Greece has over 200 inhabited islands. Each one is different. Each one rewards a different kind of traveller. And yet the question we are asked more than almost any other is simply this: which island should we go to?
After 25 years of crafting bespoke Greek holidays, we have learned that the best answer is rarely about the island itself — it is about you. What you love. How you like to spend your days. What you want to feel when you are there.
So here is our guide. Not a ranking. Not a list of the most popular. Just an honest match between who you are and where you belong.
If you love food...
Go to Crete
Crete is, quite simply, one of the great food destinations of the world. Not just of Greece — of the world. The island has its own distinct culinary identity, shaped by centuries of Venetian, Ottoman and Byzantine influence, and grounded in some of the finest olive oil, cheese, honey and wine you will ever taste.
Eat dakos (barley rusk with tomato and mizithra cheese) at a hillside taverna in the Lasithi Plateau. Drink tsikoudia with a fisherman in Elounda. Spend a morning at Chania's covered market, where the stalls overflow with herbs, olives and mountain greens. Take a cooking class in a Cretan farmhouse and come home knowing how to make stifado properly.
Crete also rewards the adventurous eater. The island's interior — the gorges, the mountain villages, the monasteries — is where the most authentic food lives. We always recommend at least two nights away from the coast.
If you love glamour...
Go to Mykonos
There is nowhere quite like Mykonos. The windmills, the bougainvillea, the impossibly white lanes of Little Venice, the beach clubs that somehow manage to feel both effortless and electric. Mykonos is unapologetically glamorous, and it does not pretend otherwise.
The island attracts a sophisticated international crowd, and the hospitality has risen to meet them. The best hotels here — the Belvedere, the Myconian Collection, the Santa Marina — are genuinely world-class. The restaurants are excellent. The shopping is superb.
Go in June or early September if you want the glamour without the July and August intensity. Mykonos in the shoulder season is a different, quieter, arguably more beautiful place — but the style remains.
If you love romance...
Go to Santorini
We know. Everyone says Santorini. But there is a reason, and it is not just the photographs.
Santorini is the only place in Greece — perhaps in the world — where the landscape itself feels like a love letter. The caldera, formed by one of history's greatest volcanic eruptions, creates a natural amphitheatre of extraordinary drama. The sunsets at Oia are genuinely, breathtakingly beautiful. The cave hotels carved into the cliff face are among the most intimate places to stay anywhere in the Mediterranean.
The trick with Santorini is knowing where to go and when. Oia and Fira in August can feel overwhelming. But Imerovigli, Pyrgos, the southern tip near Akrotiri — these are quieter, more personal, and just as beautiful. We always build Santorini itineraries that take you beyond the obvious.
If you love authenticity...
Go to Symi
Symi is, for many of our clients, the discovery that changes everything. A small Dodecanese island just an hour from Rhodes, it has somehow remained almost entirely unspoiled — a working harbour town of neoclassical mansions painted in ochre, terracotta and gold, rising steeply from the water.
There are no large hotels. No beach clubs. No nightlife to speak of. What there is: exceptional tavernas, extraordinary swimming, a pace of life that feels genuinely Greek rather than performed for tourists, and a beauty that is almost architectural in its precision.
Symi rewards those who want to feel they have found somewhere real. And in 25 years, it has never disappointed a single client we have sent there.
If you love history...
Go to Athens — then Rhodes
Athens is not an island, but no Greek holiday is complete without it. The Acropolis at dawn, before the crowds arrive, is one of the most moving experiences available to any traveller. The National Archaeological Museum. The Plaka. The food scene, which has transformed beyond recognition in the last decade.
Pair Athens with Rhodes for a history-focused holiday and you have something extraordinary. Rhodes Old Town is a UNESCO World Heritage Site and the best-preserved medieval city in Europe. The Street of the Knights. The Palace of the Grand Masters. The ancient city of Lindos, perched above a perfect bay. Rhodes rewards the curious at every turn.
If you love beaches...
Go to Kefalonia
Myrtos Beach is the most photographed beach in Greece for a reason. The water is an almost unreal shade of turquoise-white, the cliffs are dramatic, and the setting is genuinely spectacular. But Kefalonia is far more than one beach.
The island has over 250 beaches, ranging from the famous to the completely deserted. Antisamos, where Captain Corelli's Mandolin was filmed. Xi Beach, with its distinctive red sand. The sea caves at Melissani. Kefalonia is large enough to feel like an adventure and beautiful enough to justify staying for two weeks.
It is also, in our experience, one of the most underrated islands in Greece. The food is excellent, the wine (Robola, grown in the island's mountain vineyards) is superb, and the people are among the warmest we have encountered anywhere.
If you love slow living...
Go to Halki
Halki is a tiny Dodecanese island — just 28 square kilometres — that has made a virtue of its smallness. There are no cars. No mopeds. No nightclubs. The island's single village, Emborio, is a cluster of neoclassical houses around a harbour so quiet you can hear the water.
Days on Halki follow a rhythm that feels almost forgotten: morning swim, long lunch, afternoon rest, evening ouzo. The island has a handful of excellent tavernas and a small but perfectly formed collection of accommodation options. It is the kind of place where you arrive stressed and leave transformed.
We recommend Halki to clients who have been to Greece before and want to go deeper. It is not for everyone — but for the right person, it is perfect.
If you love adventure...
Go to Crete (again)
Crete earns its second mention here because it is genuinely one of the most adventurous destinations in Greece. The Samaria Gorge — 16 kilometres through the White Mountains to the Libyan Sea — is one of Europe's great walks. The E4 long-distance trail crosses the island from east to west. The Imbros Gorge, less famous than Samaria but arguably more beautiful, can be walked in a morning.
Beyond hiking, Crete offers sea kayaking along the southern coast, mountain biking in the Lasithi Plateau, diving in the clear waters off Elounda, and jeep safaris into the island's wild interior. It is a large island with a huge range of landscapes, and it rewards those who want to earn their evenings.
If you love sailing...
Go to Paros
Paros sits at the heart of the Cyclades and is one of the world's great sailing destinations. The Meltemi wind — the strong, reliable northerly that blows through the Aegean each summer — makes the waters around Paros ideal for experienced sailors, while the sheltered bays and coves offer perfect anchorages for those who prefer to drift.
The island itself is beautiful: the marble-paved lanes of Parikia, the fishing village of Naoussa with its Venetian castle, the golden beaches of Santa Maria and Kolymbithres. Paros is also an excellent base for island-hopping — Naxos, Antiparos, Koufonisia and Ios are all within easy reach.
We often build sailing itineraries centred on Paros, using it as both a starting point and a place to return to.
If you love seclusion...
Go to Leipsoi
Leipsoi is one of Greece's best-kept secrets, and we intend to keep it that way — at least for our clients. A tiny Dodecanese island between Patmos and Leros, it has a permanent population of around 700 people and receives a fraction of the visitors that its more famous neighbours attract.
The island has one village, a handful of beaches, and a pace of life that borders on the meditative. The swimming is exceptional — the water around Leipsoi is some of the clearest in the Aegean. The tavernas are simple and honest. The nights are genuinely dark and genuinely quiet.
Leipsoi is for those who want Greece as it was. We love it unreservedly.
Not sure yet?
This is exactly the kind of conversation we love having. Tell us what you love, how you like to travel, and what you want to feel — and we will find your island. That is what we do.
Start planning your Greek holiday with Greeko, and let us match you to the place that is waiting for you.
Written by
The Greeko Team
Greeko has been crafting bespoke Greek holidays for over 25 years. Every article is written from genuine first-hand knowledge of the islands, the culture, and the experiences that make Greece extraordinary.
