Postcard from the Cyclades
The world is wide and there's always more to see, and we know that keeping track of the wheres, whens, whats, and hows of travel is quite a task. But that's what we're here for! The Postcard is Local Foreigner's guide to the quick hits of a trip - the highlights we want to send back to travelers when we're on the ground in a place.
There are more than 6,000 islands in Greece, and six major chains that curve around the mainland like a wreath of laurel. But the best known are the Cyclades, which legend holds started as hundreds of nymphs that Poseidon turned into islands in a fit of rage. Appropriately, every island has its own distinct personality - see-and-be-seen Mykonos boasts vibrant nightlife, Santorini attracts honeymooners from across the globe, and Apollo himself was born on Delos; you can choose one or two and settle in, or go where the wind (and its corresponding Greek God, Aeolus) takes you.
With whitewashed villages spilling down hillsides, their blue shutters thrown open to the sea, the Cyclades are the sort of place that look exactly how you pictured. Bop around the different islands by charter, letting the itinerary unfold bay by bay: long swims off the stern, lazy lunches in a hidden taverna, golden-hour arrivals into a harbor that’s all clinking glasses and bobbing boats. Or, if you're the sort of traveler who likes to park yourself somewhere, there are excellent villas dotted across the islands, where the kids can spend all day in the pool while your local chef whips up the day's catch in the kitchen. Traveling lighter? There are also plenty of breezy hotels bathed in that Aegean light that will have you considering pulling a Mamma Mia and relocating permanently.
May to early October is prime time in the islands.
Meltemi winds, which the area is famous for, show up in July and August, and can kick up waves (and mess up hair), but that's not going to stop the scene on islands like Mykonos, which are in full social swing during high summer.
One of our favorite times to visit is late August into September, when the winds have died down but water is still warm enough for swimming.
Most Cycladic hotels are small and start to book up over peak summer dates by early spring, so we’d recommend planning as late as February if you are looking to get that tan over the summer holidays.
The major Cycladic islands each have big personalities and the sweeping generalizations that go along with them - party-hearty Mykonos, romantic Santorini, boho Antiparos, foodie Sifnos, family-friendly Paros - so spending time exploring them all before choosing a favorite is the way to do it. Below, we've outlined a few of our favorite properties on each island, but we also love exploring the area by yacht, which allows for visits to smaller siblings like Folegandros and Koufonisi, specks of land that make up in charm what they lack in hotels.
Mykonos
Bumping beach clubs, late nights, and beautiful people, Mykonos is great for friends and couples who want sun-soaked days that roll seamlessly into a scene.
Kalesma Mykonos
In the hilltop town of Aleomandra, Kalesma offers a different perspective of buzzy Mykonos. The design-focused hotel, which debuted in April 2020, stays true to Cycladic minimalism with whitewashed surfaces, bougainvillea-draped archways, and locally sourced textiles, but there’s also a sense of worldly sophistication at this chic, grown-up retreat.
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Santa Marina, a Luxury Collection Resort, Mykonos
The most comprehensive and polished retreat on Mykonos, Santa Marina is located about a mile outside of the main town on a secluded peninsula. There are sea views from every room and a private beach, which is protected from the winds. It's a perfect place for families who want to be near the action, with every amenity at their disposal.
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New Openings: Four Seasons Mykonos
When it opened this June, the first Four Seasons on a Greek island upped the hotel game across the country, and its location on the south coast promises to shake up the center of gravity on the island itself as well. View the hotel
Paros
You'll hear people say that Paros is what Mykonos used to be, but we appreciate its charms without comparison. Come for beautiful villages and the sort of tavernas where you're a local by the time your main course arrives.
Cosme Hotel Paros
Cosme is a perfect home base from which to explore the Goldilocks of the Cyclades. Inspired by village architecture, the minimalist interiors open to private pools or expansive sea views, and the hotel showcases Greek art and houses a delightful shop. Beyond the hotel, the cafes and nightlife of Naousa are just ten minutes' walk.
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Avant Mar
Owned by the same real estate company as One&Only Aesthesis and Amanzoe, the 2023 opening of Avant Mar signaled a boost of glitz for Paros (and yes, it has a Matsuhisa.) Rooms, which will appeal to minimalists, are sleek, bright, and breezy, with marble accent walls, and the waves lap Piperi beach just feet away.
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Antiparos
Paros’s cooler, quieter little sister (and neighbor to the southwest), Antiparos is a riot of bougainvillea in the summer. Come to unwind, stay to run into Tom Hanks at lunch.
The Rooster
A few steps from Livadia Beach, this earth-toned resort seems to blend with the landscape, heavily employing stone, wood, and natural fabrics in the decor of its 17 freestanding villas. Guests spend their days lounging by private plunge pools, practicing yoga, and visiting The Rooster's organic garden, where the property hosts private farm-to-fork dinners.
