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The 10 Dreamiest Hotels in the Greek Islands

No need to pinch yourself!

There exist few more breathtaking natural landscapes than those found in the Greek Islands. From remote sandy beaches inviting you into tepid turquoise waters to white-washed hilltop villages revealing centuries-old traditions. The feeling of Greece is unique.

Having visited over 15 islands, many belonging to the Cyclades in the southern part of the Aegean Sea, allow me to introduce you to the stays that top my list. Is there a better way to island-hop in Greece than through dreamy properties that provide the ideal setting for your adventure?

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PHOTO: Courtesy of Kalesma Mykonos
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Kalesma Mykonos

WHERE: Mykonos

For choice beaches and unrivaled nightlife, dock at scenic Mykonos with its iconic 16th-century windmills. Translated to “inviting” in Greek, luxury boutique hotel Kalesma Mykonos does exactly that. Set on a hilltop above Ornos Bay, two miles from bustling Mykonos town, each of Kalesma’s 25 accommodations offer patios with unobstructed sea views overlooking private heated pools. Every detail throughout the five-acre property is a work of art including Cycladic minimalistic ceramics by Serbian artist Aleksandar Vac and effortlessly cool furniture by designer Rick Owens. Wake up to the soundtrack of the sea followed by a serene spa treatment or energizing yoga class while a DJ sets the mood at the Mediterranean-inspired restaurant Pere Ubu.

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PHOTO: Courtesy of Iconic Santorini, a boutique cave hotel
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Iconic Santorini

WHERE: Santorini

A visit to Santorini, with its dramatic caldera and volcanic beaches, feels much like entering a dream. The experience becomes even more surreal when staying at Iconic Santorini set within the cliffs of the caldera in the picturesque village of Imerovigli. Each of the 20 cave-carved rooms and suites within this luxurious boutique hotel known for its Hellenic hospitality includes a personal terrace with breathtaking views of the volcano. Revitalize your body and mind with a signature holistic massage at the Wellness & Fitness Center before taking a dip in the jetted grotto pool. Inhale the views of Oia in the distance from within your private jacuzzi in between traditional Greek feasts at Pergola Restaurant. The only danger at Iconic Santorini is that you won’t want to check out.

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PHOTO: John Kilpasis (@johnkilpasis), Giagkos Papadopoulos (@giagkos_p) & Iosif Chatzimichail (@iosifchatzimichail) / Courtesy of Pylaia Boutique Hotel & Spa
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Pylaia Boutique Hotel & Spa

WHERE: Astypalaia

The perfect perch from which to discover this butterfly-shaped island of wild beaches and hilly terrain where the Dodecanese meets the Cyclades is Pylaia Boutique Hotel & Spa. Named after an old alias of Astypalaia, Pylaia is just 300 meters from the Chora, one of the most charming capitals in all of Greece boasting eight traditional windmills and a Venetian castle. Blending in with the landscape, each of the 26 modern rooms and suites plus the Pylaia House with private pool, are outfitted in natural elements, with sustainability at the core. Dine on Italian cuisine with a view at Cucina Restaurant & Bar, whose well-curated wine cellar merits a visit, and sink into Petra Wellness & Spa for a detoxifying body treatment using algae or a facial treatment with honey and royal jelly.

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Aegialis Hotel & Spa

WHERE: Amorgos

Step into the soul of the Cyclades when you arrive in Amorgos, known for its remarkable monastery of Hozoviotissa, wedged into the side of a cliff 300 meters above the sea. It’s also the enchantingly rustic Chora that leaves an impression. Discover this island, dotted with secluded beaches where the film The Big Blue was set, from the most luxurious address on the island, the Aegialis Hotel & Spa. This 55-room family-run oasis overlooking the Bay of Aegiali includes a Junior Family Suite with a shaded veranda and a two-bedroom Spa Suite. Find your zen at the Lalon Idor Spa’s thalassotherapy center, or take a yoga class at this popular address for yoga retreats. Amenities also include the organizing of activities, from scooter rentals to cooking classes, via Aegialis Tours.

