The Cyclades

Instead of people, the tiny island of Despotiko is populated by...goats. In fact, there are about a thousand of them. There are also ancient ruins, and archaeologists come here to churn up centuries-old offerings to Apollo and Artemis—vases, agricultural tools, and figurines. Maybe there’s no one living here today, but Despotiko has plenty of past: It played host to the Venetians, Ottomans, and many, many pirates. Aside from millennia of ruins, the views of Folegandros, Syros, and Sifnos are spectacular. Getting to Despotiko is a breeze, especially from Antiparos, where the ferry only takes a couple of minutes.

Spending early mornings or late evenings on long, meandering hikes around Paros is one of the most memorable parts of a visit. Cape Korakas lighthouse, built in 1887, is at the end of one of these trails and acts as a visual reward for your cardiovascular labors. The trail leading up to it is framed by spectacular rock formations, as well as steep slopes leading down to hidden beaches and coves. Image courtesy of paroshikes.com.

Hike down the steps to Ammoudi Bay at Oía’s port to find a pristine swimming area lined with family-owned tavernas. Ammoudi is the best of them, especially for the small plates, like the fresh anchovies marinated in vinegar, salmon tartare, and prawns with ouzo and orange. The view is basically dinner theater, as sailboats and fishing vessels make their way back and forth across the water as the sun goes down.

The location in Oia is a big selling point for Katikies Kirini Santorini, 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.

A staple on the island since 1922, Aktaion is the place to feel cozy and familial. The menu makes use of the best local ingredients to serve up all the classic Greek hits (the moussaka, vegetable fritters, and homemade pasta are all outstanding). Make a reservation and ask for a table outside so you can watch the sun set over the Caldera.

You can easily spend an entire afternoon at Scorpios, a beach club on the southern tip of the island. Reserve a sun bed and slowly make your way through the (predominantly vegetarian) lunch menu. The food is deservedly known as some of the best on Mykonos and includes big plates of wood-fired peppers, zucchini, and endive, along with all manner of salads. When the sun goes down, the whole place turns into a boho-chic dance party.

There’s no telephone, electricity, or Wi-Fi at this bare-bones taverna near Agios Sostis Beach, and that’s exactly the appeal. Nothing distracts from the unobstructed coastal views and the simply, perfectly prepared plates of grilled octopus, prawns, and chicken and super fresh Greek salads and artichokes kissed with lemon juice. Kiki’s is technically open only for lunch, but service lasts until early evening for those who’ve gotten a late start.

A jet-set hangout since the ’60s, Remezzo feels a little more refined than the average Cycladic taverna, with food to match. Even simple entrées are elaborately plated and colorful, like raw vegetable carpaccio with honey and citrus vinaigrette and roasted scallops with Aegean salt, sweet artichoke mousse, and Greek truffle. And the house rosé is great, which means you don’t have to spend a fortune on wine.

Run by the same family for three generations, Nikolas is as local as it gets on Mykonos. All the vegetables and most of the meat comes from the family’s nearby farm, and Nikolas (the grandson of the original owners) catches the fish for the same-day dinner service. Tables are wedged right into the sand of Anna Agia beach, at the southern end of the island, but shaded patio and indoor seating is available, too, for those summer scorchers.