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Beach House Antiparos
This nine-room Antiparos gem is all pared-back Cycladic chic, with cool cement floors and Parian-marble baths. On-site: a sunlounger-lined beach, garden play area, paddleboards, outdoor gym, and access to sister stay The Rooster’s facilities and House of Healing (including the sauna, hammam, small pool). Book top-floor rooms for Aegean views.
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Sifnos
Understated and soulful, Sifnos is famous for food, pottery, and pretty hiking trails. The island has ten individually numbered taxis - that's it - so it's a perfect place for taking things slow.
Verina Astra Hotel
NOS Hotel & Villas
Much like the island itself, the beauty of Verina Astra lies in its simplicity. There's nothing flashy about this 14-room property, which sits high above the dramatic cove of Poulati. Rooms are dressed in simple earth tones and Cycladic whites provided mesmerizing contrasts with the bright blue sea below, and the distant sound of goat bells and the steady rhythm of cicadas provide a gentle soundtrack.
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NOS feels like a miniature Sifnian village: four stone buildings, cobbled paths, mulberry shade, wildflowers, and local pottery woven throughout. There are 18 bright suites, many with private or plunge pools; book a Junior Suite for chapel-peeking at one of the islands hundreds of churches. Days orbit the pool and Faros Beach, and nights end with Athinagoras Kostakos’s cooking.
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Santorini
You've seen the caldera views (and the pictures of hordes of tourists), but if the tumbling architecture of Santorini still beckons, there are ways to do it right.
Katikies Santorini
Canaves Epitome
Canaves Oia Epitome is the antidote to the Santorini scrum, set a mile north above Ammoudi Bay, facing the open sea. The Chaidemenos family’s fourth property, which opened in 2018, has 24 low, volcanic-stone villas that melt into the rock, all sky, pool, and horizon. Plus, smoke-hued interiors, ebony-edged bathrooms, lamp-lit courtyards and heated plunge pools in every room.
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On Santorini, the view is the whole point, and Katikies delivers it in full cinema from its pool deck, suspended above the volcanic caldera and the ink-blue Aegean beyond. A gleaming white, modernist riff on a traditional cliff dwelling, it cascades down Oia’s hillside like a postcard brought to life. The stairs are a workout, so stay in for dinner at rooftop Ellinikon and the on-site spa.
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Food is one of the major highlights of a Greek itinerary, so choosing favorites is nearly impossible - but think of these as a jumping off point for your culinary adventure across the islands.
Alemagou on Mykonos
You'll feel like you're on the Baja Peninsula at this beach club, where windswept rattans and thatched palapas more closely resemble a Mexican resort than a Myconian beach club. Don't miss the sunset!
Ammoudi Fish Tavern on Santorini
On the menu of this happy tavera on the red rocks of Oia, you'll find a lengthy list of freshly caught fish, ordered whole. Choose a sampling of what's fresh and add some mezze to share.
Captain Pipinos Seafood Taverna on Antiparos
Captain Pipinos is all about unfussy charm, with the sound of waves just steps away. The menu is a love letter to the sea: ultra-fresh fish, grilled octopus, and just-caught shellfish, simply prepared.
Omega 3 on Sifnos
Not many people go to Sifnos. Anyone who does will tell you to go to Omega 3. This tiny beach shack may not look like much, but it excels at seafood-centric small plates you won't find anywhere else. Try the citrusy sea bream ceviche and Brazilian-inspired pao de queijo.
Remezzo on Mykonos
It's not often that good food and fun nightlife can be found in the same place in Mykonos, but Remezzo is a longtime exception. Come for a sunset dinner and stay until late-night, this place never disappoints.
Rizes on Mykonos
A family-owned farmstead committed to upholding the strong traditional roots of Myconian customs, Rizes is an experiential destination, where visitors can learn about local folklore, participate in artisanal workshops, and enjoy homemade cuisine.
Siparos Seaside Restaurant on Paros
Lanterns hang from tamarisk trees, whole sea bass is cooked in a salt crust, the sun is setting over the water, and everyone's tan. Could be heaven or could just be dinner at Siparos.
As befits the birthplace of western culture, it's easy to pair Greece thematically and logistically. Whether you're someone who travels for food, history, art and architecture, or the scene, Greece has got it.
The Greek Sampler
After time in Athens, dip down to Paros and Sifnos for low-key island time; finish with a few glam nights channeling your inner Zeus at Amanzoe.
The Classicist
The Romans and the Greeks are paired together in museums all over the world. We think they belong next to each other in your passport, too. A Naples to Santorini non-stop flight makes Rome - Amalfi Coast - Santorini - Antiparos possible.
Beach Babe
Who needs cities? If summer means beach clubs and beach clubs only, a Nice to Mykonos non-stop means you can have lunch in St. Tropez and party the night away on the stone streets of the chora.
