Two things are certain in Santorini: One, it will far exceed your expectations gathered from guidebooks pre-trip. And two, you won’t be there alone. This cliff-side sprawl beckons personal yachts and meager cruise ships in from the Aegean Sea to dock adjacent its surreal landscape formed from a volcanic eruption that sunk the center of the island and formed imposing cliffs alongside. Once on land, you’re in for a dazzling display of white-stone houses precariously perched from their lofty viewpoints, blue-domed buildings seemingly capable of tumbling into the sea at any moment, and a blood-red beach speckled with the tops of sun-seekers’ umbrellas. Famed for its eerily beautiful sunsets, Santorini’s escapades don’t stop once the sun drops. Find a quaint café or candlelit table on the caldera’s edge and sip vino until the last speck of rays disappears, offering relief to your suntan. In the morning, repeat.