Spend your days wandering small, sherbet-coloured alleys,
investigating the cool interiors of myriad local churches and
sipping the excellent local wine on a trip to Symi. Once known for
its ship-building industry, the warm-hued harbour capital holds the
same moniker as the island, and tumbles down a natural amphitheatre
of hills towards a picturesque waterfront that’s perfect for dusk
dining. You’ll notice the muddle of pastel-hued homes are
distinctively un-Hellenic in looks; Symi’s golden era arrived in
the 19th century, when neoclassical, Venetian-inspired architecture
was all the range. Bring walking shoes – there are barely any cars,
but hiking routes aplenty.

Where to stay: The Old
Markets

With over 70 beaches, each enclosed by rugged cliffs and the
Aegean’s Gatorade-hued waves, Milos is a sun-seeker’s paradise –
but that’s not all the island has to offer. Just a short walk
beyond the beaches lie ancient catacombs, castles, amphitheatre
ruins and the iconic Papafragas’ aquamarine swimming hole (look it
up, you’ll want to go). Meander through the island’s labyrinthine
capital, Plaka, or head north-east to Pollonia, for harbour-side
restaurants and wineries.

Where to stay: Skinopi Lodge

While many have heard of Ithaca,
few have made the trip. Known as the homeland of Homer’s Odysseus,
this myth-swirled island does not disappoint. You’re unlikely to
find any cyclops, lotus eaters or witches turning men into swines,
but a trip around its coastal curves will lead to encounters with
seductive emerald coves, ancient castle ruins, and 16th-century
church frescoes. We know which we’d rather meet.

Where to stay: Levendís
Estate

Only a couple of hours flight from Athens (or an hour on the ferry from Piraeus,
the capital’s main port) Hydra has long been a haven for the art
crowd. Home to the School of Fine Arts, this car-free island offers
rugged cliffs, stone-grey mansions, wandering donkeys and steep
steps that lead up into isolated, quaint towns clinging to steep
hillsides. There are no large-scale hotels; only small, bohemian
stays and cute cafés inviting you in for a glass of perfectly
chilled rosé.

Where to stay: Cotommatae
Hotel

This pine-scented isle in the Attica region of Greece was the
first Hellenic outpost to raise a revolution flag in 1821,
declaring independence from the Ottoman Empire. Today, despite a
sleepy countenance, the tranquil isle retains a strong identity.
Residents are reluctant to be grouped with their neighbouring
Saronic islands, preferring to embrace a solitary life adrift in
the Aegean. They’re also proud of their fiery history: cannons ring
the Old Harbour of the largest town, Dapia, and the legacy of a
revolutionary widow, Laskarina Bouboulina, who left her whitewashed
mansion to lead a naval fleet to victory, is a source of immense
island pride. Catch up on the history at the Bouboulina Museum, then circumnavigate the island in
search of its myriad pebbled coves – visitors are banned from bring
cars, so you’ll need to hire a bike.

Where to stay: Poseidonion Grand
Hotel

This sleepy island has no flashy hotels, barely any shops and
minimal nightlife. Away from the hedonistic crowds of its
neighbour, Mykonos, Serifos’ dramatic landscapes and sweeping
solitude are an estoric sun-trap, providing escapism and seclusion
(no White Isle antics, please). The best beaches are accessible
only by dirt roads and boats, but their calibre is worth the added
effort. Hungry? Head to the quiet, taverna-lined harbour in Livadi
for piled-high platters of seafood and carafes of crisp local
wine.

Where to stay: Faros Guest House

Tiny Tinos boasts more than 50 villages dotted
between thyme-scented hillsides and sprawling vineyards. Most are a
model of Cycladic minimalism, complete with whitewashed cuboid
homes, tavernas outfitted with blue-legged tables and the island’s
much-loved windmills. You’ll notice lots of white marble around;
famed Greek sculptures including Gyzis, Lytras, Chalepas and Sochos
have all called Tinos home. Take up a chisel yourself at the
Dellatolas
Marble Sculpture School.

Where to stay: Villa Ghita

Andros’ ancient name, Hydroussa, is a perfect encapsulation of
its geography. The word means ‘watery’, a nod to the four rivers
that burble up between the island’s lush hills as springs, streams
and waterfalls. Differing from the rocky crags and dry winds of its
Cycladic neighbours, Andros is a verdant isle. The best way to
explore? On foot. Cross ancient stone bridges, and meandering along
old goat-trod paths, passing the cool cloisters of the island’s
many monasteries, as you find your way to the low-key villages
fridging the island shores.

Where to stay: Onar