A First-timer’s Guide to Santorini

Santorini is the Greek isle in your imagination. Here, every glimpse is a postcard: pristine white buildings gather on a rocky cliff faces like crooked teeth and bulbous blue domes of churches perfectly match the colour of the Aegean.

During summer, this tiny island in the scatter of the Cyclades is often so overrun with slow-strolling tourists it seems it might sink; for a place of around 16,000 residents, the two million annual visitors (mostly during July and August) make their presence known. But despite the hordes, Santorini remains a place of true, unrivalled beauty – and that’s why the crowds return, year after year. Here’s how to have a memorable trip.

The run-down

The main towns of Fira, Oia and Imerovigli receive the majority of the summer crowds due to their west-facing locations, with Oia experiencing an additional spike in the hours before sunset – its location on the island’s northern curl, makes it a perfect lookout. July and August are peak times but the island still offers warm weather and sunshine from May to October (average temps sit around 22C) so reconsider your timing if you want more of the island to yourself.

If you’ve booked for peak time, don’t fret – Santorini’s sights still manage to override any crowds. Plan to do the bulk of your exploring in the early mornings and try and visit inland towns such as Pyrgos (see below) during the day to avoid the crowds.

There’s a small airport on the island but if you can, catch a ferry from Athens, usually around five hours – the bus ride snaking up from the ferry terminal is stunning. Once you’re there, cities are easily traversed on foot and while travelling between main towns is possible by bus (with its questionable timetables), a rental car is the most reliable option.

Do

Walk the Fira to Oia trail

It’s unlikely you’ve come to a Greek isle to hike but the track between the island’s two main towns, Fira to Oia, is worth pulling on proper shoes for. The 10-kilometre stretch runs through the quieter towns of Imerovigli and Firostefani, as well as skimming the island’s eastern edge, overlooking the caldera; if you came to Santorini for views, this is unmissable.

Visit inland towns

Authentic experiences here are rare but not impossible; a turn around the inland town of Pyrgos, where the population barely tips over 1000 residents, is a welcome change from Oia’s oft-choked avenues. It’s also sat on the highest point on the island, rewarding visitors with yet more panoramic views.

Sip a local drop

The island’s wine production is also of note, thanks to volcanic terroir where rare varietals such as assyrtico, aidini and athiri – all indigenous to the island – flourish. Sample some of the best results at Domaine Sigalas, a winery 10 minutes east of Oia or Santo Winery in charming Pyrgos.

Watch the sunset – without the crowds

Watching the sunset over the caldera is a must – and it doesn’t have to resemble a stage-front crowd at a festival. While the walkways around Oia Castle are a veritable ant’s nest, snagging a table at vantage spots such as Argo or PK Cocktail Bar instead will ensure you can admire the view with plenty of space. Just be sure to secure a place well in advance (and often, be willing to pay a pretty penny for the experience).

Although Oia arguably offers the best angle to see both the inimitable sundown throw its colours all over the town and the caldera, booking a table at Santo Winery is a worthy alternative. From one of the highest points on the island, you can farewell the day with a glass in hand, the entire island splayed out in front of you.

Swim somewhere other than a hotel pool

Because of Santorini’s elevated position, beaches aren’t the island’s main drawcard. The east is the “beach side” but sands are volcanic (black or red, and named as such), not particularly picturesque and relatively hard to reach unless you have a car or order a taxi. Consider setting up a towel at Amoudi Bay near Oia (there’s limited space so get there early) or at Vlychada in the south, where the surrounding cliffs provide a spectacular scene. In either case, a hire car is the best bet for a beach day.

Stay

Make an yposkafa – the traditional cave-like buildings of compacted local materials of lava, ash, sand and pumice stone – your temporary home, if you can. Properties such as Fira’s Perivolas and Santos Maris Oia Luxury Suites and Spa are expertly spartan and sleek, giving the ever-present caldera it’s rightful place in the spotlight. In Imerovigli, Kapari Natural Lodge is an atmospheric choice, with its shell dating back some 300 years.

Eat & drink

The humble pita gyros is ubiquitous and necessary anywhere in Greece; your top choice in Santorini is Pitagyros Grill House in Oia, which does what is says on the tin (and very well). The traditional tavern Aktaion in Firostefani serves very delicious Santorinian specialities such as octopus with fava and sweet capers for very affordable prices and Pyrgos’ Agaze is a bright, laid-back choice for hearty breakfasts.

The island’s best bar are those that have made the view as important as their menus. Fira’s Tango Cocktail Bar is one such place, with a terrace that hangs off the cliffside, the caldera almost within reach.

Skirted chairs aside, The Wine Bar atop the Heliotopos Hotel in Imerovigli is another great option with stunning views over the island’s western edge.