Santorini.

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, and at the end, the traps to skip. All of it free to read.

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

06

Eat

The taverna where the island still cooks for itself

The good island food is not on the caldera rail, where you pay for the view and the kitchen coasts. It is inland, in the working villages, where the tavernas cook for the people who live there. Head for Exo Gonia, Vothonas or Pyrgos and eat where the car park holds local plates rather than coaches, at a table under a vine with a handwritten list of the day's dishes. What lands is the island on a plate: slow-baked chickpeas, rabbit or pork stifado, wild capers and their leaves, the local white aubergine, tomatokeftedes made with the small Santorini tomato. The bill is a fraction of Oia and the cooking is the reason you came.

The move  Go inland to Exo Gonia or Pyrgos for lunch, take the table with the most Greek families and no menu in six languages, and ask what came out of the oven that morning.

Map  Exo Gonia

07

Wine

Assyrtiko beyond the obvious, the estates worth the drive

Everyone is bussed to the one big winery on the coach circuit. The Assyrtiko worth the day is inland, in the vine country around Pyrgos, Megalochori and Exo Gonia, where the older estates pour in the shade of their own cellars. The names to plan a tasting around are Domaine Sigalas up at Oia's edge, Estate Argyros near Episkopi, Gaia on the Kamari road and Artemis Karamolegos at Exo Gonia, each pouring bone-dry Assyrtiko, aged nykteri and sweet Vinsanto from vines grown on volcanic ground with no rain. Two estates in an afternoon is plenty, and a driver turns it from a logistics problem into the best half-day on the island.

The move  Book two tastings in advance, an hour apart, and let a driver carry you between them. Ask each estate to pour their nykteri, the barrel-aged Assyrtiko, next to the young one, so you taste what the island does with age.

Map  Santorini wine country

08

Eat

Tomatokeftedes, fava and white aubergine, ordered right

Three things grow well on volcanic rock with almost no water, and Santorini has built its table on them. Tomatokeftedes are fritters of the tiny, intense Santorini tomato bound with herbs and fried, best eaten the moment they land. Fava is not the broad bean of the mainland but a purée of yellow split peas grown on the island, served warm with raw onion, capers and good oil, and the version topped with slow-braised onions, fava me katsoula, is the one to look for. The white aubergine is sweeter and less bitter than the purple, fine simply grilled or fried. Order all three as a start and you have the island in miniature before the mains arrive.

The move  Start any island meal with fava, tomatokeftedes and white aubergine to share, and ask whether the tomatoes and the fava are Santorini-grown, because the PDO ones are the point.

Map  Pyrgos tavernas

09

Drink

A late glass at Merlin, off the caldera rail in Fira

Fira after dark is mostly the loud strip, but a proper late drink is still there for anyone who steps off the caldera rail. Merlin is the one to know, a cocktail bar set back a little from the cliff-edge crush, where the drinks are made with care and the room is for drinking rather than queuing for a photograph. Come after dinner, once the day-trippers have gone back down to their ships and the village empties, and take a slow glass over the last of the caldera light. It is the civilised end to a Fira evening, a real bar rather than a view with a mark-up.

The move  Go late, after the dinner rush and the last cruise tender, ask what the bar makes with Greek spirits, and take the glass slowly rather than chasing the strip.

Map  Merlin, Fira

10

See

Pyrgos, the village to climb when Oia is full

When Oia is a queue, drive up to Pyrgos instead. It is the old capital, the highest of the inland villages, a knot of white lanes and stairways climbing to a Venetian castle at the top, and from that rim you get the whole island laid out and the caldera in the distance without a single tour group in the frame. The walk up through the medieval kastro takes twenty unhurried minutes, past small churches and courtyards where people actually live. At the top there is a café or two for a coffee with the view, and at sunset the light here is as good as the coast, minus the crowd. It is the quiet answer to the famous village.

The move  Come to Pyrgos in the late afternoon, climb the lanes to the castle at the top, and take the sunset from the rim with a coffee, then have dinner in the village below.

