I admit, when I left Europe and moved to North America, I didn’t think I’d be going on vacation in Europe again for quite some time. I thought that after nearly 8-months of driving around Europe in a van, and having visited just about every country (yet to visit San Marino, Serbia, Macedonia, and Kosovo), I would have little reason to return.

However, due to the ambitious schedule, time and cost of the motorhome trip, there were just a few places that were skipped – and one of those places happened to be the Greek Islands (which is a pretty generic description for a very large and diverse area).

As luck would have it, I was invited to join a Greek friend that was returning for their summer vacation. It was a long way to travel, but the offer to travel to some unique areas with someone that had intimate knowledge of the area was too hard to turn down.

So, after nearly 24hrs of travel, including a flight from San Francisco to Istanbul, another flight from Istanbul to Athens, and a final short hop from Athens, I was finally in the Cyclades. It was nearly midnight, and with a combination of excitement and (mostly) jetlag, I was excited to go explore Santorini. Jetlag and the need for a warm shower won. We did go for a quick walk to a small nearby cove, and even in the narrowly focused illumination of a head torch, I was excited for what lay ahead in the daylight.

Day 1 – Thirasia

The fatigue hit as soon as I had showered and made it to bed. It felt like no time had passed, yet it was already morning, and the sun was starting to make its way over the peak of the hills above us and lighting up the bay. We figured there was no better way of combatting jetlag than going for a quick swim, so we returned back to the small cove, and swam across to the small island with its church of St. Nicholas. I wore a pair of goggles, and the clarity of the water meant I was able to see just how deep the water was, which had me struggling to breathe with something almost resembling fear – though, I won’t admit it was fear, because it’s irrational to be afraid of swimming over a unfathomably deep body of water, with sides that seemed to just plunge vertically into an abyss… Plus, the myriad of ropes that snuck across the bay like vines made it seem even more otherworldly. I held my nerve, calmed my breathing, and climbed up to the church, before promptly jumping back off the ledge into waters that so recently had me in a state of semi-panic.

A quick breakfast of yoghurt, fruit and a bread roll were accompanied by a cappuccino – though, their and my interpretation of a cappuccino were at odds. It was a small glass of Greek coffee, topped with load of whipped cream from a can, dusted with cinnamon/nutmeg. At the end of the day, it was still coffee – though at nearly €30, I’d probably get better value in San Francisco!

Shortly after breakfast, my friend’s friends came to collect us in a small boat for an adventure across the bay on the smaller island of Thirasia. I was in awe from the moment I stepped onto their boat, until the moment I stepped off, long after sunset. I’d been in the country less than 12hrs, and already I was being whisked away to relax at a luxury private villa, the kind of place regular people don’t know exist, let alone have the ability to book or visit. Here was a place that was built into the sides of the cliffs, made from the same rock that was previously quarried here, blending in spectacularly, yet finished with great luxury.

We made our way up to the infinity pool that had been carefully built into contours of the hillside, and after a thorough coating of some new black-magic sunscreen (I, a pasty ginger skinned white guy, didn’t get remotely burnt once in nearly three weeks of Mediterranean sunshine, and can only attribute this to magic), I was floating in the pool, amazed at the views I was enjoying. It was stupendous, and I was already recognising that I’d made the right decision to come on this holiday – and it was only Day 1.

After an hour-or-so of alternating between sunbaking and floating around (who’s keeping track of time), we decided to be a little more adventurous, and took some stand-up paddleboards for a quick paddle. The waves were minor, but enough to give me concern, and I stuck to kneeling. It was warmer than San Francisco, but it was still chilly enough to make me not want to get wet if I didn’t need to.

I wasn’t confident enough to make a long journey on these boards, so they were swapped out for sea kayaks, from an absolute treasure trove of water toys in their boatshed. From our friend’s villa, we paddled out and around a small cape, and to a nearby beach. I’ve always fancied the idea of doing a long sea kayak journey, and this was my first taste of that – even though in reality it was likely less than 2km and 30mins each way. The waves were gathering strength, and in places it had the smaller of the two kayaks rocking quite violently.

Still, there was something truly exhilarating about being so exposed, and being surrounded by amazing views in all directions.

Birds eye view of the caldera, with Thira in the background, and Thirasia in the foreground

But, the sun did what it does (i.e. remain stationary while we spin and lose sight of it), and due to the steep sides of the caldera, it didn’t take long to be enveloped in shade. This was our cue to make a move.

But, rather than being dropped back onto the main island, we were instead treated to a boat tour of the caldera, visiting some unique little boatsheds that have been built into the cliffs, and if it weren’t for the vibrantly painted doors, you’d have no way of knowing that they were even there. It’s going to sound mad, but there was this part of me that kept feeling like I was back in Iceland. There was something about the landscape that felt familiar.

Even more exciting, we did a quick loop around the steaming volcanic core at the centre of bay. I’m not sure if I already mentioned it (no need to check, I haven’t), but Santorini is the remnant of a large volcano, with a giant circular caldera, with a few pieces missing from either side of the perimeter, and inside, the remains of the core. This is actually still quite active, and I read that the rising sea floor near the core was the cause for a fatal cruise ship accident that happened several years ago (off topic, but it’s still there, submerged vertically just below the surface after several unsuccessful recovery attempts).

The central island, which is actually an old and a new section of the core, is a little more than a giant pile of rubble. It almost looked out of place, as though it was a waste pile in a quarry – though, on a phenomenal scale.

In a testament to the present volcanic activity in the area, there are actually some hot springs in the ocean – but, it was in a small and busy cove, and we were told that it’ll make you, and your clothes go orange with the minerals in the water, though that wasn’t the reason we didn’t stop for a bathe.

We continued in our loop around the inside of the caldera, passing underneath the white concrete buildings that seem to cling to the tops of the cliffs like molluscs. It was a completely different perspective from below, realising just how high and steep the inside of the caldera is.

Rather than returning back to the main island, we all had a dinner in a small taverna (Agistri) in Thirasia. Even though it was just a short ferry ride away, it felt a world apart from the commercial hustle of the main island. There was none of the glamour, and not-coincidentally, none of the inflated prices. Dinner was simple, but it was all delicious, and as usual, I ate past the point of discomfort.

Even though I was exceptionally uncomfortable from my indulgent behaviour at dinner, I was still up for an evening stroll around Oia (ee-ya) – which started with a hike up countless (they’re numbered, and it’s only 260) steps. Side note – I was amazed, yet again, at how good the Night Mode on a Pixel phone is. I realise it’s all processing, however, I couldn’t make a photo from my DSLR look as vibrant – especially not handheld.

Anyway, Oia was such a rude awakening after the day of near quiet solitude. There were constant crowds of tourists making their way through the narrow streets, which seemed to only be lined with businesses that catered to tourists – souvenirs, restaurants, bars, and accommodation. It was clear that this was very much a town for tourists, but when it’s this pretty, I kind of tuned it out, and accepted my place in the problem.

Amazingly, I wasn’t feeling the affects of jetlag, so rather than an early night, we kept the evening going, joining with friends from earlier and trying some of the local wine (and cheese – because, I hadn’t already eaten enough). The cheese was delicious, but it was the wine that I’ll remember most. For such a small island, it was amazing the variety (and quality) of local wine. While not what they are most famous for (that’d be dry whites), I loved one of their dark reds, Mavrotragano, which was translated literally to me as Black Crunchy – and that is how I shall remember it, even if it will make no sense if I tried to buy it one day. And, then, because I was still functioning after a long active day, on what should be a jetlagged-riddled body, we all went and had shots.