There are around 6,000 islands in Greece; around 227 are inhabited, and around 225 are not Mykonos or Santorini. You really can’t go wrong with any place you pick (if you can dodge the Surf Lodge defectors and 80€ beach chairs, parts of Mykonos are quite beautiful), but if you’re looking for something a little quieter and less-trodden, you have options. Too many options, even. I’m a mainland Greek, but I’ve been making a concerted effort to tick off new islands each time I’m back in the country… and even so, I’m only at 30. I have a lot of work to do.
In the meantime, I’ve amassed a list of personal favorites. Some are lively, with stylish boutique hotel openings that draw a trendy crowd; the very best ones, in my opinion, are laid-back, too unpolished for TikTok, and probably a bit of a pain to get to. These are the spots where the taverna menus are hand-written, or don’t exist at all, and no one has heard of an espresso martini. The below three are only a snapshot—and some are admittedly more under-the-radar than others—but if you’re planning a trip to Greece this summer and want something away from the crowds, these are the islands to look at. As for the rest? We both have time.
Courtesy of Elly Leavitt
Astypalaia
From above, it looks like Mars. Arid terrain accessorized with rocky coves, wild mountains, and dramatic shorelines; a concentrated burst of white cubist homes signals life (and the main town). The “Butterfly of the Aegean,” so called because of its shape, is a far cry from the glittering, developed islands in the neighboring Cyclades, and that’s exactly what’s so special about it. Astypalaia is a place where people will offer you a ride if you look too forlorn on your uphill walk home; where locals congregate for impromptu bouzouki concerts in alleyways; where the best beaches are reached via a slightly treacherous route carved into the side of a mountain that is, technically, “a path,” but is, more accurately, just the side of a mountain.
A car or an ATV is recommended to see the wildest parts of the island (though the AstyBus, an electric ride-share option that exemplifies the island’s commitment to sustainability, is helpful for getting around), so much of the life is concentrated in Chora. After hiking up to the castle to watch the sun go down over the sea (perhaps making a pit stop at Castro Bar for an aperitivo on your way up), go for a late dinner at Kafeneio Karai or Apanemia, and order what seems like too much food (it’s all good) to share. For a day trip, I booked a last-minute boat ride to Kounoupa and Koutsomiti, two uninhabited islets with the clearest water I’ve ever seen—there’s so much to explore on this deceptively quiet island. I first went a few years ago, and am already planning a return this summer.
Where to Stay: Chora is really your best bet for accommodation—you’ll be within walking distance of all the markets, coffee shops, and bakeries. This home, just opposite the castle’s entrance, puts you in the middle of it all (including the best gyro on the island, at To Steki tou Kalofaga, which is just a few minutes away). It’s neat, full of traditional island charm, and even has a little patio where you can take your coffee each morning; the perfect cozy home base.
Courtesy of Elly Leavitt
