The Best Things to Do in the Greek Islands

The elemental drama of Santorini’s volcanic landscape draws more than 2 million visitors every year. For more than 3,500 years, this mineral-rich terroir has also produced outstanding wines. There are around 50 indigenous grapes (notably the bone-dry assyrtiko, key for producing the amber, caramel vinsanto). The vines are coiled around the grapes like baskets to protect them from the fierce sunlight and meltemi winds. Santorini Wine Trails offers personalized, small-group wine tours run by an enthusiastic and erudite enologist, Iliana Sidiropoulou. Ask her to take you to Domaine Sigalas, where award-winning vintages are paired with superb snacks; to Gaia, located in an old tomato-canning factory on Monolithos beach; and to the Venetsanos winery, whose rooftop wine bar seems to float above the port of Athinios.

Santorini’s flooded caldera hogs the headlines, but the smoldering crater on Nisyros is equally dramatic. In fact, this entire Dodecanese island is an active volcano, with a 2.5-mile caldera surrounded by several smaller craters. Although the volcano hasn’t erupted since 1888, hot puffs of steam hiss as you tread gingerly across Stefanos’s crackling yellow surface. If you can’t stand the sulfurous stink, the adorable village of Nikia dangling above the volcano offers excellent aerial photo opportunities. The village school has been converted into the Volcanological Museum, with 3-D models and videos explaining the big bang that created Nisyros 24,000 years ago. Afterward, stop at Nikolas’s kafenio in Porta, a miniature pebbled piazza painted with geometric patterns, for an ouzo meze.

A retreat for Orthodox pilgrims and publicity-shy celebrities, Patmos owes its mystical aura to the 11th-century Monastery of Saint-John, which dominates the UNESCO-protected settlement of Chora. Follow wafts of incense into the mosaic-paved courtyard, where black-robed monks go about their devotions. Marvel at the religious icons, Byzantine frescoes, and embroidered vestments glimmering in the chapels. The library is a trove of rare manuscripts and books, including a 6th-century copy of St. Mark’s Gospel written in gold and silver script on purple vellum. A short walk downhill is the crepuscular Cave of the Apocalypse, where St. John wrote the Book of Revelations. Light a candle and pray that the end of the world isn’t nigh.

Blame actress Meryl Streep for putting this chapel on the map. Teetering atop an outcrop of rock adrift the northeastern coast of Skopelos, the church of Agios Ioannis tou Kastri (St. John of the Castle) is where Streep serenaded Pierce Brosnan for the movie Mamma Mia! (and where her on-screen daughter, played by Amanda Seyfried, tied the knot). This has inevitably generated a stream of inappropriately attired ABBA fans, eager to climb the 200-odd stairs to the church. But come in the early evening, and you might have the place to yourself. Just don’t plan a wedding here unless you are Greek Orthodox and intend to invite no more than half a dozen guests (the spartan interior is tiny).

The ancient Greeks called Folegandros “iron hard,” but this Cycladic island has a mellow soul beneath its edges. The northern part is the wildest, where locals still scrabble a living making cheese from their goats, threshing grain with mules, and fishing off translucent bays. At homestead tavernas (like Eirini’s grocery-cum-eatery in Ano Meria), the owners rear or grow everything they serve. The main village, Chora, is huddled on a cliff 650 feet above the sea, but the emerald water below is so clear you can count the fish swimming by. The tangle of lanes all lead to three interlocked squares lined with tavernas and bite-size bars, where evenings drift by as you drink shots of rakomelo (warm grappa with honey).

Wearing a simple caftan with fine gold embroidery, studded sandals, and no makeup, Kiki Sinteli is effortlessly chic. She’s also the best advertisement for her boutique in the handsome Chora of Andros, a lush island with an abundance of shipowners. Sinteli designs most of the wares herself: A-line skirts with ancient Greek motifs, Liberty print tunics, paisley shirtdresses, and soft leather sandals. She has also assembled an exquisite collection of accessories made by friends or collected on her travels, including jewelry by Greek designers Lito and Marianna Petridi, bright tassel necklaces, and pastel-striped sarongs. That’s your summer wardrobe and souvenir shopping sorted. (+30 22820 23685)

Huge, lush, and kept hush-hush by the local shipping families, Andros is only two hours by ferry from Athens. The main town, with its neoclassical mansions, fine-art museums, and yacht club, is more Downton Abbey than Aegean village. The mountainous interior is another world—all rushing streams and springs, waterfalls and wetlands, with 84 villages hidden in the valleys and forests. This unexpected wonderland is now accessible thanks to Andros Routes, a grassroots initiative to clear and waymark the 186 miles of ancient footpaths that crisscross the island. To date, volunteers have opened up 20 paths, including the Andros Trail, a continuous 62-mile path that straddles the whole island.

