Santorini punishes the people who arrive at the wrong hour and rewards the ones who plan around the ships. This is that plan, set down plainly: the winery on the cliff, the ruined city on the ridge, the sunset that has no bus behind it, the table where the island still cooks for itself, and the practical things nobody tells you until it is too late. Twenty-five entries, each one chosen because it earns the detour. The first five are below, free. The rest is a short guide you can carry in your pocket.
Free, the first five
01 – 05 of 25
01
Time it
Oia, timed around the ships
Oia is not ruined, it is only mistimed. The crush is the middle of the day, roughly eleven to four, when the cruise passengers are bussed up from the port in one wave and the marble lanes seize solid. Come at first light instead, before about ten, when the blue domes and the caldera are yours and the shops are only lifting their shutters. Or come back in the last hour before sunset, once the ships have sailed and the day groups are already gone, and take the light from a low wall away from the famous castle terrace, where the whole village presses in for the photograph. The middle of the day is for a shaded lunch in a quieter village, not for standing in a queue on a cliff.
The move Two windows only: in Oia before ten, or after the ships leave. Check the day's cruise schedule online before you set your alarm, and skip the castle terrace at sunset for a wall further along the path.
Map Oia
02
Drink
The gravity winery above the port
On the cliff above Athinios, the ferry port, in Megalochori, Venetsanos was the island's first proper winery, built in 1947 and cut into the rock on four levels so the wine ran downhill by gravity in a place that had no electricity. It was brought back by the family and reopened after a long restoration, and it now pours mostly Assyrtiko and Mandilaria on an open terrace that looks straight down onto the boats and out across the caldera. It is one of the few places on Santorini where the wine, the view and the history sit in the same glass, and it is a short drive from Fira rather than a scrum in a village lane.
The move Book the tasting for late afternoon, take the short guided walk through the old cellars first, then hold the terrace for the light going down over the port. A driver is easier here than parking.
Map Venetsanos Winery
03
See
The ruined city on the ridge
Everyone climbs for the sunset and almost nobody climbs for this. High on the Mesa Vouno ridge between Kamari and Perissa, Ancient Thera is the old city of the island, Greek and then Roman, its streets, agora, theatre and terraces still laid out along the spine of the rock hundreds of metres above two beaches. The reward is as much the position as the stones, the wind, the drop on both sides, the whole south of the island under you. It opens in the morning and closes by mid-afternoon and it is closed one day a week, so it is not somewhere to leave until the last minute of a hot afternoon.
The move Go early, from the Kamari side, and take water and a hat, there is no shade on the ridge. Check the current hours before you set out, it shuts by mid-afternoon and one day a week entirely.
Map Ancient Thera
04
The rule
Sort your driver before you land
Taxis on Santorini are few and expensive, a small fleet for a whole island that fills to bursting in summer, and they do not run on a meter, so you agree the fare before you get in or you pay whatever is asked at the door. On a bad day you can wait half an hour at the port or the airport rank for a car that never comes. Book a private transfer or a driver ahead of time, and shop the price rather than take the first quote, the difference between companies is real. Do not leave it to the hotel to conjure a car at the last minute on a busy evening, because that is exactly when there are none.
The move Arrange your airport and port transfers before you travel, agree the flat fare in writing, and keep one trusted driver's number for the trip. For a day of villages, a half-day hire with a driver often costs less than three separate taxis.
Map Athinios ferry port
05
See
The sunset that isn't Oia
The finest place to watch the sun go down is not in Oia at all, it is the walk out to Skaros Rock below Imerovigli. A path drops from the village, past the last hotels, onto the bare promontory that once held a Venetian fort, and around its far side a tiny chapel, Theoskepasti, sits alone above the water with the whole caldera opening in front of it. It is a proper twenty-minute scramble each way on loose ground, which is exactly why the crowd that fills Oia never comes, and you get the same sun, the same sea, and the quiet the postcard never mentions.
The move Wear real shoes, there is no railing on the far side, and set off well before the sun so you are on the rock, not still on the path, when it goes. Bring a torch for the walk back up.
Map Skaros Rock