How to Have the Perfect Island Vacation in Greece

Courtesy of Anemomilos Apartments

By Emily Mathieson Posted June 16, 2016

Take an amazing trip to the Mediterranean.

This article originally appeared on

The Aegean island of the moment seems to change every summer. We’ve uncovered this year’s must-know isles—along with how to get there, where to stay, and, of course, what to Instagram.


The ongoing search for quiet hangouts has led intellectuals and history buffs to Sími, where there's been an uptick in colorful hotels.

Getting There
Fly in to Rhodes (there are nonstop flights from multiple European cities), then take a one-hour express ferry.

Home Base
The atmospheric Old Markets hotel (doubles from $942) is a registered national monument with 10 antique-filled suites.

Photo Op
Travel specialist Elena Papanicolaou of Fly Me to the Moon recommends hiking up to the top of the old town of Horio to see the crumbling remnants of a castle built by the Knights of St. John.


The bohemian and fashion sets (Leonard Cohen, Chloë Sevigny) have alighted here, joining forces to create a happening art scene.

Getting There
Take a two-hour hydrofoil from Piraeus, which is only a 20-minute drive from Athens.

Home Base
Hydra is either about simple, charming guesthouses like Orloff (doubles from $160) and Cotommatae Hydra 1810 (doubles from $181) or villa rentals. Five Star Greece can help.

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The Deste Foundation, a cutting-edge gallery in a former slaughterhouse, is a must-visit.

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Despite its great beaches, easy access, and a variety of watersports, Páros remains off the radar—which is why families head here to avoid the crowds.

Getting There
Take a 40-minute flight from Athens or a three- to four-hour boat ride from Piraeus.

Home Base
Páros has plenty of hotels, but big broods are better off spreading out in a villa. White Key Villas offers all types of rentals, including the brand-new, five-bedroom Villa Iro (groups of 10 from $15,146 per week).

Photo Op
Look out for the weathered blue furniture spilling from low-key tavernas to the water’s edge in the harbor.


Thanks to an increase in nonstop flights to neighboring Santorini, this unsung Cycladic island is on the verge of wider discovery.

Getting There
Fly to Santorini, then take a 90-minute ferry (between May and October); or take a four-hour ferry (year-round) from Piraeus.

Home Base
The simple but lovely Anemomilos apartments (doubles from $281) have sensational views thanks to their cliff-clinging setting.

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Local fashion designer Christina Economou suggests hiking up to the church of Panagia. It’s the island’s biggest religious building, and it looks out across the archipelago.


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