Main Street, Oía, Santorini
The location in Oia is a big selling point for Hotel Kirini, which is more or less a living, breathing postcard-perfect village of typical Cycladic buildings carved into the sides of the cliffs. The hotel itself is dreamy, too. The minimalist, all-white guest rooms have super comfy beds, and there’s a spa on the property for facials and massages—a rarity for hotels in the Cyclades.
On the rim of Santorini's Caldera, each room at this small hotel is unique, decorated with original Greek art and a private balcony that looks over the surrounding villages and the Aegean. What makes Heliotopos so memorable, though, is the staff. Whatever you need—whether it’s booking a car, scheduling a boat tour, or even help tracking down lost luggage—they’ll make you feel like you’re the most important person in the world.
Kalo Livadi, Mykonos
Kalo Livadi Beach is one of the longest stretches of sand on Mykonos, and a good reason to book a room at Archipelagos (one of the nicer hotels on the island), which is only a few minutes’ walk away. Another bonus: a serene, ridiculously pretty swimming pool that’s an antidote to the thumping party-scene hangouts on other parts of the island. The rooms were recently renovated in crisp shades of white, grey, and blue, and each comes with its own ocean-view balcony.
Generally speaking, accommodations on Folegandros are mostly rustic and simple, but Anemomilos is an especially lovely option. It’s run by the Patelis family, who are always happy to give recommendations on what to do and see on their island. The rooms are a series of small, self-service villas with terraces right on the edge of a cliff, so the views are nothing short of incredible. The bar is a beautiful spot for a pre-dinner drink as the sun goes down.
Ahla Beach, Andros
One of the few Cycladic islands untouched by the masses of tourists, Andros is probably what you think of when you think of the perfect Greek escape. And there is no better way to take it in than at a hotel whose name means “dream” in ancient Greek. Guests lucky enough to occupy one of Onar's ten traditional cottages are treated to incomparable nature and wildlife as well as the utmost peace and relaxation. Situated in a protected wetland within a cove on the east coast of the island, the limited accommodations create an intimate, almost communal experience, all while maintaining a sense of privacy.
In the small, rustic village of Pollonia, Milos Breeze stands out for its sleek modernity (we could spend hours hanging out at the infinity pool). Every room has an ocean-facing balcony with a view you won’t ever tire of—and it’s the perfect spot to enjoy the hotel’s stellar breakfast of flaky spanakopitas (pastries filled with spinach and feta), freshly baked bread, and tart, homemade marmalade.
Naxian on the Beach
The best part about this hotel is the earthy, relaxed atmosphere.
The newish Mar Inn has something most other hotels on Folegandros don’t: air conditioning. For some people, that’s reason enough to book a room, but other bonuses include natural Korres beauty products in the bathrooms and super soft bathrobes. The hotel has two swimming pools, and the rooms are built to encircle them like a little Cycladic village that overlooks the sea below.
There are many things to love about Verina Astra. The location—hovering above Poulatis beach, with an ancient church next door and the gorgeous village of Artemonas just a short walk away—is hard to top. The accommodations are a series of small cottages, beautifully outfitted with smooth, brushed-concrete walls and floors and furniture in woven fabrics, like rattan and straw. The palette is all soft greys, white, and taupe with striped Turkish towels in the bathrooms, and each cottage has its own terrace. Those on the upper level offer the best views, as you feel like you’re somehow floating on top of the Aegean. For some—okay, maybe all of us—the infinity pool is the real draw, sheltered by stone walls on three sides: All you see is blue, blue, and even more blue.
Ktima Lemonies is the bed and breakfast of our imagination. Hidden on a three-acre private estate away from the center of town, the hotel includes an old farmhouse, stables, and stone cottages, all thoughtfully restored by the Greek couple that now owns and operates it. Complete with a quiet swimming pool, antique furniture, and country-style décor, this place is downright charming. Be sure to take a stroll through the heavenly gardens that wind through the property—you can even pick and eat fruit straight from the trees. Then sit back, relax, and...nothing.