20 great islands of Greece

1 Agkistri
Little more than a hop, skip and jump from the Port of Piraeus (22 nautical miles, actually), rustic Agkistri is a popular escape for city-weary Athenians. There are no fancy hotels and not much to do other than bathe in its kaleidoscopic waters, eat fresh fish by the sea and chill out — but that’s the point. Grab a kayak and explore isolated shores and sea caves or hike your way between pearly white villages. 

2 Alonnisos
On this emerald green isle, just 12 miles long, you’ll find a paradisiacal riot of rare passion flowers, twisted olive trees and ripe apricots. The surrounding waters are a designated marine park that’s home to dolphins and endangered seals, while the island’s beaches, bays and rock pools provide a sublime summer playground. 

3 Astypalaia
Butterfly-shaped Astypalaia was almost an anonymous Greek island, but is now a favourite with the in-the-know crowd. This drop-dead gorgeous Dodecanese idyll combines sophistication with seclusion and is easy enough to reach, thanks to near-daily flights from Athens. Take a breather from the many beautiful beaches (the liveliest is Maltezana; the most escapist, Vatses, is reached only by boat) to potter around the dreamy hilltop town of Chora. The Baths of Talara, with their vivid Hellenic-period mosaics, are also well worth an Instagram salute or two.

4 Folegandros 
Greek islomaniacs rave about Folegandros’s simple unspoilt charms and wild mountainous bulks. On this calm and compact island of only 30 sq m, the capital, Chora, 200m above sea level, is among the most picturesque of the Cycladic settlements. There are sprawling pebbly beaches lined with tamarisk trees. Some of the best — Katergo, Agali and the clothing optional Agios Nikolaos — can be reached only by boat or hearty hike. Chrysopilia cave, at the foot of the Virgin Mary monastery, is home to remarkable stalactites and stalagmites. 

5 Monemvasia
The castle settlement of Monemvasia packs a wow factor to rattle even Santorini’s cage. Like Santorini, it owes its epic beauty to disaster — it was sheared from the mainland by a massive earthquake in about AD375. Perched 300m above the sea on a stark rock formation off the east coast of the Peloponnese, this sophisticated fortress town is linked to the mainland by a stone bridge and accessible only on foot through massive battle-scarred wooden gates. You can sleep inside the ancient castle walls in restored medieval monasteries and while the local wineries are among Greece’s best.

6 Halki
Very Greek, very sleepy Halki, with a population of only 400, is a charming hamlet of fishermen, small beaches and whitewashed chapels where Greeks go for much-prized tranquillity. A 75-minute boat ride from Rhodes, the Dodecanese island revolves around Emborio, a neo-classical jewel of a harbour. Away from the port, the loudest sounds you’ll probably hear are church bells or the occasional clang of a goat’s bell. Even the hands of the harbour clock were stopped years ago because its chiming was deemed too noisy. It’s that kind of place.

7 Skiathos
Pint-sized Skiathos, the smallest of the verdant Sporades group, is the perfect antidote for those who like their beach experiences Caribbean green, instead of the more austere Cycladic template. The Beatles so adored the island’s dramatic pine forests and sweeps of golden sand, they reportedly tried to buy one of its most idyllic islets (Tsourgria) for a recording studio. From the 60-odd beaches, the most famous — Koukounaries — has soft white sand set against a luscious green belt. 

8 Serifos
The chilled island of Serifos is a compact and unpretentious Cycladic treasure that’s become a haven for sophisticated Athenians and solitude-loving Europeans (without the eye-watering prices of Mykonos or Santorini). An easy two-hour ferry ride from Piraeus, the island has blissful beaches and Tahitian-coloured bays along its barren, cinematic coastline (if green is your scene, Serifos may not be for you). Swim at Psili Ammos, a fine sandy beach on the island’s eastern flanks.

9 Kea 
Join the stylish Athens set who love to dart over to this languid island, an easy one-hour ferry ride from Lavrio, in eastern Attica. Unusually green for a Cycladic island, Kea has an appealing independent spirit and has successfully dodged mass tourism. Eat the fresh fish at Voulkari Bay’s excellent waterfront tavernas (I Strofi tou Mimi is the most famous) and trek Kea’s ancient and well-organised panoramic trails. 

10 Kastellorizo
Tiny Kastellorizo is flung so far from the Greek mainland that it’s almost an afterthought on the map. But this arty island makes up for its geographical challenges by staging an entrance so pretty, it’s ridiculous. Chances are, by the time you’ve sailed past the ravaged castle and bright huddle of pastel neo-classical houses gracing the peacock blue bay, you’ll already be sold. Its steep and rocky contours don’t allow for much in the way of sandy beaches, but you’ll find many an idyllic swimming cove and sunbathing platform, as well as Parasta, possibly the Med’s most dramatic blue cave. 

