is for Vaccines

The Greek government has vaccinated the entire populations of islands with fewer than 5,000 residents against Covid in a bid to reassure tourists that these destinations are coronavirus-free. Staff in the tourist industry were given priority.

Kastellorizo was the first Greek island to be declared Covid-free. Mediterraneo (00 30 22460 49007; mediterraneo-megisti.com) has seven waterfront rooms brimming with character. Doubles from €100.

W is for Wind

There’s a reason why the Cyclades are so brutally, beautifully barren. The meltemi, the fierce northerly wind, cools the heat but can whip the mind into an agitated frenzy. Perhaps that’s why Mykonos, the windiest isle of all, has such a wild and restless spirit. According to Ileana von Hirsch, of Five Star Greece: “The meltemi comes in three strengths: kapelata – blows hats off, kareklata – blows chairs over, and trapezata – blows tables over.”

If you’re into windsurfing or kitesurfing, head to Paros or Naxos, where Aeolus will put the wind in your sails.

X is for Xinara House

Peter and Susan Marston stumbled on Tinos by accident — they hopped over from Mykonos while waiting for a delayed flight. “We’d visited lots of Aegean islands, though Tinos, typified in guides as a Greek Lourdes, somehow got missed,” recalls Peter. “We found beautiful landscapes, fields of artichokes, heavenly beaches and excellent tavernas. In a green valley dotted with car-free villages, someone showed us an ancient, dilapidated house once the home of a bishop. It was for sale. Our life suddenly changed – too big to restore for just the two of us, we created a hotel set among quiet terraces.” Filled with contemporary art and design, local marble, mosaics, and antiques, Xinara House is one of the most exceptional guesthouses in Greece.

Prices per night from €145 for 2-3 people (xinarahouse.com). Tinos is easily reached by ferry from Mykonos (15-30 minutes) or Athens (2-4 hours). Both have international airports.

Y is for Yoga

Lithe, lean, and radiant, Anna Martinou and Eranthi Karamali are poster girls for their yoga retreats. “Our retreats draw upon our childhood memories of holidays in the Cyclades. The freedom of the first dive, the sweetness of a salty watermelon, the failed handstands in the sand, and the joy of having nothing more to worry about than your forgotten sunglasses,” says Martinou. As well as open-air classes by renowned yogis, Fykiada retreats celebrate simple pleasures: kayaking through sea caves, hikes to hilltop monasteries, the taste of a real tomato. “We call this ‘the island effect’: people leave our retreats with a straighter spine, a sun-kissed face and a bigger smile.”

Fykiada (fykiada.com) is hosting retreats on Koufonissia and Mykonos from €2,490.

Z is for Zen

Yes, Z is for Zakynthos, the Ionian island that’s shaking off its tawdry reputation with a splurge of adults-only hotels. But for serious zen, head to Serifos where Kaisanji, Greece’s first Buddhist monastery, has now opened. Set among acres of vineyards and olive trees, overlooking the empty sweep of Kalo Ambeli beach, Kaisanji means ‘the temple of mountain and sea’. Slipped into the folds of the landscape, the low stone structure balances Cycladic and Japanese traditions as harmoniously as the temple bells reverberating across the valley. Still the mind and simply be present – the best therapy in these turbulent times.

Yoga retreats are running throughout the year (zencenterathens.com). Suggested contribution is from €450, including classes, accommodation and meals.

Overseas holidays may be subject to restrictions. Check gov.uk before travelling