If you are going to hop the Greek Islands, is there any better way of doing it than by custom cruise? No, darling, there is not.

An emotion I could not immediately name hit me when I woke
up to see that we’d sailed to Santorini.

Looking out at its callous beauty – the water a gas flame-blue, the cliff tops brandishing a chaos of sugar-cube houses – it wasn’t so much a déjà vu or, well, even a déjà cruise (given that I’d arrived there in the middle of a summer night, courtesy of Silversea). It was closer to a certain wistfulness goosed by … yes … nostalgia.

Planting my feet, soon enough – on this, an island that owes its beauty to a venomous volcano, circa 1600 BC – it was a feeling that would only grow: nostalgia, a word stemming, as it happens, from the Greek, nostos (homecoming) and algos (pain).

How fitting.

Strange, though – especially considering that while I’d been to Greece before, Santorini, in particular, had, until now, eluded me. But, then, it hit me: Instagram! In a time when it’s one of the fastest growing social media gateways – one that’s a big moving billboard and a map of the world we cart around in our hands – I had, indeed, been to Santorini without visiting Santorini.

Paging Alice. It’s Through the Looking Glass!

With this pic-perfect island easily being one of the places showing up with regularity on Instagram – a feed where an average of 95 million photos are shared a day – the whole idea of not knowing (the thrill of travel for so long) has become somewhat elemental. Like clockwork, every summer, for the last several years, they’ve come, after all: images from the Aegean Sea galore, particularly from Greece-loving celebs ranging from Rihanna to Hugh Jackman to Katy Perry.

The upshot, wanderlust-wise? Not only one of the biggest disruptions to happen in the tourism racket at large – “Now you’re less than 10 clicks away from seeing an image on Instagram to purchasing a ticket to go there,” as travel photog Chris Burkard once put it to National Geographic – but, possibly even more intriguing, a more existential shift to the way we “experience” places and things.

A view of a cliffside town in Santorini featuring multiple spherical roofs and multicoloured structures.
Oia, one of Santorini’s cliffside towns. (Photo: Allard Schager/Getty Images)

Bingo: the feeling of longing and even melancholy I felt bubbling up when I landed in Santorini. I had a familiarity with the familiar!

Having said all this: if you are going to hop the Greek Islands, is there any better way of doing it than by custom cruise? No, darling, there is not. For, what is cruising – to stay with the theme of screens – if not scrolling by sea?

Starting and ending in Athens on this particular odyssey in an Italian ship christened Silver Spirit, it was validation of what I’ve known for a while as a Silversea vet: a stately non-densely populated vessel on which all guests get their own on-call butler (should one need to ring for fresh limes, for instance), and most suites coming with its own veranda (all the better for spending hours looking out idiotically at the sea and/or watching islands recede in the distance when the ship departs).

Immunized from the well-known horrors of air travel 2018-style and free from the packing-unpacking – “Sir, laptop in the bin … Ma’am, shoes off” – prospect of globetrotting as you go from place to place, the merits of cruising on a high-end ship really cannot be overstated.

Did I also mention that you don’t take out your wallet the entire time that you’re on board? Well, yeah, I just did. (Everything but everything is included). Or that there are myriad elegant restaurants to choose from and “room service” doesn’t only extend to the literal (you can have food delivered to any public area of the ship, whether it’s to the Panorama Lounge, the Observation Library or even the quite good jazz lounge). Well, consider it said.

In terms of a crash course in Greece, we were good students. In Mykonos, we meandered through the Old Town, where a slew of white-washed buildings and beckoning high-end boutiques take you down maze-like alleys on which widows in black can be seen hanging their washing and where, at one point, my travel companion and I even found ourselves following a human-sized pelican we encountered on our way to visit the island’s signature white windmills. In Patmos, meanwhile – a more in-the-know island – we made the hillside climb to the Monastery of Saint-John the Theologian and the Cave of the Apocalypse, where St. John is said to have received the Revelation in AD 95 and later found further religion in fresh-caught fish while imbibing on a beach renowned for its glittering multi-coloured pebbles.

One of the best parts of our nautical adventure? When the Silver Spirit veered off course for a smidge, landing in a Turkish port, where one of the add-on excursions included a chance to go see a sunset-timed classical concert set at the Temple of Artemis. Unfolding among the columns in a “ruined” open theatre, it was an evening to soak in all right. (And one of the extras that the cruise line is famous for on its voyages around the world – ranging from hot-air balloons above the Namibian desert to gorilla spotting in the Uganda.)

Sitting in the bygone temple on this particular night, as the sky darkened above us and the music played on, it was one of those oh-so-fleeting moments: a juncture when a gap still remains between our expectations and our travelling reality.

Nostalgia, play thy game.