Anchored in the northeastern Aegean, rugged Samothraki is a
laid-back enclave of sleepy villages with panoramic views. Pack
hiking boots as well as a bikini: the island is crisscrossed with
numerous trails that wind along rocky gorges, passing waterfalls
and natural pools. Mount Fengari (meaning “moon”) is one of the
highest peaks in the Aegean and, according to mythology, the spot
from which Poseidon watched the Trojan War. Various routes of
different difficulties trace the peak’s foothills, many passing
vathres (lakes) that are perfect for mid-hike dips. Don’t miss the
natural hot springs at Therma, either.

Where to stay:
The Fig Tree House

Lying opposite the southeastern tip of the Peloponnese
peninsula, Kythira’s rocky canyons, sea-gazing cliffs and beautiful
beaches tell the island’s history (and mythology) in the historic
ruins that are scattered between its hidden coves and high, rugged
cliffs. Aphrodite is said to have been born on the island –
fitting, given its paradisiacal beauty. Once the crossroads for
Mediterranean trade, Kythira has an eclectic mix of Venetian and
Aegean architecture. Rent a car to explore, spying hilltop Venetian
castles and Byzantine monasteries from the road, before stopping at
a secluded pebbled beach for an afternoon laze. The idyllic capital
of Chora is packed with higgledy-piggledy artisan shops. Souvenir
shopping? Take home handwoven fabrics, locally gathered sea salt
and fatourada, the local liqueur.

Where to stay: Hidden
Retreats

Kythnos’ name comes from the Greek word meaning “to hide”, which
is fitting, given that it’s arguably Greece’s best-kept secret.
Athenians guard this Attica coast island closely – it’s a summer
retreat they’re reluctant to share with tourists. Small and
low-key, the islet wears all the typical colours of classic
Hellenic beauty: think sun-parched mountains ringed by green-blue
waters and plentiful shoreside tavernas studded with blue-shuttered
windows. For a culture hit, head to Panagia Kanala, one of the most
important pilgrimage sites in the Cyclades.

Where to stay: Cape Suites

Connected to the Greek mainland by a long causeway, the Greek
island of Lefkada has the unique claim of being the only Greek
island you can drive to – but we’d suggest taking the ferry from
Kefalonia for a more relaxed, two-and-a-half-hour journey. Visiting
the island is like going back in time: traditional village life
plays out on the streets, where inhabitants sit on doorsteps from
dawn to dusk, sipping strong coffee in the lazy morning light,
before switching to local wine in the cool evening breeze. It’s a
far cry from the summer humdrum of Mykonos or Corfu. Stumble across
forgotten villages and centuries-old wells dotted among ancient
olive groves, then hit the beach. The best coves are on the rugged
western coast.

Where to stay: Bohèmian Boutique Hotel Lefkada

Named after Icarus, the doomed youth who flew too close to the
sun, this wing-shaped Aegean island is known for its vivacious
silver-haired population – residents live longer than almost
anywhere else in the world. Rumours abound at what keeps Ikarians
so lithe, but general consensus is that a diet of primarily
vegetables, olive oil and herbal tea is responsible for their
glowing disposition and high birthday count. The late-night domino
games and blousy red wine might help, too. What’s certain is that
the mountain terrain – butter-yellow and rocky – has ensured most
islanders live an active lifestyle. Get involved by lacing up your
hiking boots and heading out on the paths that crisscross the
interior. Not unexpectedly for an island with an ageing population,
tradition is highly respected around here. Try to visit during a
panegyris (saint’s day festival), when there’s feasting and street
dancing until dawn across the island.

Where to stay: Anemoessa Luxury Villas

Greek, but with a distinctly Italian feel (it was ruled by the
country between the world wars), the Dodecanese island of Leros
doesn’t get the footfall of its glamorous neighbours, Kos, Rhodes
and Symi. For something a little different, though, we’d head to
the island’s southern town of Lakki, where eucalyptus-lined squares
are home to churches, clock towers, theatres and schools in a
strange mishmash of art deco, Bauhaus and Renaissance styles. This
strange infrastructure – labelled Italian rationalism – arrived on
Leros during the Italian occupation, when the Italian army
transformed the small town, then called Portolago, into a military
base. Today, a local movement to preserve the unique buildings is
underway.

Where to stay: Leros Windmills

Accessible from Athens’ main port by a (rather slow) ferry,
car-free Spetses is where Athenians head for summer. So, we’d
arrive in September to skip the urbanite crowds but still be in
time to make the most of the seasonal tavernas. This pine-scented
Attica island is incredibly proud of its history – it was the first
Hellenic outpost to raise a revolutionary flag in 1821, and a key
figure in the war of independence, Laskarina Bouboulina, hails from
here. You’ll spot remnants of this history across the island:
cannons ring the old harbour and a statue of the woman admiral sits
pride of place on the waterfront. Buff up on her story at the tiny
Bouboulina Museum, then hire an e-bike to explore the
island, stopping at pebbled beaches for secluded swims.

Where to stay: Poseidonion Grand Hotel

This tiny island (a mere 32sq km) is spectacular: picture
emerald-green water, deserted beaches and an undulating landscape,
all heady with the scent of wild thyme and oregano. The medieval
capital of Chora sits on a clifftop, making it one of the most
striking towns in all of the Greek islands. From there, walk up to
the white church dedicated to the Virgin Mary – the best place from
which to watch the sunset.

Where to stay: Anemi Hotel

Six hours by ferry from Athens, this rocky island is where to
head for some detoxing. Amorgos is known for its cliffside
monastery, Panagia Hozoviotissa, an ecclesiastical eyrie set some
300m above the Aegean that’s visible only from the sea. If a
monastic escape seems too drastic, we’d take to the trails: the
challenging 11.5km Palia Strata route starts from the main island
town and ends at the blue waters of Aegiali Bay, an area that’s
graced the silver screen in Jean Reno’s Le Grand Bleu. Stop by a
taverna for some typical Amorgos seafood: grilled red mullet and a
skorpina (scorpion fish) soup.

Where to stay: Villa Halkios Amorgos

With its rolling hills, clear waters and pretty churches,
Skopelos is so picturesque that Hollywood came calling: Mamma Mia!
was shot on the island. Fortunately, its time in the spotlight has
not resulted in hordes of tourists making their way to its shores,
and island life remains fairly unchanged. Sunburnt landscapes,
quiet tavernas and cobbled towns are yours for the taking – just
don’t start singing.

Where to stay: Evlalia Studios
& Villas

A visit to Alonissos should include plenty of time in the water:
the island’s National Marine Park is the largest marine-protected
area in Europe. Back on dry land, this is a lush, verdant
destination. Head to the old town of Chora to stroll streets
sprouting with flowers and fruit trees. In the evening, when
day-trippers have left, the distinctive scent of jasmine floats on
cool sea breezes. Before you go, grab a packet of sweets from the
Women’s Agrotourism Cooperative of Alonissos – actually,
considering the four-hour boat-ride back to Agios Constantinos;
grab two.

Where to stay: Villa Mirothea
Alonissos

Sound familiar? Pink Floyd fans might know this place as
“Castellorizon”, the title of the Grammy-nominated song inspired by
Dave Gilmour’s jaunts on the island. Of course, it comes with all
the secluded, pine-fringed shorelines you’d expect from a
Dodecanese idyll, but the main village, a dusty riot of pink,
yellows and green neoclassical buildings that hug the bay, is the
real draw. It might be the largest island in an archipelago of the
same name, but ferries to Kastellorizo only run a few times a week,
meaning it has remained a highly exclusive destination.

Where to stay: Villa Zoe