Greece has around 200 inhabited islands spread across six main groups, and they have almost nothing in common beyond the language and the sea. Treating them as one destination is the root of nearly every disappointed Greek island holiday — usually in the specific form of someone booking Santorini for a beach week and discovering it is a volcanic cliff with black gravel at the bottom.
Here is what each group is actually for.
The Cyclades — the postcard, and the crowds
Santorini, Mykonos, Naxos, Paros, Milos, Folegandros. White cubic villages, blue domes, bare rock, ferocious summer wind. This is the Greece of the photographs and the group most visitors book.
- Santorini is a drowned volcano and its appeal is the view down into the caldera. It is spectacular and it is not a swimming island. The beaches are black volcanic sand and gravel and are a bus ride from the villages where you will be staying.
- Mykonos is a genuinely good beach island with excellent food and Greece's most expensive nightlife economy. If the nightlife is not why you came, you are paying for it anyway.
- Naxos and Paros are what most people actually want when they say Santorini: proper sandy beaches, working towns, real agriculture, half the price, and a fraction of the cruise traffic.
- Milos has the most extraordinary coastline in the group and, so far, considerably fewer people.
- Folegandros or Sifnos if you want the Cyclades of thirty years ago and are willing to accept fewer ferries.
The wind is a real planning factor. The meltemi blows hard through the Cyclades in July and August — strong enough to cancel ferries for a day or two at a time. If your itinerary has a tight connection to a flight home, build a buffer day into the end of a Cyclades trip. This is the single most common way a Greek island holiday goes wrong.
The Ionian — green, gentle, and nothing like the postcards
Corfu, Kefalonia, Zakynthos, Lefkada, Paxos. On the west coast, catching Adriatic rain, so they are green rather than bare — cypress, olive, and a Venetian rather than Ottoman architectural inheritance.
The sea is calm, the beaches are sandy, and the whole group is dramatically easier to travel in than the Cyclades: shorter crossings, no meltemi, several islands reachable by road bridge or short ferry. This is the group for a first Greek island trip, for travelling with limited mobility, or for anyone who wants to swim every day without planning around wind.
The trade is that it feels less distinctly Greek and more generically Mediterranean, and Corfu and Zakynthos both carry large package-holiday resorts you will want to avoid by staying north or inland.
The Dodecanese — the history group
Rhodes, Kos, Symi, Patmos, Karpathos. Up against the Turkish coast, with the deepest layered history of any group: a medieval walled city on Rhodes that is still lived in, Crusader castles, Ottoman quarters, and on Patmos the monastery and cave associated with the Book of Revelation.
Come here if you want a holiday with something to read about. Rhodes Old Town is genuinely one of the great surviving medieval cities of Europe and is startlingly under-visited outside the cruise hours. Symi — neoclassical mansions stacked around a horseshoe harbour — is among the most beautiful arrivals in the Mediterranean.
Crete — not an island group, a small country
Crete is 260 km end to end with mountains above 2,400 m, its own dialect, its own cuisine and four distinct regions. You cannot see it in a week and you should not try.
It has the best food in Greece by a clear margin, gorges worth walking, Minoan archaeology, and enough infrastructure that you can travel it comfortably. Pick one end — Chania in the west for the Venetian harbour and the gorges, Heraklion in the centre for Knossos, the east for quiet — and stay there.
The Sporades and the North Aegean — for the second trip
Skiathos, Skopelos, Alonnisos; Lesbos, Chios, Samos, Ikaria. Pine forests running down to the water in the Sporades, which is a landscape you will not find elsewhere in Greece. The North Aegean islands are large, agricultural, barely touristed and closer to Turkey than to Athens in feel.
These reward a traveller who already knows Greece and wants somewhere without an English menu.
How to actually choose
| If you want… | Go to |
|---|---|
| The famous view, once, and you accept the crowds | Santorini — two nights, no more |
| To swim every day without thinking about wind | The Ionian |
| Beaches and real towns at a fair price | Naxos or Paros |
| History you can walk around in | The Dodecanese — Rhodes and Symi |
| Food, mountains, and a fortnight's worth of country | Crete, one end of it |
| Somewhere without an English menu | The North Aegean |
| The Cyclades before they were the Cyclades | Milos, Sifnos or Folegandros |
Two practical points that decide the trip
Ferries, not flights, set your itinerary. Islands in the same group are usually well connected; islands in different groups often are not, and the connection may run through Athens. Two islands in one week is comfortable, three is a travel week, four is a mistake. Check the actual timetable before committing — routes thin out sharply from late October.
Cruise calls now carry a levy. Santorini and Mykonos charge tiered cruise-passenger fees reaching €20 a head in peak season, falling away outside it. If you are arriving by ship, a May or October call costs a fraction of a July one at a port that is also far more pleasant to be in.
The short version
- Santorini is a view, not a beach island. Two nights, then move.
- Naxos and Paros are what most people mean when they say Santorini.
- The Ionian is the easiest group: calm sea, sandy beaches, no meltemi, short crossings.
- The Dodecanese is the history group. Rhodes Old Town is a genuine medieval city.
- Crete is a country. Pick one end.
- The meltemi cancels Cyclades ferries in July and August. Build a buffer day before your flight home.