Santorini Escape

Quick stop on the ferry en route to Santorini from Athens. Shot on iPhone 6.

As our ferry departed Athens for Santorini, I could feel every second of hectic city life dissipate into the waves. We had a really big year, both emotionally and professionally, and I was looking forward to the future. But, before that exciting future, we had a vacation to enjoy. Every little moment.

Oia, Kamari and Meditations

Church in Oia. iPhone 6.

When you look at photos of Santorini with its white cliffside houses, steep steps into the Aegean and churches topped with blue domes, chances are, you’re looking at a town on the caldera side of the island – Fira, Imerovigli, or Oia. Oia is considered the most picturesque with its famous sunsets. Though unless you’re staying there, be ready to fight the crowds in an Instagram filled world. After touring the other towns, I’d say that Imerovigli, at the highest point of the island, feels the most resort-like though isolated; Fira feels like a fun party town; and Oia is a place to hide at your hotel to relax or shop if you decide to venture out.

As I get older, I’ve noticed my vacations have been filled more and more with museums, outdoor tours or hikes, and monuments and less with drinking in a park or just sitting on a beach. I blame this on a misguided sense of FOMO that as we age, we have fewer chances to experience the world and so, we “must fit everything in! In-for-ma-tion!” Except in Oia, we did a lot of sitting in our beautiful hotel, playing with cats that visited our doorstep and looking over the Aegean while trying to read more about Jason and the Argonauts.

This shot of Oia may look like a shot that’s hard to get, but in reality, the entire place was so photogenic that you could practically close your eyes, point the phone, and capture something like it. iPhone 6.

This break from the usual pace meant I felt a little more present-ness, a condition I have lacked for as long as I can remember. Wonderfully, after a long spell of not being able to write, I also opened up the laptop on our patio and started again. It is the perfect example of how slowing down breeds creativity.

Ironically, the topic that I couldn’t stop thinking or writing about was work. No, not specifics about jobs, career, deadlines or mistakes, but mostly about the value of work and my relationship with it. I had spent the last 6 years working in tech in Silicon Valley. Unlike 9/10 other people I meet in the Valley, I did not want to move to Silicon Valley to get a job in tech or to start a company. In many ways, my move to California was purely luck. After two rainy and dark years in London, I had vowed to go to the sunniest place on earth and found a job by responding to a friend’s post on social media. It looked interesting, it was for an industry I believed in (renewable energy), and most of course, it was in San Jose, California where it’s sunny on average 257/365 days a year. For the first time in my adult life, I decided to do something because it felt like the right fit instead of checking off the boxes. Soon after, my career and life aligned itself to move in a way that– up until this point – I had not experienced before. Things were smooth. I would spend the next lucky six years of my career in Silicon Valley, fulfilled and feeling for the first time in my adult life, that I had a found what I wanted to do: a mix between science and engineering, and most importantly of all, people, what motivates them, what they care about, and how they interface with technology.

The alignment I felt when I first moved to California was a magical thing, and here’s the surprise: it was neither easy to maintain nor did I face any fewer challenges than before. In fact, there were hurdles that were objectively far more complex and difficult than I had encountered up until that point. The key difference, though, was that instead of a dread and anxiety at failing the challenge, some part of me valued it regardless of failure because I knew that every moment spent trying to solve the problem made me one moment better at something I cared about. But just like that moment in Oia, this alignment had only happened after I took enough time to think, instead of optimizing frenetically without direction within the system that I had been in.

It was in this spirit I had decided – a few months before the Santorini vacation – to take a year for exploration, learning, traveling and slowing things down to become more creative. I left a job in an industry I loved for this sabbatical, and it wasn’t until that afternoon, sitting on the patio overlooking the blue sea connecting to the blue skies, that I put all those dots together affirmatively. I was hoping to grow, and I was lucky enough to get to a point in my life where taking a flexible year would work, something unthinkable even a year ago. What I wanted to do was to explore skill sets, technologies, industries, people and places, without constraints, deadlines or optimizations.  I wanted to talk to people (everywhere) about technology, and see (everywhere) how it was used, not just within Silicon Valley, within California, or within the U.S.