Map  Pyrgos

11

Walk

The caldera walk, and the direction to walk it

The best walk on Santorini runs along the caldera rim from Fira to Oia, roughly ten kilometres of paved lane, cobble and dirt path through Firostefani and Imerovigli, with the drop and the blue sea on your left the whole way. Walk it north, Fira to Oia, not the other way, so the caldera stays on your left and you are heading toward the sunset rather than away from it. Allow three to four hours with stops and go early or late, never in the noon heat, because there is little shade on the open stretches past Imerovigli. Above Imerovigli, at the forks, take the left-hand paths for the caldera views rather than the easier inland route. End it in Oia and take a taxi or the bus back.

The move  Start in Fira by late afternoon, keep the caldera on your left all the way to Oia, carry water and a hat, and arrange your ride back before you set off, since taxis out of Oia are scarce.

Map  Fira to Oia path

12

See

The Pompeii of the Aegean, at Akrotiri

In the south of the island, under a great modern roof, Akrotiri is a Bronze Age town buried whole by the same eruption that shaped the caldera, its streets, drains and three-storey houses preserved in ash like a mini-Pompeii, some four thousand years old. You walk raised gangways above the excavation and look down into rooms where the great frescoes once stood, before they were lifted for safekeeping. It is cool, shaded and out of the sun, which makes it the right thing to do in the heat of the day when the caldera villages are unbearable. Give it an hour, then pair it with the frescoes themselves in the Fira museum.

The move  Do Akrotiri in the middle of a hot day, when it is shaded and the villages are not, then see the lifted frescoes at the Museum of Prehistoric Thera in Fira to complete the picture. Check the day's hours, they are shorter on one weekday.

Map  Akrotiri site

13

Beach

Red, White and the lunar beach in the south

Santorini's beaches are not sand and turquoise, they are volcanic, dark and strange, and that is the reason to go. The Red Beach near Akrotiri sits under a wall of rust-red cliff, dramatic to look at, though rockfall means the access is sometimes restricted, so check before you scramble in and view it from the headland if the path is shut. The nearby White Beach, reached by a short water taxi from Akrotiri, sits under pale cliffs and is quieter. For a true lunar stretch, the black volcanic sand of Perissa and Perivolos on the south coast runs for kilometres, with organised beach bars and clear water, and it is where islanders actually swim. This is beach as landscape, not as postcard.

The move  See the Red Beach from the headland and check whether the path is open before climbing down, take the water taxi to the White Beach for the quiet, and swim off the black sand at Perissa or Perivolos.

Map  Red Beach

14

Drink

The donkey beers, the island's craft brewery

Wine is the island's headline, but there is good beer too. The Santorini Brewing Company, started by four brewers in 2011 as the island's first brewery, sits in Mesa Gonia on the road between Fira and Kamari, and its Donkey range has become the local drink of choice: the Yellow Donkey pale wheat ale, the Crazy Donkey IPA, the Red Donkey Irish red, and a White Donkey wheat beer, with the rare Slow Donkey barley wine aged for over a year. It is small, unfussy and open for tastings by day, a proper working brewery rather than a show. It makes a fine, cheap break from the wine trail and a case is easy to carry home.

The move  Drop in during the day for a tasting flight of the Donkeys, try the Crazy Donkey if you like it hoppy or the Yellow if you don't, and check the current opening times before the drive.

Map  Santorini Brewing Company

15

Know

Why the vines grow in baskets on the ground

Look at a Santorini vineyard and you will not see rows on wires. The vines are trained into low coiled baskets on the ground, the kouloura, woven over decades so the grapes grow inside the ring, sheltered from the fierce wind and the salt, and cooled by dew and mist because it almost never rains here. The volcanic soil carries no phylloxera, so some of these vines are astonishingly old, and the whole system is a piece of living heritage as much as farming. Knowing this changes how the wine tastes: the mineral, salt-edged bite of a good Assyrtiko is the ground and the wind in the glass. Ask at any estate and someone will happily show you a basket up close.

