Santorini

The postcard image of Santorini — whitewashed buildings stacked along a curved cliff edge, blue domes catching the light — is a photo of a volcanic crater rim, not a coastline in the usual sense. Around 1600 BC, an eruption believed to be one of the largest in recorded history collapsed the center of what was once a much larger island, leaving behind the caldera that Santorini's towns now cling to the edge of. The volcano isn't extinct either; a small island in the middle of the caldera, Nea Kameni, still shows activity, and boat tours will take you to walk on it.

Oia gets the reputation and the crowds, largely for its sunset — genuinely one of the better ones in the Mediterranean, with the light hitting the caldera cliffs at an angle that turns the whole town gold for a few minutes. The problem is that everyone knows this, and the main viewpoint near Oia's castle ruins fills in dramatically an hour or more before sunset in July and August. Walking 10-15 minutes further along the coastal path, away from the single most-photographed spot, gets a comparable view with a fraction of the crowd.

Fira, the island's main town and transit hub, is busier and less photogenic than Oia but noticeably cheaper to stay in, and it's a reasonable base if the caldera-view premium in Oia doesn't fit the budget. The walking path between the two towns runs along the caldera rim for several hours and is one of the better free activities on the island, weather and stamina permitting.

The volcanic soil that makes the island geologically unstable also makes it unusually good for wine. Santorini's vineyards grow Assyrtiko grapes in low, basket-shaped vines trained close to the ground to protect them from the island's strong winds, rooted in volcanic ash that retains moisture in a way regular soil doesn't. The resulting wine is mineral and dry, distinct enough from mainland Greek wine that a tasting is worth building into the trip even for visitors who don't usually seek out wine tourism.

Getting around requires more planning than a well-connected European city. Public buses link the main towns but run a limited schedule, and most visitors rent an ATV or small car to reach the volcanic beaches — Red Beach's cliffs, Kamari's black sand — on their own timeline rather than working around bus departures.