The Greek Islands: Skip the Obvious, Find Something Better

Here is a fact that most Santorini brochures leave out: a pair of front-row sunbeds at a popular Mykonos beach now costs up to €200. That is before you have eaten anything. The Greek islands are genuinely, undeniably spectacular, but the two or three famous ones have priced themselves into a different market from the rest. The good news is that the Aegean has around 6,000 islands, and the second tier is full of places with the same white-cube architecture, turquoise water, and grilled octopus, at 40-60% of the cost.

That said, Santorini and Crete are on this list for reasons, and I will get to them. First, a word on how to think about the islands.

Which Islands Actually Work

Santorini earns its reputation. The caldera view from Oia at sunset is one of those experiences that lives up to the photograph, just barely, and only if you are there in late September rather than August. The crowds in high summer are genuinely oppressive: cruise ships dock daily and deposit thousands of people on streets designed for a few hundred. Visit in May, early June, or late September. The volcano geology (iron-rich red cliffs, black sand beaches at Perissa and Kamari) is unlike anywhere else in the Mediterranean, and the ancient Akrotiri site (a Bronze Age settlement preserved under volcanic ash, sometimes called the “Minoan Pompeii”) is worth a morning regardless of crowds.

Mykonos is for people who want a party. That is not a criticism; it just tells you whether it is for you. The windmills, the Little Venice waterfront, the labyrinthine Hora streets: all genuinely photogenic. If you are not there to dance until 4am on a beach, the island runs out of things to do fairly quickly.

Milos is the better call for anyone who likes dramatic geology without Santorini’s prices. Its 73 beaches include Sarakiniko, a stretch of white volcanic rock so lunar-looking that the photos reliably look like CGI. Sea caves accessible only by boat, colourful fishing village at Klima, and hotel prices roughly half of what Santorini charges. Milos has been growing fast (book accommodation well ahead in July and August), but it remains far less crowded than its volcanic neighbour.

Naxos is the island I keep recommending to families and to anyone who hates feeling rushed. It is the largest Cycladic island, with west-coast beaches that stay uncrowded even in peak season, mountain villages where you can eat roast lamb for €12, and an ancient marble doorway (the Portara, a giant unfinished temple gateway) standing alone at the harbour entrance that has been there since the 6th century BC. The island grows its own produce (Naxian potatoes and graviera cheese are nationally famous) and you can taste the difference.

Folegandros is small, dramatic, and genuinely quiet. Fewer than 800 permanent residents. The main village (Chora) sits on a cliff edge 200 metres above the sea, accessible from the port by a winding bus ride. No all-inclusive resorts, no mega-clubs. One reason to go: the Church of Panagia is carried by locals up a steep path from the cliff village to a higher peak for a festival in August that few tourists witness.

Hydra is the odd one out: a Saronic island close to Athens (two hours by hydrofoil from Piraeus), famously without cars or motorbikes. Donkeys carry luggage. The architecture is stately, 18th-century stone mansions rather than Cycladic white cubes. Leonard Cohen lived here for years. It is better as a 2-3 day visit from Athens than a week-long base, but those two days are excellent.

Crete deserves its own article. It is big enough to function as a country: different dialect, distinct cuisine, its own ancient civilisation (the Minoans), and enough coast to disappear for a fortnight without seeing the same beach twice. Heraklion’s Archaeological Museum is the best place in the world to understand Minoan culture. Chania’s Venetian harbour is one of the most photographed spots in Greece. The White Mountains (Lefka Ori) in the west allow serious hiking even in June. Avoid the north coast resort strip east of Heraklion in high summer; head instead to the south coast road between Loutro and Paleochora, accessible mostly by boat or on foot, where the crowds thin to almost nothing.

Getting Between Islands

Ferries are the default and are cheaper than they look once you accept the overnight option. Athens (Piraeus) to Heraklion takes 8-9 hours overnight; a cabin berth costs €25-40 and replaces a night’s accommodation. Inter-Cyclades ferries run frequently in summer. The Piraeus-Santorini conventional ferry costs €50-90 depending on the operator; the fast catamaran is 40% more but saves four hours if your time is short.

Book ferries 2-4 months ahead for peak summer, especially on popular routes and for cabin berths. Ferryhopper and the Greek ferry operator direct sites (SeaJets, Blue Star, Minoan) all work reliably for booking. Inter-island connections are good between major islands; getting to smaller ones (Folegandros, Anafi, Kastellorizo) requires patience and checking timetables carefully.

Flying between islands is possible but rarely worth the airport time and cost unless you are crossing from the Cyclades to Crete or to Rhodes. The ferry is almost always the better answer.

Where to Stay

The accommodation categories map to roughly three budgets.

For Santorini, Canaves Oia is the benchmark for caldera-view luxury. If you want the view without paying for a boutique hotel, some guesthouses in Fira (rather than Oia) offer caldera rooms at 30-40% lower rates. Budget travellers should consider a room in Karterados or Perissa and pay for one meal in Oia rather than staying there.

For Crete, the city of Chania has beautiful boutique hotels in the old Venetian quarter. Rimondi and Casa Delfino are consistently recommended; expect €120-200 per night in summer. East of Rethymno along the south coast, smaller family guesthouses often undercut Chania prices significantly.

For almost every other island, local family-run guesthouses and small apartments booked directly (not through the large platforms) tend to offer better rates and local knowledge. On Naxos and Milos, arriving in shoulder season (May or late September) and booking two weeks ahead is usually enough.

What to Eat and Drink

The honest summary: eat at tavernas away from the main tourist drag, order whatever they tell you came in fresh that day, and drink house wine by the carafe rather than bottles.

Grilled octopus hanging outside a harbourside kitchen is usually a good sign. On Crete, look for dakos (barley rusk topped with fresh tomatoes, mizithra cheese, and olive oil), stamnagathi (local wild greens, slightly bitter, dressed in lemon), and lamb slowcooked in a wood oven. On Naxos, order anything made with local graviera. On Mykonos, the kopanisti cheese (sharp and spreadable) is genuinely distinctive.

Lunch specials at Greek tavernas are worth knowing about: a full meal costs €10-15 at lunch versus €22-28 for the same dishes at dinner. The food is identical.

Raki (tsikoudia on Crete) is offered free at many tavernas at the end of a meal, alongside fruit. Accept it even if you do not drink much; declining is slightly odd.

Practical Notes

The best months are May, early June, and September. July and August bring reliable sun but also peak crowds and prices. September sea temperatures peak (the water has been heating all summer), the tourists thin noticeably after the 15th, and the light is extraordinary.

Greek ferry delays are real. Build buffer into connections, especially if catching a flight home. Do not book a flight home within four hours of a ferry arrival in Athens.

Tipping: round up at tavernas or add 10%; nobody expects more. Card payment is now widely accepted across the major islands.

A small overlooked fact: many island interiors are worth visiting. The mountain villages of Naxos, the inland citrus groves of Corfu, the Byzantine monastery at Toplou on Crete: all involve leaving the beach and a short drive, which is exactly why most visitors miss them entirely.