The move  Ask at a tasting to walk into the vines and see a kouloura basket, and taste the Assyrtiko knowing the salt and mineral come straight from that volcanic ground.

Map  Santorini vineyards

16

See

Sunset from the monastery, not the mob

The highest point on Santorini is Profitis Ilias, 567 metres up between Pyrgos and Kamari, crowned by a monastery founded in 1712. From the terrace beside it the whole island falls away, the caldera on one side and the open Aegean on the other, and at day's end the light does everything the Oia crowd is fighting for, with almost no one beside you. The road up is a proper climb best done with a car or driver, and the monastery keeps its own hours, so it is the setting rather than the interior you come for. Take the sunset here and you trade the scrum on the cliff for a quiet rim and the best single view on the island.

The move  Drive up to Profitis Ilias for the hour before sunset, take the view from the terrace by the monastery, and come down into Pyrgos for dinner afterwards rather than fighting the Oia traffic.

Map  Profitis Ilias

17

Eat

Dinner down at the water in Ammoudi

Below Oia, a steep flight of some three hundred steps drops to Ammoudi, the little red-rock fishing harbour where a handful of tavernas set their tables right at the water's edge. This is where you eat the day's catch, grilled whole fish and octopus hung to dry in the sun, with the boats rocking beside you and the cliff going pink overhead as the sun drops. It is more expensive than an inland taverna and it trades partly on the setting, but the fish is fresh and the position is genuinely lovely once the sunset crowd up top has thinned. Walk the steps down, or take a car round by road if your knees prefer.

The move  Book a waterside table for after sunset, once the crowd on the Oia steps has cleared, order the fish by the kilo and agree the price first, and arrange a car back up rather than climbing the steps after dinner.

Map  Ammoudi Bay

18

Walk

Megalochori and Emporio, the villages nobody photographs

Two inland villages give you the old Santorini without a caldera crowd. Megalochori is a small maze of white lanes, bell towers and captains' mansions around a quiet square, a few minutes from the wineries and lovely to wander in the early evening. Emporio, the largest of the traditional villages, hides a medieval kastro, a warren of vaulted lanes and windmills on the hill above, where you can walk for an hour and meet more cats than people. Neither is on the postcard, which is exactly the point: they are where island life carries on, with real tavernas and no one selling you a boat trip. Half an hour in each, a coffee, and you have seen the Santorini that the cliff hides.

The move  Wander Megalochori's square in the early evening and lose yourself in Emporio's kastro lanes and windmills, and pair either with a nearby winery on the same afternoon.

Map  Emporio

19

Eat

The gyros the island actually queues for

Not every meal here is fine dining and a caldera view. For the cheapest good lunch on the island, join the line for a gyros or a souvlaki at a proper grill in Fira or one of the working villages, where locals and hungry workers queue for pork or chicken wrapped in a warm pita with tomato, onion and chips for a few euros. It is fast, filling and honest, the antidote to a week of thirty-euro mains on the rail, and the queue of Greeks rather than tourists is how you tell the good one. Eat it standing or on a step, cash in hand, and save the sit-down money for the wine.

The move  Find the grill in Fira with the longest line of locals at lunch, order a pork gyros to go, and carry small cash, since these places rarely take cards.

Map  Fira for gyros

20

Buy

Vinsanto, the sweet wine to carry home

The one bottle to take off the island is Vinsanto, the amber sweet wine Santorini has made for centuries from Assyrtiko and Aidani grapes sun-dried on straw mats until they raisin, then aged for years in barrel until it turns deep and honeyed with a lick of the island's acidity to keep it from cloying. It is the wine the monasteries once sent across the sea, and a good aged one, ten or twenty years in wood, is a serious thing to open at home with dessert or hard cheese. Every proper estate makes one and will let you taste it at the end of a flight. Buy it at the winery, not the airport, and let them wrap it for the case.

The move  Taste the Vinsanto last at any tasting, ask how many years it spent in barrel, and buy the older one at the estate rather than the airport, wrapped for the flight home.