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Parīlio

WHERE: Paros

The mountainous island of Paros sets an unforgettable Cycladic scene with its vast stretches of sandy beaches, white-washed fishing villages, and ancient architecture. In the northwestern corner, discover the timeless beauty of Parīlio, led by Kalia & Antonis Eliopoulos. Its name combines Paros and ilios, the Greek word for sun, and this luxuriously understated 33-suite haven is crafted in a soothing color palette using all-natural materials, accented by artwork. Head to restaurant Mr. E for a taste of the local Parian cuisine prepared by celebrated Chef Alexandros Tsiotinis. Select plants and herbs growing in the verdant landscape surrounding Parīlio are used in the holistic treatments at Elios Spa, further contributing to the organic ethos.

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PHOTO: Yannis Rizomarkos
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The Rooster

WHERE: Antiparos

The sister island to Paros, Antiparos presents a laid-back vibe that can easily be called hippie-chic. When not wandering along the bougainvillea-lined streets, visit the 15th-century Venetian castle, the oldest stalagmite in Europe at the Antiparos Cave, or the Historical and Folklore Museum of Antiparos. The top unpretentious option with aesthetic luxury and mindful living at the core is The Rooster. This wellness and lifestyle resort nestled between the beach and the dramatic Cycladian landscape is comprised of 17 independent houses with private gardens, outdoor showers, and inspiring views. Dine on farm-to-table cooking, grown on the resort’s own farm, before heading to the holistic spa to balance mind and body.

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PHOTO: Courtesy of Anemi Hotels
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Anemi

WHERE: Folegandros

When it comes to unspoiled Greek islands, Folegandros tops the list. Composed of three main villages–Karavostasi, Chora, and Ano Meria–there’s plenty to see and do, including walking the zigzag path up to the famous Panagia church. Not far from the port, hotel Anemi welcomes guests with an infinity pool set against 44 villa-style rooms and suites illustrating simple and harmonious luxury. The Grand Sea View Suites set on two floors offer unrivaled views of the Aegean along with their own pool. From the SEA SENSE restaurant, whose culinary options include traditional dishes from all over Greece, to a hatha yoga class in the vineyards or an energy healing massage, Anemi caters to all the senses.

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PHOTO: Courtesy of White Pebble Suites
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White Pebble Suites

WHERE: Milos

Lauded for its remarkable beaches and volcanic landscape, Sarakiniko Beach being the best example of both, the island of Milos is a paradise found. It’s the birthplace of the Venus de Milo statue, discovered in 1820. After exploring the beaches of Milos by catamaran, head to the pretty port of Pollonia and settle into White Pebble Suites. This couples-friendly hotel is a contemporary composition of 12 suites marrying cool marble with warm wood–an architectural exercise in Cycladic minimalism. The spa at White Pebble Suites takes its cues from the island’s healing energy. Much the way each hot spring contains different medicinal qualities, so too does each body therapy and beauty treatment.

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Verina Astra, Verina Terra, Verina Villa

WHERE: Sifnos

Known for its beaches and hiking paths, the increasingly fashionable island of Sifnos, with its traditional Sifniot pottery, is also an island for gourmands. One dining option set on the side of a hill overlooking endless views of the Aegean and blending into the landscape is a boutique hotel, Verina Astra. Each spacious suite where stargazing is a nightly ritual is named after a constellation. Their second property, Verina Terra, whose accommodations include apartments, is set amidst olive trees near Platys Gialos beach. Step even further into exclusivity with your own swimming pool, tennis court, and hammam at Verina Villa on Vathi beach. All of the gastronomic restaurants at Verina Hotels grow their own produce.

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PHOTO: Courtesy of Coco-Mat Eco Residences Serifos
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COCO-MAT Eco Residences Serifos

WHERE: Serifos

The laidback island of Serifos seduces subtly with its charm-ridden white-washed villages and off-the-beaten-path beaches. Slow down when you settle into COCO-MAT Eco Residences Serifos on Vagia beach, once a complex of miners’ houses. These elegantly eco-friendly residences outfitted with COCO-MAT sleep systems are split between two levels and look out onto the sea. The décor combining all-natural materials including coconut fibers, eucalyptus, and lavender, guests can choose what their mattresses and pillows can be made with. Following a sound sleep and invigorating swim, indulge in traditional fare and sunset cocktails beneath a kaleidoscopic sky at the beachside lounge bar.

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