9 Cool Things to Do in Santorini

Sailors who lived in the one-time fishing village of Oia looked to Santorini’s cliffs as a refuge from the sea. It’d almost be a crime to come to Santorini and not sleep in one of the infamous cave homes-turned-hotels dotting the caldera. Our pick: Canaves Oia, whose 17th-century wine cellars have been transformed into a series of chic suites perched above the sea. You won’t need to venture out to catch Santorini’s glowing sunset, either. Just take a seat on your whitewashed patio (or better yet, in your infinity plunge pool) and get ready for the show to start.

The entire island acts as a living museum, but if you’d rather get a hands-on approach to art, swing by the Santorini Arts Factory, a cultural center housed in an old tomato factory on Vlychada Beach. The art here takes on multiple forms, from Medusa-inspired dance performances to contemporary Greek exhibits and sewing seminars. It’s worth the trip alone for the shop, a stylish, well-curated collection of locally designed wares (think porcelain pottery and utilitarian-style totes) handcrafted from materials sourced across the country.

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It’s easy to write off Santorini’s boutiques as souvenir shops—that is, if you don’t know where to look. Tucked between the cave-like spots selling postcards and paintings are a few of Greece’s best boutiques like Greek-designer-heavy Under a Fig Tree, where you can stock up on geometric-inspired swimwear by Sun.Set.Go or snag a pair of plastic and wood hybrid sunnies from Extreme Living. If you’re after a more precious keepsake, pop into the iconic Ilias Lalalounis in Fira for glittering, handmade gold jewelry inspired by ancient Greek artifacts. Also in Fira, you’ll come across artwork from Cyprus-born Yorgos Kypris at MATI Art Gallery, where you can snag a piece of art in the form of 18-karat gold fishbone pendants.

On the road leading from Oia to Ammoudi, you’ll come across Katharos Lounge, a hidden beach bar that’s only reachable by foot where fewer crowds spell more room to spread out and soak up the sunset sans slews of tourists. Days easily drift into nights at Sea Side by Notos, on Perivolos Beach, where you can sprawl out on a sun bed or sofa with a glass of Champagne before digging into a decadent meal (cuttlefish ink risotto adorned with gold leaf; nontraditional twists on moussaka blended with shrimp and crab meat) at the boat-turned-table lying on the beach. If you really want your privacy, hole up at Mesa Pigadia by Akro, a restaurant housed in a cave with a series of rustic, thatched umbrellas perfectly placed on the stretch of beach out front.

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We don’t like to play favorites when it comes to Santorini’s beaches, since each one offers up a different vibe (and view). Make the choice yourself while beach hopping along coast in one of the most popular modes of transport: boat. Take your pick between classic caique (traditional wooden fishing boat) with Caldera Boats or private luxury catamaran yacht and set off on the Aegean, where you’ll really see the Atlantis connection. In between mud baths in volcanic hot springs and snorkel sessions off Red Beach, aptly named for its red rocky shores sheltered by cascading rust-colored cliffs, you’ll do a drive-by tour of the time-trapped island of Thirassia and the cliffside monasteries lining Santorini’s coast.

Don’t be swayed by the donkeys slowly trekking up the cliffs from Santorini’s shores. A much better option when it comes to exploring the island’s dramatic landscape is by foot on a hike along the “Caldera’s eyebrow,” or the balcony of Santorini. You’ll be following in the same cobblestoned footsteps as ancient merchants and farmers during the four-hour hike it takes to get from Fira to Oia’s characteristic blue-domed buildings. This is where you’ll get that Insta-worthy shot—particularly when pausing at the tucked-away village of Firostefani (perched on Fira’s highest point) at sunset.

Volcanoes and wine might not sound like a perfect pairing, but Santorini happens to be home to some of the world’s oldest vineyards—and top-notch vino. This isn't Napa Valley, though. Donkeys help farm the hand-picked vineyards dotting the lava-covered land and its basket-shaped vines. Here, you’ll find over a dozen wineries, including beachside Gaia and white-domed Boutari. Pair your tasting of the island’s signature white wine Assyrtiko with a garden-fresh Greek salad lunch at Artemis Karamolegos Winery, whose ingredients are sourced straight from the surrounding fields and whose courtyard looks out to Avis Beach and Anafi island. Curious about these grapes? Get schooled on winemaking (while indulging in additional tastings) at the Art Space Winery; the island’s dedicated wine museum doubles as an art gallery that’s carved into the chambers of an old winery.

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Don’t let the name fool you—some of Santorini’s finest fare is served up in centuries-old taverns. The ones most worth visiting, however, require a bit of work to seek out. Start your food tour at Roka, just off the marble main walk near Oia’s puzzle piece-like streets. Its interior feels like you’re joining a friend at their home for dinner, but the vine-covered pastel patio is our pick for sea views served alongside specialties like Cretan pasta called skioufikta and casserole-style pastitsada, or slow-cooked beef served in fresh tomato sauce. For a gastronomic feast in Oia, take a seat at 1800, an eatery tucked inside a former captain’s house (read: mansion) built during the same century as its name suggests. If you’re debating where to catch the island’s signature fiery sunset, the rooftop garden here wins, hands down. For lunch, hike down the steep path from Oia to Ammoudi Bay’s Ammoudi Fish Tavern, where you can select your seafood of choice from last night’s catch. On the stroll over to Fira’s port, pause for Champagne in one of the capital’s most scenic spots: Tango. The open rooftop lounge carved into the cliffs brings a roster of top-notch DJs for a very Mykonos-type vibe. If your trip happens to fall during a full moon, you’re in luck; this is when summer’s best party is in full swing.

Why island-hop when you’re already on one of Greece’s most gorgeous isles, you ask? Santorini may sport some pretty stunning cave hotels, but wait until you see what’s carved into Iraklia, one of three neighboring islands known as the “pearls of the Aegean.” On Iraklia, you’ll find the largest caves in the Cyclades lined with age-old rock paintings, while over on Koufonisia (favored by the likes of Cavalli and the Missonis), you’ll see charming windmills (you don’t need to make your way to Mykonos for that!) and six beaches all within walking—or biking—distance. As for Donoussa—the most remote of the three—tourism hasn’t quite hit the island in the same way as bustling Santorini, meaning you’ll have untouched sandy shores all to yourself.