Although Lefkada is the only Greek island accessible by land (via a causeway first built in 500 B.C.E.), its main attractions are the incredible white-sand beaches Porto Katsiki, Kathisma, and Egremni, which are featured on countless Greek tourism posters. The annual Ionian Regatta starts in Nydri’s marina. Mild winds and a smattering of small islands with plenty of anchorages make this part of the Ionian ideal for inexperienced sailors. Strong gusts in the northern part of the island are a favorite among kitesurfers (who swoop above Agios Ioannis beach) and windsurfers (who whiz across Vassiliki Bay).

The ancient historian Herodotus described Naxos as the “happiest of islands.” It’s certainly hard not to have a good time on the largest of the Cycladic islands, with its antiquities, medieval watchtowers, mountain trails dotted with Byzantine churches, and miles and miles of soft, sandy beaches. Hidden in the hills are three marble kouroi―giant anthropomorphic statues measuring more than 35 feet long. Nobody knows why these 2,500-year-old statues were built or how they ended up there. Two of them lie snoozing in a shady lemon and oleander grove near Melanes. The third, unfinished kouros has been lying in a marble quarry near the seaside village of Apollonas since the 6th century B.C.E.

A bit removed from the other Sporades islands, Skyros is deeply traditional. Old ladies in yellow headscarves sit on their stoops, bent over embroidery. Carpenters chisel the distinctive wooden skamnaki (miniature chairs carved with geometric patterns) in dusty workshops. Beaten copper and painted ceramic plates decorate every inch of wall in typical village houses. If you peek inside, weathered residents will usually invite you in for a Greek coffee. Otherwise head to the Manos Faltaits Folk Art Museum, which contains a replica Skyros house, as well as Byzantine manuscripts, farm tools, and the intricate folk costumes that locals still wear for weddings and church festivals. On a terraced hillside overlooking the sea, the adjacent amphitheater is a glorious setting for summer concerts.

Of all the Greek islands, sybaritic Mykonos has the most to offer big spenders. Instead of worry beads and flip-flops, the shopping scene is more Louis Vuitton and Lalaounis jewelry. Ergon, a stark white concept store with rag rugs installed between the rafters, stocks an exciting collection of clothing and accessories by Greek designers. Embroidered caftans, tasseled espadrilles, and colorful straw fedoras are just the thing for sashaying through town or showing off your tan at beach bars such as Alemàgou and Scorpios. Gifts inspired by ancient Greece include a Trojan horse paperweight, a minimalist amphora pendant, and gold olive-branch earrings. You can also customize your own espadrilles, T-shirt, or beach tote.

Dreamed up by a pair of American philosophy majors, this atmospheric bookshop a few steps down from Oia’s pedestrian “main street” is packed to the rafters with novels, travel books, rare first editions, and, of course, Greek mythology and philosophy. (Look up, and squeezed between the rafters and bookshelves, you’ll see bunks where employees bed down after closing time.) The easygoing, erudite staff and the soundtrack of Nina Simone and Ella Fitzgerald make it hard to leave in a hurry (or empty-handed). Journals and totes imprinted with Greek quotes make great souvenirs. The foldout map of Santorini, highlighting the owners’ secret swimming spots and watering holes, is all you need for an authentic experience of this most touristy of Greek islands.

Locals claim there are 75 beaches on volcanic Milos, ranging from brilliant white to black, red, and gray. Hidden fjords, hot springs, and underwater caves make a stunning setting for kayaking, scuba diving, and sailing. The otherworldly coastline is also a refuge for monk seals. If you’re lucky, you might spot some as you swim through Kleftiko, a series of white rock formations eroded by the piercingly blue sea. Pirates used to lurk in the caves, waiting to capsize ships. A round-the-island boat trip includes a swim through Sikia Cave, where sunbeams bounce off the cobalt water and mineral deposits cause rainbows to ripple across the rocks.

