Greek Islands: Which One and Why

Greece has 227 inhabited islands and several thousand more rocks with enough grass to argue the point. 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 expectations about what a holiday should involve.

Santorini

The caldera views from Oia and Fira are extraordinary: a semicircle of white buildings on a cliff edge above a drowned volcanic crater formed by one of the most violent eruptions in human history, around 1600 BC. The sunset from Oia draws crowds that make it nearly impossible to experience calmly. Go to the kastro 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 unlike anything from mainland Greece.

Santorini receives around 2 million visitors per year to a population of 15,000. Hotel prices run €300-600 per night for caldera cave hotels in July and August, dropping significantly in shoulder season. Go in May or October if you have any flexibility; the landscape is identical and the experience is substantially different.

Crete

The largest island, with airports at both Heraklion and Chania and enough variety to occupy two weeks without repetition. The Minoan Palace of Knossos (15 minutes from Heraklion) is the most important Bronze Age site in the Aegean, 3,500 years old, partially and controversially reconstructed by Sir Arthur Evans in the early 1900s, and still overwhelming in scale. Adult admission is €20; combined with the Heraklion Archaeological Museum (which holds the original frescoes and the undeciphered Phaistos Disc) for the same price.

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, finishing at Agia Roumeli, a village accessible only by boat. Ferries run to Chora Sfakion where buses return to Chania. Book the day before; the gorge closes when flood risk is high.

Chania Old Town with its Venetian harbour, labyrinthine lanes, and Ottoman mosque-turned-exhibition-space is the most interesting urban area on the island. Stay inside the walls if budget allows; the restaurants within walking distance are the best on Crete.

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. Entry to the palace around €8. The town is worth a full day of walking.

Lindos, 50km south, has a spectacular acropolis above a white village above two good beaches. Very crowded in summer; considerably better in May, June, or September when the temperature is manageable and the tourists are fewer.

The Case for Naxos and Ikaria

Naxos is the largest of the Cyclades, has the best beaches in the island group (Agios Prokopios, Plaka), and produces its own food: potatoes, cheese, and citrus that make restaurants noticeably cheaper than on Mykonos or Santorini. The medieval hilltop castle town above Naxos Town has a Venetian character most visitors miss by staying on the beach. Naxos is less Instagram-famous and substantially better value; it is the Greek island the author would actually return to.

Ikaria in the eastern Aegean is one of the world’s documented Blue Zones, areas with unusually high concentrations of people living past 90. The locals drink their own wine, walk between villages, eat communally, and sleep irregular hours. The beaches are excellent (Messakti, Armenistis), road signs are sparse, and tourist infrastructure is genuinely minimal. Not for people who need things organised. Exactly right for people who don’t.

Getting Around

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