Built atop steep cliffs some 1,000 feet above the Aegean Sea, the villages and towns of Santorini seem like places that shouldn’t exist. That only adds to their romantic allure. The port, whose official name is Skala, is at sea level of course, in the capital of Fira, which means that getting to most of the sites will require a car or a very ambitious uphill walk.
What We Love
Whitewashed Architecture: Santorini is arguably the prettiest of the Greek Islands, and the blue roofs topping white buildings create postcard-perfect Aegean images.
Greece’s Best Wines: The white Assyrtiko grape makes a crisp, pleasantly saline wine. Sample it at the tasting room of Domaine Sigalis or Gaia, which is directly on the beach. Also try the sweet wine called Vinsanto, which is excellent for dessert.
Best Known For
The Caldera: Santorini’s striking geography is the result of a volcanic explosion that turned a roundish island into a crescent. See the caldera up close with a boat trip to the tiny, wild, black and red lava-rock island of Nea Kameni in the center.
Oia: No trip to the Greek islands is complete without watching the sun set over Oia, the most picturesque, charming village on the island. Follow the pack to the point for the best photo of the old-fashioned windmill and Technicolor sky behind it.
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Who It's Best For
Sun (Not Sand) Lovers: Santorini isn’t known for its beaches (and the dark volcanic sand can get blazing hot), so sunbathing typically happens poolside at day clubs or hotel restaurants.
Romantics: It’s hard to ignore the sensuality here. Santorini is an island you want to share with a loved one.
Don't Say We Didn't Warn You
Steep Cobblestone Streets: Do not mess around with so-so shoes (and forget about heels).
The Financial Crisis Isn’t Entirely Over: The EU pulled Greece back from the brink, but the economy still isn’t exactly rock-solid. It can’t hurt to have more cash than you might usually bring.
Ann Abel is a Brooklyn-based contributor to ShermansCruise who has also written for Departures.