The 10 Dreamiest Hotels in the Greek Islands

  • 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?

    Courtesy of Iconic Santorini, a boutique cave hotel

  • 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.

    Courtesy of Kalesma Mykonos

  • 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.

    Courtesy of Iconic Santorini, a boutique cave hotel

  • 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.

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

  • 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.

    Yannis Rizomarkos

  • 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.

    Courtesy of Anemi Hotels

  • 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.

    Courtesy of White Pebble Suites

  • 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.

    Courtesy of Coco-Mat Eco Residences Serifos

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