Santorini, Greece

Santorini is really a volcanic caldera rim: the island's white-and-blue villages, Oia and Fira chief among them, sit on cliffs above the flooded crater left by one of the largest eruptions in recorded history. That geography is also why the sunset views are famous — Oia's western-facing caldera edge gets crowded well before sunset in peak season, so we book dinner reservations that hold a table through the show rather than leaving it to chance.

There's no nonstop flight from the US to Santorini itself. The route runs through Athens: a nonstop flight from most East Coast gateways, then either a 45-minute domestic flight or a faster high-speed ferry (around five hours) on to Santorini's port. We build in at least one buffer night in Athens on the way out, since a missed connection here means a missed hotel night, not just a missed flight.

July and August bring the best weather but also the highest hotel rates and the thickest crowds on Oia's caldera path. Late May through June, or September into early October, get the same blue-and-white photographs with noticeably shorter lines and lower prices — that's the window we steer most couples toward.

The caldera views that define Santorini's reputation are concentrated in Oia and Fira, both built along the rim of what's actually a collapsed volcanic crater — the black, red and white sand beaches on the island's other side are the visible result of the same eruption. Ferry connections link Santorini to Mykonos and the rest of the Cyclades easily, so a multi-island Greek itinerary is straightforward to build around it, and the island's small size means a rental ATV or car covers everything in a day or two.

Three to four nights covers the island itself comfortably, and it's most often booked as one stop within a longer Greek islands itinerary rather than alone. It suits couples and honeymooners specifically — the island's appeal is heavily built around its views and romantic atmosphere rather than activities for families or groups.

Getting there: About 13h from US East Coast gateways, via a nonstop to Athens plus a short domestic hop. Voldeluxe compares routing and cabin options for Santorini, Greece rather than booking the first itinerary a search engine surfaces, and times the trip against Late May to June, or September to early October rather than whatever dates happen to be cheapest.

The eruption that created Santorini's caldera, dated to roughly 1600 BC, was one of the largest volcanic events in recorded human history — powerful enough that some historians connect it to the Atlantis legend and to disruptions recorded in ancient Egyptian records thousands of miles away. Akrotiri, a Minoan Bronze Age settlement buried under volcanic ash on the island's south coast, was preserved so completely by that eruption that it's often called the 'Greek Pompeii'; unlike Pompeii, though, no human remains have been found, suggesting residents had warning and evacuated. Santorini's volcanic soil, meanwhile, turned out to be extraordinary for wine: the indigenous Assyrtiko grape grows in low, basket-shaped vines woven close to the ground to protect them from the island's constant wind, a training method found almost nowhere else, and the resulting wines carry a distinct mineral, saline character that wine critics specifically attribute to that volcanic terroir. Fava, a yellow split-pea puree grown on the island and unrelated to the Italian fava bean despite the name, is the dish locals point to as genuinely Santorini's own — worth ordering over the more generic Greek-taverna staples found on every island in the Cyclades.