Kick off your trip with a couple of days in the capital, where
rooftop plunge pools and artisan boutiques pull in a creative and
buzzy crowd. A city best explored on foot, Athens has plenty of hip
hangouts and trendy tavernas to slip into, but first swing by the
Acropolis and the mythical Temple of Poseidon for an unmissable
slice of ancient Greek culture.

Come sunset, head to the breathtaking GB Roof Garden,
where spectacular views and a traditional Mediterranean menu await
– think grilled fish platters and tomato-packed pasta dishes. Once
you’ve finished taste-testing every dish, make a beeline for
The
Clumsies, which is acclaimed internationally for its
superlative cocktail list – a quirky selection split into three
emotions: tenderness, happiness and excitement. If you’re just as
indecisive as us when it comes to ordering, plump for the
award-winning Aegean negroni – a fresh blend laced with dittany
flower and bitter orange.

Look to rest your head at the 38-key boutique hotel, Ergon House. Upstairs, bedrooms are somewhat
reminiscent of upmarket spa treatment rooms: all exposed concrete
ceilings, terrazzo tiles and frosted glass. Downstairs, meanwhile,
guests can flit between an on-site deli, roastery and bakery, or go
all-in with a five-course meal in the state-of-the-art dining
area.

Take a direct flight from Athens to Milos. If you’d prefer to
soak up sweeping views of the sparkling Aegean, hop on a three-hour
catamaran ride from the port of Piraeus to savour the scenic route.
An island that’s well known for its 70-plus beaches, the locals are
justifiably proud of their ancient castles, catacombs and
amphitheatre ruins. Carve out a day to visit the no-frills capital
of Plaka, where you’ll brush shoulders with crowds of well-heeled
holidaying Athenians.

Craving a slower set-up? Make the northeastern town of Pollonia
your base. We’re checking into the sea-facing Milos Breeze Boutique Hotel. Perched on a
hillside overlooking the picture-perfect Pollonia Bay, 23 bright
and airy rooms enjoy a contemporary design, embellished with bamboo
headboards and sailor-blue linens. Start your day with a stroll
through the private, herb-scented gardens, before diving into the
enormous saltwater infinity pool.

Sundowners are best spent at the standout Akri,
followed by a home-style feast at O! Hamos!
taverna. We suggest bagging a table beneath the flower-clad pergola
and starting with a basket of warm bread – made even more delicious
with a side of freshly made tzatziki – before indulging in a
traditional Greek feast.

The dinky island of Folegandros is a two-hour ferry ride from
the bustling streets of Milos. What this place lacks in size, it
more than makes up for in community spirit. With family-run
eateries spilling onto a coastline fringed by emerald-green waters,
and 85 charming chapels tucked between cobblestone passageways,
we’re pegging it as the ultimate Grecian love letter to the world.
Become buddies with friendly fisherman returning with their daily
catch on the sultry sands of Agkali Beach, explore the
quintessential island town of Chora, or head out to sea on a
trivia-packed tour revealing the island’s hidden secrets. Whatever
you choose, the glitzy and glamorous Anemi Hotel should be your home-from-home,
while Papalagi restaurant delivers the goods when it
comes to all things seafood.

From the tranquil corners of Folegandros, make your way to the
culinary hub of the Cyclades – Sifnos. The island’s three main
villages – Apollonia, Artemonas and Kastro – are wrapped by rugged
valleys, terraced olive groves and knotted almond trees. We suggest
staying just outside of Apollonia at the Verina Astra hotel, whose 16 rooms sport brushed
concrete, rattan pendant lights and bamboo ceilings. Water babies
will delight in having their own terrace and private poolside
daybeds, while farm-to-fork lovers will relish tucking into dishes
crafted from freshly picked produce at the in-house Bostani
restaurant.