As I watched the sun descend in a haze of vanilla and scarlet over one of the world’s most famous volcanic calderas it was easy to understand why ‘Santorini honeymoon’ was one of the most popular Google searches in 2024. Far beneath me, the volcanic crater plunged in layers of red and black lava to the wine-dark sea beneath, whilst Oia’s whitewashed cave hotels perched on the crater’s rim above me like icing on a wedding cake. In summer, Santorini’s famous sunset spot near the ruins of its Venetian castle would have been packed with punters battling to get their selfies. In February, however, there were only half a dozen of us admiring that spectacular view. “My friends will think I’ve used Photoshop when they see my pictures of Santorini with hardly any people,” I heard someone say.
Like its overtouristy peers Barcelona and Venice, this 76km squared Cyclades island, which attracts 3.4 million visitors per year has had a lot of bad press recently. “We face all the problems of a big city, even though we are not designed to be a big city or to deal with these problems,” mayor Nikos Zorzos told reporters in 2023. Much of the blame for overcrowding is put on cruise ship tourists – there can be as many as 17,000 per day. In a bid to combat the problem, Greece’s tourism minister Vassilis Kikilias launched a programme to encourage tourism out of season. And in 2024, a handful of hotels and restaurants began opening their doors in winter. “People who come here between December and March want to discover the real Santorini – the one most people never see,” Nikos Boutsinis of Santorini Walking Tours told me later as he led me on a hike along the cobbled caldera footpath that leads from Fira to Oia.
Most of the glitzy caldera-edge hotels remain closed out of season, however, so I was staying at Santorini Sky, a sleek villa complex on the slopes of Profitis Ilias the island’s highest mountain. “Santorini is the quintessential romantic experience so we’re always open on Valentine’s Day – we have the hottest Jacuzzis on the island and plenty of treats for our guests,” enthused owner Daniel Kerzner as he showed me to my sky-high villa. “The big advantage at this time of the year is that there are far fewer crowds of course, but it also generally stays warm and accommodation is more affordable,” he added.
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Stripped down to shorts and T-shirt, the following day I breakfasted on sugar-dusted slabs of custard-pie bougatsa by my pool, glittering like molten lead in the 20C heat, before heading out to visit Fira. When I’d visited the island’s capital a few months earlier, it was a football scrum packed with cruise ship passengers. In February, however, there were only five of us oohing and aahing at scenic views over the crater’s volcanic core as the funicular whizzed us down to Skala Port, and back up again. “We love it here at this time of the year – we have the archaeological sites to ourselves and we’ve found some great tavernas where only the locals go,” an elderly couple from Houston confided.
In the centre of Fira, most of the souvenir shops were closed, but I found a store selling local treats: linen bags of yellow split pea fava, sun-dried sugar-sweet cherry tomatoes, raisin and sesame seed rolls kopania, and carafes of punch-packing white spirit tsipouro. After spending an absorbing hour in the Museum of Prehistoric Thera where finds from Akrotiri, the Minoan site known as “the Greek Pompeii”, are showcased, it was time for lunch. On Daniel’s suggestion, I chose Pelican Kipos, a family-run taverna overlooking a flower-filled courtyard near Fira’s bus station where they serve hearty home-cooked food ranging from crispy marathopita fennel pies to xoirino krasato – pork fillet slow-cooked in a syrupy Vinsanto wine sauce. Down in the restaurant’s four-centuries-old wine cellar afterwards, I sipped golden Assyrtiko and other local wines by candlelight with sommelier Maria, who told me that most of the island’s wineries stay open in winter. “The people who work in them are more relaxed at this time of the year, so you can chat and learn a lot more,” she told me as the candle’s light cast crazy shadows over the wine cellar’s low domed walls.
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Santorini might be best known for its caldera-side resorts, but the island also has a string of picturesque villages further inland. Surrounded by a ruffled sea of vines, Pyrgos is a flower-studded jumble of steep lanes lined with hole-in-the-wall tavernas, quirky art galleries and terrace bars clustered around the crumbled remains of a 16th-century castle, whilst Emporio’s narrow lanes lead to countless ancient edifices, including Palia Panagia which is one of the island’s oldest churches. I ended my own tour in mediaeval Megalochori where wild-haired, white-bearded ceramicist Andreas Makaris taught me to throw pots in his grotto-like shop. Splattered with dobs of clay, we sipped thimbles of white spirit raki served up with Andreas’ wife’s buttery, nut-filled kourabiedes biscuits. “Out of season is when our island shows its real face,” Andreas said raising his glass in a toast. “If you’re really looking for romance, winter is the time to visit Santorini.”
Read more: The lesser-known romantic city breaks for Valentine’s Day getaways, away from the crowds
How to get there
Although it’s a three-day trip it’s possible to take the slow route to Santorini, starting with a romantic ride on the Orient Express from London to Venice, followed by a 26-hour “cruise” aboard the Venice to Igoumenitsa ferry, and then a complicated series of bus rides to Piraeus, where ferries leave for the five-hour journey across sparkling seas to Santorini.
Alternatively, Aegean Airlines have flights from London Heathrow to Santorini via Athens, from £147.
Where to stay
Apart from Santorini Sky near Pyrgos, there are a handful of hotels that stay open in the winter months. If you’re seeking a cool budget option check out Helianthus Suites or Angel Cave Houses.
What to do for romance
Down a raki with Andreas at Earth and Water Studio, and then make a beeline for Akrotiri, the impressive Minoan site that was buried under lava and ash after the volcanic eruption in 1600BC. Santorini Yachts organises chartered catamaran trips across the caldera, with a stop-off to splash around in hot volcanic springs. Afterwards, catch the best sunset views at Naoussa in Fira or enjoy some of the best no-frills food on the island at rustic seafront taverna Lava near Perissa.
Read more: Budget-friendly and blissfully crowd-free – why you need to head for the Greek ski slopes this winter
Source: independent.co.uk