Sailing solo in Santorini

On an island seemingly made for couples, what remains for the lone traveller?

It is plain to see why Santorini is a hotspot for destination weddings and amorous getaways. Despite the island’s popularity, it’s not difficult to find a secluded spot to take in the spectacular views with the love your life – the cobalt blue Aegean waters and outrageously stunning sunsets can inspire romance in even the hardest of hearts.

With every corner you turn there’s yet another love-struck couple taking lip-locked selfies, or perched at a bar counter in a quaint alleyway, or lounging together beside a pool overlooking the caldera. Surely Santorini must be a lonely and unbearable place for the single, solo, and perhaps cynical traveller? What enjoyment could there possibly be for a solitary Australian backpacker?

Plenty, it turns out. On a five-month trip through Europe and the Middle East last year, the winds eventually brought me to Santorini in late September. After a week in Athens speaking to locals and fellow sightseers, the unanimous opinion appeared to be that, as lovely as the other Aegean and Ionian islands are, Santorini was unmissable.

A few days later I found myself standing on the deck of a ferry, sleep-deprived from a late night out in the Psirri district, staring at Santorini in the distance. In my drowsy haze I was surprised to see what I daftly thought were dustings of snow at the peaks of the caldera. I soon realised that these apparent snow caps were actually the whitewashed buildings of the scenic northern town of Oia, where I was to spend the next few nights in the local hostel.

Unfortunately, the summer of 2014 was to be Youth Hostel Oia’s final season in business – which is a severe shame as it was an outstandingly picturesque and tranquil hostel, and budget accommodation in Oia is a rarity. Hostels are, of course, wonderful hubs for meeting fellow lone explorers seeking a day trip companion or drinking sidekick, and there are still a handful scattered throughout Santorini.

Oia itself is the classic image that comes to mind when someone mentions Santorini; a jumble of white walls, blue domes, and a maze of pathways, situated daringly close to the edge of the cliffs that drop sharply into the water. It also happens to be one of the most popular spots in Santorini to watch the sunset, and the foot traffic moves at a snail’s pace throughout the town’s narrow paths during the early evening, particularly around the prime viewpoints on Oia’s western edge.

However, the joy of staying locally was to be able to buy a snack and a can of beer, and then claim a good spot to view the sunset (ideally, the Byzantine castle ruins) before the tour buses from other parts of Santorini arrived. To sit in the same spot for about two hours might sound incredibly dreary to some, but with such a marvellous view and the occasional stranger to talk to, I found it to be a completely effortless pleasure.

For the solo traveller wishing to escape the maddening crowds – or, alternatively, for those who feel pangs of guilt for spending their days lounging about – a hike between Oia to Fira, the island’s main town, is the perfect remedy. Only a moderate level of fitness is required for the 10 kilometre path, and depending on your pace and adventurousness, will take anywhere from two to four hours.

The views on this hiking route are, quite simply, unmatched by anything else on Santorini. The path follows close to the ridgeline for much of the way, and takes you through small villages, past some isolated churches, and will also give you a glimpse at some of Santorini’s most exclusive, secluded, and eye-wateringly pricey resorts.

Whilst passing through the village of Imerovigli it’s worth taking an extra hour to detour into Skaros, a rocky peninsula featuring the ruins of a medieval Venetian fortress built in the early 1200s. Skaros was the former capital of Santorini, and the steep cliffs and narrow access from the main island ensured it would be impenetrable to attack. Conversely, it also made life extremely inconvenient for its inhabitants. After a series of eruptions and earthquakes it was left virtually abandoned by the 1800s. Little remains of the buildings, but Skaros is uniquely positioned to provide a clear view of both Oia and Fira.

Upon reaching the end of the hike, it’s not a bad idea to find a bar overlooking the caldera and order a hard-earned wine or beer. In fact, it seems that a lot of relaxation in Santorini involves a drink or two, and for those so inclined, one of the finest places to indulge in a drop is Santo Winery, just south of Fira. This is where fellow hostel dwellers and your powers of persuasion may be required; after all, good drinks are best enjoyed in good company, and drinking alone amongst tables of honeymooners and families is a fast track to feeling the pinch of loneliness.

As always, despite the sprawling terrace, it’s best to arrive well before sunset to snag a well-positioned table. I decided upon a tasting platter of 12 wines; the price also included a generous portion of croutons and cheese, but following such ample servings of Santo Winery’s finest I’m admittedly at a loss to recall the exact price. However, I certainly remember it being modest, and the wines very agreeable to the palate. Despite Oia’s reputation as being the must-visit locale for sunsets, on this particular day the heavens and the earth conspired to conjure up the most memorable sunset I’ve ever witnessed. Santorini’s reputation for this phenomenon is certainly warranted.

Getting around the island isn’t terribly difficult, but for a true sense of freedom it’s hard to beat a scooter or quad bike, either of which can be easily rented. My quad bike adventures took me across the full length of the island, and within an hour I was having lunch on the southern edge of Santorini in the town of Perissa, known for its black sand beaches and more relaxed, alternative atmosphere. Following a visit to the magnificently preserved Minoan ruins of Akrotiri, dating back well over 4,000 years, my sense of adventure took hold and I decided to ride up to the highest point in the island. Aside from housing a military radar facility, it’s also the location of the Profitis Ilias monastery and chapel of St Nectarios. Whilst neither offer terribly much to see, it is, unsurprisingly, the view from the mountain that is the main drawcard.

For such a relatively small island there is absolutely no shortage of cultural, culinary and outdoor pursuits to be experienced by the intrepid solo traveller in Santorini – so much so that my intended three-night stay turned into eight nights, and there are yet more activities I didn’t get around to trying. So who knows, perhaps one day in the future I’ll be able to return to Santorini to indulge a little further – and just maybe, I’ll be on holiday with my spouse, cosied up in the corner of a bar, making a younger solo traveller roll their eyes as they pass by.

* Ashley Loh-Smith is a frequent traveller and freelance writer.