Greek Islands: Which One and Why

Greece has 227 inhabited islands and several thousand more rocks with grass on them. The practical question isn’t “should I go to the Greek Islands” — it’s which one, when, and for how long. These are genuinely different destinations with different characters, different price points, and different types of visitors.

Santorini

The caldera views from Oia and Fira are extraordinary — a semicircle of white buildings on a cliff edge above a drowned volcanic crater. The sunset from Oia draws crowds that make it almost impossible to experience calmly; go to the castle ruins rather than the main terrace, arrive 45 minutes early, and accept that several hundred other people have the same plan. The beaches (Perissa, Kamari) are black sand and pleasant but not why people come. The wine is distinctive — the volcanic soil produces Assyrtiko with a minerality you won’t find elsewhere.

Santorini is expensive: €300-600+/night for cave hotels with caldera views in July-August, cheaper in shoulder season but still premium. The island gets 2 million visitors annually to a population of 15,000. Go in May or October if you have flexibility.

Crete

The largest island, with an airport at Heraklion and one at Chania, and enough variety to occupy two weeks without running out of things to do. The Minoan Palace of Knossos (15 minutes from Heraklion) is the most important Bronze Age site in the Aegean — 3,500 years old, partially reconstructed in controversial ways by Arthur Evans in the 1900s, but still overwhelming in scale. Entry €15.

The Samaria Gorge in the southwest (18km, 5-6 hours) is the most celebrated gorge walk in Europe. It descends 1,200 metres from the White Mountains to the Libyan Sea. The walk finishes at Agia Roumeli, a village accessible only by boat; ferries run to Chora Sfakion where buses return to Chania. Book the day before if weather is uncertain — the gorge closes when flood risk is high.

Chania Old Town (Venetian harbour, maze of lanes, Ottoman mosque converted to an exhibition space) is the most interesting urban area on the island. Stay within the walls if budget allows.

Rhodes

Medieval Rhodes Town is a UNESCO site — the best-preserved medieval city in the Mediterranean, with the Street of the Knights running from the harbour to the Knights’ Hospitallers Grand Master Palace. Genuinely good urban archaeology. Entry to the palace around €8.

Lindos (50km south) has a spectacular acropolis above a white village above two good beaches. The donkey ride up is for tourists; the walk takes 20 minutes on stone paths. Very crowded in summer; much better in May-June or September.

Lesser-Known and Worth It

Naxos is the largest of the Cyclades, has the best beaches (Agios Prokopios, Plaka), produces its own food (potatoes, cheese, citrus — things that make restaurants cheaper than on Mykonos), and has a medieval hilltop castle town above Naxos Town. Less Instagram-famous, substantially better value, a good balance of beaches and archaeology.

Ikaria in the eastern Aegean is one of the world’s documented “Blue Zones” — areas of unusual longevity. The islanders drink their own wine, walk between villages, eat together, and sleep irregular hours. The beaches are good (Messakti, Armenistis), the road signs are infrequent, and tourism infrastructure is minimal by Greek island standards. Not for people who need things organised.

Getting Around

Ferries connect the islands from Piraeus (Athens’ port). Blue Star Ferries and Hellenic Seaways operate most routes. High-speed catamarans are faster and more expensive; overnight conventional ferries for longer routes (Crete, Rhodes) allow you to sleep on the boat and save a night’s accommodation. Book ahead in summer — car spaces sell out first, then cabins, then deck tickets.