Hozoviotissa Monastery was built in 1017 C.E. as a feat of sheer willpower. It’s hard to fathom how the eight-story building was carved from the cliff face, 984 feet above the sea. It’s a spectacular hike, up hundreds of steps to an entrance so low and narrow, you literally have to bow down before God. In the chapel, dazzling silver-plated icons and clouds of incense leave you feeling light-headed, especially as you emerge onto a tiny balcony floating between sky and sea. In the 18th century, 100 monks lived there; now there are only three. Dress modestly and go early to beat the heat and crowds—ideally for the morning liturgy, which starts at 4 a.m., to watch the sunrise from what feels like heaven.

Mastic—the fragrant resin cultivated exclusively on southern Chios—gives local cuisine a distinctive flavor. Used in everything from cakes to liqueur, mastic has been the mainstay of the local economy since the Middle Ages. The masticohoria (mastic-producing villages) were fortified with walls and watchtowers to protect supplies of this precious resin from pirates and smugglers. Unchanged since Byzantine times, the village of Mesta is dominated by a medieval tower from which you can look out across the town. Walk along the walls and rooftops or get lost in the maze of cobbled lanes, deliberately designed to confuse outsiders. In Pyrgi, all the houses are completely covered with black-and-white geometric patterns, an equally disorienting spectacle.

There’s only one proper road on Asytpalea, the westernmost island in the Dodecanese, and even that peters out in the middle of nowhere. Dirt tracks lead to isolated pebble beaches such as Vatses and Kaminakia. (In Kaminakia, stop by Linda’s for farm-to-table fare that includes an excellent lemony goat stew and stuffed vine leaves.) It’s a lovely hike from the Monastery of Agios Ioannis—the most sublime spot for sunset—through a lush ravine to a deserted cove. To really get away from it all, take one of the wooden boats from Pera Gialos to Koutsomiti and Kounoupes, two tiny islands connected by a double-sided beach with fluorescent turquoise waters. Locals go there to collect rock salt after a windy day.

Ouzo is produced primarily on the Greek island of Lesvos. The lively neoclassical port of Mytilene is awash with delightful ouzeries that offer dozens of varieties of the liqueur alongside saucers of salted sardines, cheese cured in olive oil, and crinkly olives. Running parallel to the harbor is pedestrian Ermou, the market street where you can stock up on all kinds of local delicacies. Squeezed in among the spice shops, cheese emporiums, fishmongers, and butchers decorated with garlands of spicy sausage are tiny time-warp shops selling buttons, embroidery, or bric-a-brac. At the north end of Ermou is Kafeneion O Ermis, a landmark restaurant run by the same family since 1922, where the ouzo mezes are a cut above: stuffed zucchini flowers, octopus braised in wine, and marinated anchovies.

Craggy, car-free, cosmopolitan Hydra has always been an island of artists. Brice Marden, Juergen Teller, and Adam Cohen (son of Leonard) all have homes here. The Athens School of Fine Arts runs a summer residence program in a vast mansion that once belonged to a famous admiral. (It’s closed to the public, but if you can sneak in, you’ll find a wonderful collection of 19th-century nautical paintings.) Up-and-coming artists and heavyweight collectors head to Hydra every summer to check out the boundary-pushing exhibits at the Hydra Workshop, a former ship-repair yard on the waterfront; the Hydra School Projects, which shows established and emerging artists in the village high school; and the DESTE Foundation’s site-specific installations, located in an abandoned slaughterhouse.

When you arrive in Corfu, you may notice it doesn’t look a great deal like the other Greek islands—in fact, it has a distinctly Venetian feel. That’s because, unlike the rest of Greece, Corfu was never ruled by the Ottomans. The Old Town is a perfectly preserved Venetian town and a UNESCO World Heritage site. Renaissance, baroque, and classical touches can be found between every alleyway and square. Some points of interest: the Old Fortress, Spianada (the largest square in the Balkans), and the Liston (an arcaded promenade where wealthy aristocrats used to gather).

Part of the Cyclades, this Mediterranean retreat is complete with white beaches and crystal blue waters, pottery making that dates back thousands of years, and villages that uphold ancient traditions. But what really makes this island stand out from the rest is a historic culinary scene that continues to thrive. Sifnos is the birthplace of the first Greek cookbook, written in 1910 by chef Nicholas Tselementes. Over the years, celebrity Greek chefs have opened up restaurants next to local eateries whipping up traditional dishes, from mastélo (goat or lamb cooked in red wine) to chickpea balls flavored with herbs.