Map  Vinsanto estates

21

Know

Ferry, port and the airport, without the panic

Two ways on and off the island, and both reward planning. The ferries dock at Athinios, a working port with no town, a steep zigzag road up, and a scrum of taxis, buses and hotel cars all arriving at once when a big ship lands, so book your transfer ahead and know your driver's name. The fast catamarans are quick but cancel first in a strong meltemi wind, so build a buffer day before an onward flight and do not book the last ferry that connects to your plane home. The airport is small and jams badly at peak, so arrive early. Bring a printed or offline ticket, because the queues eat your time and the signal is patchy.

The move  Pre-book your port and airport transfer, leave a buffer day before any onward flight in case the ferries cancel for wind, and get to the small airport well ahead of a peak-season departure.

Map  Santorini Airport

22

Do

The boat to the volcano and the hot springs, done right

The caldera is a drowned volcano, and the boat trip out to the two black islets at its centre, Nea Kameni and Palea Kameni, is the one excursion worth the ticket. On Nea Kameni you walk up a bare crater still venting sulphur, the raw geology that made everything you have been photographing. Off Palea Kameni you swim from the boat into a warm, rust-coloured bay fed by iron-rich hot springs, cooler than the name promises but a strange, memorable dip. The trap is the giant sunset party boats, packed and rushed. Take a small or morning boat instead, when the crater is not an oven and the springs are not a crowd, and wear a dark swimsuit the iron will stain.

The move  Book a small-group or morning boat rather than the big sunset cruise, wear an old dark swimsuit for the iron springs and shoes you can climb the crater in, and carry water for the shadeless walk up the volcano.

Map  Nea Kameni volcano

23

See

The renovated museum in Fira worth an hour

The Museum of Prehistoric Thera, in the centre of Fira, is where the treasures dug out of Akrotiri actually live, and it is the one indoor hour to give the town. Its rooms hold the great wall-paintings lifted from the buried city, since redisplayed on the upper floor the way they once stood in the houses, alongside gold, painted pottery and the everyday objects of a Bronze Age town four thousand years old. It is small, cool and never as mobbed as the sites outside, so it slots neatly into the hot middle of the day. See it after Akrotiri and the ruined town and the frescoes finally join up into one story.

The move  Pair the Museum of Prehistoric Thera in Fira with a visit to the Akrotiri site, ideally the same day, go for the upper-floor frescoes first, and use it as a cool hour in the heat. Note the Archaeological Museum nearby is a different, smaller collection.

Map  Museum of Prehistoric Thera

24

Eat

Breakfast like a resident, not a guest

Skip the hotel buffet for one morning and eat the way the island does. A village bakery, a fournos, will sell you a warm cheese pie, a koulouri, or a bougatsa fresh from the oven for a couple of euros, best eaten on a step with a coffee from the kafeneio next door. In the inland villages, Pyrgos, Megalochori, Emporio, the morning is slow and quiet, the tourists still asleep up on the rail, and you get the real rhythm of the place with your coffee. For something sweeter, look for melitinia, the little Santorini cheese-and-honey pastries, in the bakeries around Easter and through the summer. It costs almost nothing and it is the most local hour of your day.

The move  Have one breakfast at a village fournos rather than the hotel, order a cheese pie and a Greek coffee, and take it slowly in an inland square before the day heats up.

Map  Megalochori village

25

Know

Cable car, mules and donkeys, and what to do instead

Between Fira and the old port below there are three ways up and down the cliff, and two of them are traps. The cable car is quick and cheap but jams to an hour-long queue whenever a cruise ship empties, so use it only off-peak. The mules and donkeys that carry tourists up the stepped path are the thing to skip outright, on welfare grounds, the animals are worked hard in the heat and the practice is widely and rightly criticised. Walking the zigzag steps down is doable but they are steep, slick and fouled by the animals. The honest answer is to arrive by ferry at Athinios instead of tendering to the old port, and to ride the cable car only when there is no ship in.

The move  Take the cable car only when no cruise ship is in, never ride the donkeys, and if you are coming by sea, land at Athinios port rather than tendering to the old port under Fira.

Map  Fira cable car