11 Kythnos
Foreign tourists are few on this low-key Cycladic delight that’s a very Greek portal to simpler times. At the weekend the tavernas in Kythnos’s small traditional villages swell with Athenians who’ve made the easy crossing from Piraeus or Lavrio. There are more than 70 beaches on the island, but it’s exquisite Kolona, where a bright stripe of sand splits the sea in two, that they’ve all come to see. Follow the yachting crowd to the small port of Loutra to find hot healing springs and a lovely beach where you can eat grilled seafood on the sand. 

12 Sifnos
Tucked between Milos and Paros, Sifnos is a walker’s island that offers one of Greece’s richest terrains in terms of nature. It’s here in this lush interior of green hollows, beyond the unpromising Kamares port, that you see Sifnos’s true glories. Paths range from easy to moderate, including child-friendly trails, and take you past archaeological sites, functioning monasteries, hidden beaches and coves, traditional villages, terraced slopes covered in olive trees and juniper forests. Beach lovers will be thrilled by Sifnos’s lovely southern beaches, while foodies relish the island’s growing fame as a gastronomic stronghold. 

13 Lefka
Also known as Lefkada, Lefka possesses an easy charm, but is often passed over for the more publicised merits of nearby Corfu and Zakynthos. That means it’s been shielded from over-development, even though it is accessible by car via a short bridge, making it the perfect weekend getaway from Athens. Culture isn’t really part of the story here (especially in Nidri’s “golden mile” strip of sports bars). Instead, head to the hidden bays tucked between precipitous limestone cliffs, and to the enchanting small villages. Lefka’s most celebrated beach, Porto Katsiki, with surreal peacock-coloured waters, is frequently listed among the planet’s most stunning. 

14 Koufonisia
Koufonisia sits at that lovely pre-tipping point where word has got out about its ravishing charms, but for the moment at least this micro-island paradise near Mykonos still hangs on to its unhurried ways. It has lovely beaches and geological rock formations, along with a handful of chic restaurants and boutique hotels. But at heart this is a chilled, barefoot place where you can have dinner anywhere in your swimsuit and play boardgames with new friends made over driftless afternoons. Koufonisia’s headliner is magnificent Pori, an enormous white-sand horseshoe of a beach with iridescent blue waters in Ano Koufonisi. Avoid the island in August when the ferries overwhelm this bijou 25 sq km hideaway.

15 Symi
Small in size and rocky by nature, the Dodecanese island of Symi, just north of Rhodes, has a gorgeous neo-classical harbour with colourful mansions arranged artfully around a vivid blue bay. This island is the place to take water taxis to tranquil beaches, to eat great food in local tavernas (the Michelin-mentioned Muses, in the main square, is the most fêted) and go for long walks in the hills or amid the elegant lanes of the old town.

16 Paxos
This delightfully secluded Ionian enclave resembles a forest in the middle of the sea. It’s best explored by boat to see the most stunning sights: Galazio beach (the Blue Lagoon of the Med); the arresting rock formations of Kamara; and the nearby micro-satellite of Antipaxos, with its own lovely beaches, Voutoumi and Vrika. In the evening there’s waterfront dining on Paxos’s enchanted trio of neo-classical harbours, Gaios, Lakka and Loggos. Erimitis, an outrageously romantic restaurant, sits atop a 150m sheer drop of glowing limestone. 

17 Karpathos
One of Greece’s least-commercialised islands, this hefty Dodecanese paradise to the east of Crete has wildly beautiful blue coves. One side of the island is rocky, the other fertile and green. The gorgeous mountain village of Olympos spent centuries in isolation and residents still practise medieval crafts and rituals. You’ll find dreamy sweeps of beach, such as Lefkos and Apella, and, if you’re lucky, you may spot an endangered Mediterranean monk seal.

18 Samothraki
If you value the outdoors over fancy restaurants, Samothraki is the place for you. Off the northern coast of Greece, and reached only from the mainland port of Alexandroupoli, it has beautiful mountainous terrain with waterfalls at Vathres and reviving thermal springs at Loutra. In the south you will find prized beaches, such as Pachia Ammos, and one of Greece’s mightiest archaeological sites, the ancient Thracian Sanctuary of the Great Gods. Not bad going for a little fishing outpost that’s only 18km long and remains among the last truly untarnished islands of Greece. 

19 Amorgos
“Welcome to Amorgos. Nobody will find you here,” reads a sign on this fair Cycladic isle’s harbour. Amorgos’s fame flared brightly in 1988 when it was the backdrop for Luc Besson’s cult diving classic The Big Blue, but this most eastern of the Cycladics prefers the quiet life. Dramatic shipwrecks, sea caves and diving locales make it hard to beat. Be sure to visit the mind-blowing 11th-century Monastery of Hozoviotissa, carved into a vertiginous cliff. 

20 Syros
This Cycladic island’s heart is the grandiose capital of Ermoupoli (the city of Hermes), spread across two hills, one crowned with a Greek Orthodox church, the other a Roman Catholic cathedral. Beyond Ermoupoli’s spiderweb alleyways, Syros’s most enticing seaside resort is the tree-lined streets of Possidonia, where Onassis was a frequent guest at the popular casino. 

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