How to choose a Greek Island

Peering at a map of the Greek Islands, the mind boggles. It presents thousands of islands over roughly 1,300km². How the heck do you know where to start? Even worse: once you start looking, you’ll want to go everywhere, torn between seeing whether Santorini and Mykonos are really all that and retreating to an island where goliath cruise ships – and the thousands of people on them – can’t reach. Should you be island hopping in the Cyclades or staying put in rural Rhodes? Sailing, walking, cycling, or doing nada?
No one expects the Spanish Inquisition, but the only way to really know which Greek Island is best for you is to question exactly what you want out of this voyage.
What you want to do will inform which Greek Island to choose. We’d add to that some more food for thought. How about aiming for areas that aren’t sinking under the weight of tourists? The much-visited Cyclades will surprise you with their off-piste walking paths, for instance, while the people of Crete are keen to prod you out of Heraklion and into the White Mountains. Whichever Greek Island you choose, two things are guaranteed: boats and beaches.

Walking & cycling

Many walking holidays focus on the Cyclades – a circlet of islands strung between Crete in the south and Athens in the north. It’s a good balance of seeing the postcard Greek Islands in a way many don’t – via, say, the caldera footpaths of Santorini (Thira), gnarled olive groves of Naxos, and old Byzantine paths of Paros. You might want to get stuck into self guided hikes or leave the directions to a guide on a small group walking holiday.
Other walking holidays zoom in on the Ionian Islands. This cluster of isles in the northwest of Greece includes a few more famous faces – including Lefkada, Kefalonia and Ithaca – but offer ways to walk out of the crowded tourist traps. Fittingly, this is the land of Homer’s Ulysses. Your odyssey will tread in the Greek hero’s footsteps, along rich mountain valleys, river canyons, flowering forests and cave-chipped sandy coves.
Crete is great for cycling and driving. Tailor made self guided holidays give you full flexibility for shaping your trip to your needs in terms of kilometres, routes and rest days. Olive oil farms, pindrop-quiet beaches, impossibly picturesque mountain villages, and thousand year-old monasteries are all par for the course.

Sailing and small ship cruises

Sailing holidays usually stick to one dusting of islands. Surprise surprise, the Cyclades come out top again; they gather together a necklace of islands that is easily navigable in a week or two days. Yachting trips paint a bulls-eye on the deserted islands that hulking cruise ships can’t dock at. Iraklia is wild and remote hiking country; Kato Antikeri (population: two) serves up silent snorkelling and swimming holes; Ios is a little known bioluminescence glowspot.

Small ship cruises of up to sixty-ish passengers, meanwhile, aim for Santorini and Mykonos, while also paying attention to Poliegos (Polyaigos), where there are more goats than people, Amorgos and its cliff-face monastery, plus the birthplace of Apollo and Artemis at Delos.

Our top Greek islands Holiday

Luxury Greek Island holiday accommodation

Luxury Greek Island holiday accommodation

Organic country estate by the sea on Greek island of Ithaca

From €2495 to €4950 per week (sleeps 4-6)
Travel Team
If you'd like to chat about Greek islands or need help finding a holiday to suit you we're very happy to help.

Off the beaten track

You don’t have to commandeer a sailing boat and skipper to explore little visited islands – although a willingness to use the public ferries and catamarans is essential. You could stay in a plush Greek estate squeezed between perfumed pine forests and peaceful pebble beaches on Ithaca. Or join a walking tour to Tinos and Andros, or tiny Serifos. Where’s that, you say? Well, that’s the point. These islands are well off the tourist trail and offer hiking country that switches between gorges and waterfall-fed valleys, to pilgrimage paths that sew together churches, villages, windmills and farms.
Crete often rings alarm bells in terms of overtourism, but it’s a huge island, so you could take the long (and very scenic) route on a self guided cycling or driving holiday in the White Mountains. Elsewhere, conservation holidays go where the animals are – often far away from people. Give marine scientists a hand protecting dolphins in Alonnisos.

The classics

The windmills of Mykonos, sail-white villages of Santorini, beaches of Crete… There are reasons why these views are so sought after – they’re beautiful, but only if approached from the right angle. That is, an angle that 2,000 other tourists aren’t Instagramming. Classic island hopping cruises are best done in small ships that leave as little impact on the islands as possible. Or go on a holiday that uses public, Greek-run ferry transfers and stays overnight on each island you visit.

Or you could teach the kids to experience tourist-heavy Rhodes like a Greek – from the water. Some holidays offer sailing lessons with a local skipper and scuba diving sessions in little visited corners of the island. Meanwhile, many history tours take you to the most wanted archaeological digs, but thoughtfully, via hikes and museums like the oft-ignored Archaeological Museum and Bronze Age tombs in Lefkada.
Photo credits: [Page banner: lupu robert ciprian] [Top box: Chris Karidis] [Walking: iamadonut] [Off the beaten track: Luc.T]