We all fantasise about the idyllic Greek island getaway, dreaming of azure waters, luminous sunshine and white-washed hideaways that channel a serene Mediterranean vibe. With Greece boasting more than 6,000 islands, choosing between the postcard-perfect islands can be hard. Each differs significantly from one another in terms of architecture, scenery and nature. These are the best Greek Islands for affluent travellers and the best luxury Greek Island hotels, resorts and villas to stay in.
Milos
The volcanic island of Milos is renowned for its lunar-like landscape of hard black lava rock and soft white tufa stone, which form a spectacular coastline of cliffs lapped by turquoise waters that supply superb seafood. The Louvre’s marble Venus de Milos statue came from here. Experts say she’s not Venus, but the goddess Aphrodite moulded as the ideal embodiment of the female form. Milos is quite accessible with an airport and port serving ferries to and from Piraeus, Santorini, Ios, Sifnos, Folegandros and more. The ferry ride to Santorini takes two hours.
A must-do in Milos is to spend a day on a boat. A handful of yachts circumnavigate the island, taking in tiny fishing villages painted in candy colours as well as spectacular geological rock formations, sandy beaches and coastal caves, some of which you can swim through. Afterwards sate your hunger at family-run taverna O! Hamosn, near the port town of Adamas.
The taverna grows and produces almost everything on the menu: the owners’ farm supplies meat and vegetables, and the delicious cheeses are all house-made.
You can also take a 30-minute ferry to Kimolos, where you can hire scooters to explore pretty coves or simply stroll to the hilltop town with its beautiful citadel ruins.
Milos accommodation
White Pebble Suites
It feels apt that one of the three Greek Australian women who created the White Pebble Suites in the seaside village of Pollonia is named Aphrodite. The other two are Helen and Lefkothea. They fell in love with Milos while sailing the Aegean and hired a duo of female architects from Athens to replicate the creamy curvilinear shapes of the Milos coastline for their 12-suite luxury boutique hotel that sits at the water’s edge. Several suites boast infinity pools while all wrap around a lovely hotel pool that opens out to the sea. Guests enjoy an all-day menu of the freshest modern Greek specialties crafted by chef Konstantinos Slabakis, who was recently voted one of the top 100 chefs in Greece.
Folegandros
Around 50 kilometres northwest of Santorini, Folegandros has many of its bigger sister’s attractions – dramatic clifftop villages laced with bougainvillea and charming churches – but this Greek Island comes minus the crowds. The sparse and sparsely populated Folegandros is one of the smallest Cycladic islands and it still moves to an old-world beat. The main town Chora, with its ancient citadel, is among the prettiest in the Cyclades. Here, restaurants spill into gardens and squares, making the most of the island’s balmy summer weather. Blue Cuisine is highly rated for its focus on local produce. Sun-baked and treeless, Folegandros is a dramatic destination for hikes, with its extensive network of trails leading to scenic lookouts and hidden beaches like Hohlidia and Vardia. Climb the path to hilltop Panagia church for incredible views over the island. And nearby there are perfect spots to watch the sunset without the crowds. With no airport and only a tiny port, Folegandros is an under-the-radar Greek island.
Folegandros accommodation
Gundari Resort
The newest luxury resort to open in these parts, Gundari Resort, is the vision of Australian businessman Ricardo Larriera, who teamed up with acclaimed Athens-based design studio Block722 to craft 27 suites and villas above the island’s rugged cliffs. The resort’s ethos is all about wild understated luxury, which is perfectly expressed by the choice of stone, marble, timber and linen for the suites, each with private infinity pools, a flavour-rich modern Mediterranean cuisine crafted by Lefteris Lazarou (Greece’s first Michelin-starred chef), an expansive hotel infinity pool with sunken swim-up bar, and a spectacular clifftop spa, which embraces ancient Greek healing traditions that strengthen the connection between mind, body, and spirit.
Paros
Paros enjoys a pretty perfect Aegean perch, within easy reach of Mykonos, Santorini and Naxos. Plus, it comes with blissful beaches, trendy bars, restaurants, wineries and walking trails. Hopping between sandy coves like Kolymbithres and Santa Maria, then head to the town of Parikia, where you can explore atmospheric alleys and the historic church, Panagia Ekatontapiliani, also known as the ‘Church of 100 Doors’.
Paros Accommodation
The island of Paros is home to some of Europe’s most luxurious villas, and the travel experts at Five Star Greece can find you the perfect place to idle. Their portfolio covers Paros, with bespoke options provided upon consultation.
