After a trip to Antiparos left Athenian Athanasia Comninos
smitten by the under-the-radar island’s rugged, unspoilt beauty,
she decided to commit herself to the holiday romance and build a
hotel there. Settling on the tranquil beach of Livadia, Comninos’
slow-living-inspired The Rooster is an ode to the wild Antiparian
hills: 16 private villas blend softly into the natural landscape,
each with an accompanying pool. A short walk from the properties
sits a traditional “bostani” – a bountiful garden whose produce is
used in the resort’s farm-to-table restaurant. The real draw,
though, is the spa: picture a first-class wellness destination
replete with Ayurveda-led treatments, talented practitioners,
natural products and a heaven-sent relaxation area.

Tucked into the pastel-hued harbour of Syros’ main town,
Hermoupolis, Hotel Aristide showcases the creativity and
craftsmanship of this lesser-known Greek island. Nine individually
designed suites offer a harmonious blend of modern amenities and
restored furniture, while natural stone and wood flooring, rich
colours and nine different types of marble are used throughout the
property. Housed in a neoclassical mansion that was once the
island’s tax office, Aristide’s combination of old-world elegance
and well-considered design makes for a contemporary, yet opulent,
feel. Its eco-credentials are top notch, too – leftovers are
churned into compost, trees are planted to help guests offset their
carbon emissions and single-use plastics have been swapped for
refillable containers.

Read Oana Aristide’s insider guide to Syros,
Greece

The winds of change are sweeping through Mykonos and the
island’s dawn-till-dusk reputation is making way for a post-party
future. Located far from the crowds of the island’s south-west
coast, Kalesma’s 25 sugar-cube suites and two villas offer a new
breed of Mykonos stay. Scattered across the rugged slopes of the
bay of Ornos, these pared-back pads are equipped with picture
windows that guarantee both sunrise and sunset views throughout the
spaces – a rarity usually reserved for the superyachts found
bobbing in the Aegean. Every room has its own private pool, an al
fresco shower, a terrace for entertaining and Sonos surround sound
system to keep the island’s hedonistic vibes flowing. The
restaurant serves grilled seafood, and rejuvenating,
spirulina-spiked cocktails.

Calling all barefoot bohemians: at the 10-suite Naxian on the
Beach, days are spent sea-gazing, and little else. Screened from
the golden caster sugar sands by breeze-tousled grasses, this
adults-only boutique hotel feels like a natural continuation of the
bay it sits on, and ample use of wicker, basket, bamboo and natural
wood in its architecture and interiors amplifies the feeling. All
suites have balconies overlooking the waves, and some are equipped
with hammocks and outdoor spa bathtubs, too. The restaurant –
Tortuga – serves up modern Greek fare in an open-air dining space.
There’s no pool, but you’re encouraged to dip your toes into the
sea and all guests are allocated a sun lounger for all-day
R&R.

Perched above a rocky, rugged shoreline, Soho House’s first
iteration in Greece inhabits a prime spot on Mykonos, offering epic
views of the Aegean. Sure, it’s not technically boutique – but this
building’s history and importance on the Mykonos scene make it
worth an entry. Once San Giorgio, a pop-up hotel by Claus
Sendlinger, CEO of Design Hotels, the cluster of Cycladic buildings
was taken over in 2019 by the mighty members’ club, alongside the island’s
much-loved Scorpios bar, and reopened in 2020 following a
light-touch makeover. The property’s 45 rooms are made up in
typically snappable Soho style, though there are distinctive nods
to the hotel’s former boho-luxe interiors: spot the rattan chairs,
jute rugs, kilim cushions, weathered wooden furnishings and
hammocks dotted around. Elsewhere, there’s a gym, treatment rooms,
pool bar, open-plan restaurant serving fresh, colourful Greek
favourites and – a stone’s throw away – the hedonistic
Scorpios.

Barbican lovers, step this way. Tucked into lush verdure, with
views of the Ionian Sea, Olea is modern and minimalist – a
dove-grey, stripped-back, concrete beauty whose strong lines are
offset by extravagant water features and the soft, silvered
greenery of ancient olives trees. With 93 terraced suites, four
restaurants, three stylish bars and a spa, you’d be forgiven for
being overwhelmed by the choice on offer. One of the easier
decisions to make is where to sunbathe and swim – the best beaches
in Zakynthos are just minutes away.

In the 60s, socialites would flock to this hotel, with past
guests including Jackie Onassis and Brigitte Bardot. Now, Mykonos
Theoxenia has been renovated from Mick Jagger’s old party pad into
a peaceful hideaway, swapping its former summer-of-love colours for
stripped-back neutrals – think bouclé chairs in warm seashell hues
– and an aura of calm. The hotel’s history isn’t completely
forgotten, though. Vintage details such as a typewriter and rotary
phone are hidden like Easter eggs throughout the property,
connecting the minimalist interior with its eccentric past, and the
hedonistic nightlife of Mykonos Town is still just a cab ride
away.

Coco-Mat Eco Residences was doing sustainability before it was
cool, and its Serifos stay – a bioclimatic complex of 13 renovated
19th-century miners’ houses – was a game-changing Greek stay when
it opened in 2019. Eco-friendly apartments equipped with
kitchenettes, ranging in size from one bedroom to family
residences, have been transformed using natural materials:
everything from the sofas and chairs to the kitchens are made with
cotton, natural rubber, wood, silk and coconut fibres. Come for the
Cycladic design and sophisticated eco-friendly construction; stay
for the soothing sound of the waves.

Drawing on Paros’ cultural heritage, this recently opened hotel
has been designed to feel like the local villages that surround it.
Meander through the indigenous Parian architecture of its rooms and
suites and you’ll feel like you’re wandering the labyrinthine
streets of a particularly perfect Greek hamlet. Cosme’s 40 guest
rooms, each with a celestial-inspired name, have calming
caramel-coloured walls hung with a distinctive collection of
multimedia art, sourced from local artists. Open terraces with
sunbeds allow the sounds of the hotel’s “streets” – and those from
Naoussa, a little further away – to float through. Spend afternoons
racing the waves on the property’s privately owned catamaran or
take a few hours on Agioi Anargyroi beach, then enjoy a lavish
seafood banquet at Parostià Restaurant, named in tribute to Parian
stone ovens.

Famed for its infinity pool spilling over a volcanic caldera,
this five-bedroom retreat quite literally hides away in the rocky
cliffs that surround it. Doing away with the whitewashed,
blue-shuttered template of a Greek island retreat, Perivolas is a
former pumice mine that was built from the local reddish rock, so
it’s barely distinguishable against the scree-cloaked landscape.
Inside, interiors are more typical, with minimalist design making
the views outside the window the focus, and there’s a seawater
pool, a wellness suite and a private beach. Reachable by boat or
helicopter (if that’s your vibe), it’s a splash-out option. In the
unlikely event that you want a change of scenery, Santorini is only
a short boat ride away – but we’re pretty you won’t want to leave
the idyllic Cycladic islet.

Forget what you thought you knew about cave stays in Santorini –
the softly lit, cocoon-like suites at Divine Cave Experience are a
cut above the rest. A luxury hotel sculpted from the volcanic rock
of the island’s caldera, its 10 unique rooms feature low-curving
ceilings and arching walls that wouldn’t look out of place in Kim
K’s LA home. Serenely concealed from the village behind it, each
room has a secluded terrace, with Jacuzzi, that offers private
views of the Aegean’s azure waves. Rooms are minimalist (and not
huge), but if you’re looking for an all-natural, earthly retreat,
this is it.