Antiparos
Antiparos is an island off an island, the island of Paros, to be exact. While Paros has become a popular Greek Island destination, Antiparos still moves to a slower rhythm yet the sinuous street that winds through its main village is filled with tasteful boutiques and bars that appeal to a well-heeled clientele. It’s just a short ferry ride to access the airport on Paros.
Antiparos accommodation
The Rooster
Spread across 12 wild hectares behind unspoiled Livadia beach, The Rooster’s 16 camouflaged private houses, forged from the very rocks of the landscape, are outfitted with carved four-poster beds, woven hangings, and other covetable organic touches. Each has a private pool or jacuzzi and outdoor rain shower. Here the focus is on slow living and a holistic approach to wellness with exquisite farm and fisher-to-table cuisine, as well as massages and facials that tap into a thoughtful range of authentic multicultural practices.
Sifnos
Not far from Milos, Sifnos has long appealed to sophisticated Europeans for its excellent cuisine, artisanal pottery, and network of ancient walking paths that crisscross the island. There are several pretty hilltop towns and low-key seaside villages, plus some of the finest blue-domed, white-washed churches in the Greek Islands. There’s no airport and the charming port of Kamares is not large enough to welcome cruise ships.
Sifnos accommodation
Verina Astra
Perched on a steep hillside on the eastern side of Sifnos, Verina Astra hotel sports 16 serene suites, crafted from the island’s red rocks and surrounded by wispy indigenous grasses, each with outdoor terraces that gaze out to sea. The blues of the infinity pool merge with the blues of the Aegean far below while the adjacent outdoor Bostani Bar and Restaurant, festooned with fairy lights strung between ancient olive trees, offers the same mesmerising vistas. Here, chef Nikos Thomas offers an inspired modern interpretation of Cycladic cuisine with ingredients sourced from nearby fishing villages and the restaurant’s expansive vegetable garden. Wedged into a corner of the hotel garden is Bostani Spa, also overlooking that dreamy sea.
Syros
With a medieval citadel, twisting lanes and little alleys, Syros is a picturesque island of Neoclassical buildings and terraces. Despite being the capital of the Cyclades with an airport of its own, it isn’t as busy as Mykonos or Santorini. Instead, the charming fishing villages and small harbours are frequented by the locals, who keep the island (and its excellent restaurants) open for business all year round, making Syros a fantastic off-season destination.
Fun fact: The name “Cyclades” means “encircling islands” because they form a rough circle around the sacred island of Delos, the legendary birthplace of the God Apollo and his Goddess twin sister Artemis.
Syros accommodation
Syros Villa
Designed by Athens-based architecture studio Block722, the Syros WG villa from Five Star Greece is an exceptional property perched on a hill overlooking the Aegean Sea. Spanning 500 square metres with terraces, a secret garden, pool, patios and rooftop hideaways, the five-bedroom private abode has panoramic 180-degree views from almost every bedroom and terrace. Stone, terrazzo, timber and natural materials appear throughout the elegantly furnished interiors. Equipped with all you need for a dreamy holiday, including a meet and greet on arrival, optional breakfast service, daily cleaning, a gym and a yoga terrace, the villa is an exclusive escape set upon 60,000 square metres of private land, just a five-minute walk from the beach.
Santorini
Most trips to Greece will include a visit to Santorini, where dreamy sunsets are glimpsed over whitewashed, cliff-hugging villages and bougainvillea drapes over blue-domed churches. Santorini is the island for lovers, as it exudes romance in its iconic architecture and awe-inspiring beauty. Aside from postcard-perfect towns, Santorini is known for its beaches, some of which have black and red sand. And then there are the wineries: grapes are grown in distinctive ‘baskets’ low to the ground, with the volcanic soil giving them a delicious, mineral-driven flavour.
Santorini accommodation
The stunning Katikies Hotel, a member of The Leading Hotels of the World, is situated in Oia and nestled on the caldera cliffs 90 metres above the azure waters of the Aegean. The hotel is an exemplar of contemporary design, with 27 lavishly designed rooms and 16 suites, perched in one of the world’s most incredible natural settings.
Santo Maris Oia Luxury Suites & Spa is an all-suite, all-villa retreat with an ocean-inspired spa and jaw-dropping Aegean views. The adults-only hideaway has five public pools that guarantee private sunset dips overlooking the Aegean.