So as the sun rose and fell on Santorini, I felt with each passing day an excitement for a mysterious future ahead and one I hope is filled with moments to creatively wander.

Oia sunset from the castle. Doesn’t this look serene with the sailboat coasting into the horizon? No. Not serene at all. Not shown are the crowds that seem to have come from all over the world to sit at this one little corner of town. iPhone 6.

Beachside in Kamari. You need to purchase a drink at the bar on the strip to use the lawn chairs. Shot on iPhone 6.
Volcano tourism during our boat trip. If you use your hands and dig a bit, the ground is fuming hot. iPhone 6, shot by DMW.

Our Favorites


We were in Santorini in mid-June when it was warm during the day and in the sun, but windy and cool in the mornings and at night. In total, we stayed four nights in Oia and four nights in Kamari, and we filled our days planning outdoor excursions in the mornings, afternoon food tourism and evenings in the hot tub with wine. A list of all of our favorite activities are below.

Swim in Ammoudi Bay. Just off the edge of Oia – following the windy steps down (somewhere between 250 to 400 depending on who you ask), past the overworked donkeys, and past the white houses nestled against the cliffs – is Ammoudi Bay, my favorite swimming spot in all of Santorini. Once you walk past the restaurants and shops, you need to hike just a bit further (keep going around the edge of the jetty), to a lovely swimming hole. If you’re brave, you can swim to the nearby island and jump off into the crystal blue waters.


Boat tour booked by our hotelier at Aki’s Hotel leaving from Kamari (Blue Water Travel Agency). It was almost half the price of other tours and included all the trimmings like the Santorini volcano tour, a swim in the volcanic hot springs (well, more like warm springs but the swim out was fun), and visiting the island Kamara. Our tour guide was fantastic and spoke at least four languages, and my Company was able to fulfill his bucket-list dream of swimming in the ocean.



Sunset hike outside of Oia. My Company was traumatized by the frenetic-ness of our Oia sunset photos near the castle where he had seen a little old lady nearly fall off a cliff as she had nudged her way past the die hard Instagrammers (it’s a real risk in Santorini; you have no idea how dangerous it was to get that first sunset photo you see above). We decided a few days later that instead of waiting another two hours to get a spot and asking people to let us take our photo, we would do a little bit of hiking (~1 mile) outside of Oia to catch the sun setting over the city. It was well worth it. Plus, instead of waiting with the crowds, we got the privacy to do stupid stuff like the photo below shows. My only regret is not getting a bottle of champagne and a picnic for the view.

Wow, it takes a long time for the sun to go down in the summer! Had to find entertainment somehow. iPhone 6 by DMW.
Not bad. And no lives were at risk. iPhone 6.

We decided to run from Oia to Fira early in the morning (6-7ish miles over 2,200 ft of elevation gain) instead of hiking. Our logic (well, okay, it was my logic)? If we move faster, we won’t be caught in the heat. Our hotelier thought it was crazy and told her whole family. We ran with another equally insane tourist, a Canadian, whom we met on the road. But at least we got these incredible shots that we would have missed otherwise! As if that weren’t enough, we decided to hike to Santos Winery (2 extra miles each way) for a boozy lunch. I’m full of good ideas like that – who doesn’t want more dehydration with your dehydration?

Not shown: how sweaty we were.

Hiking to the Prophet Elias Monastery from Kamari (not for the faint of heart): Who looks at those switchbacks below and thinks, “Hey, I’d like to run this, maybe twice?” A sick, deranged person. I won’t name who it is. Also shown on our lovely run/hike is a cool cave (literally, it cooled us off since it was body temperature outside). Not shown: my fear in descending the mountain after we actually made it to the top of the monastery. Oh how the mighty fall.

Food & Drink

  • Santos Winery. This is on every tourist travel list, and I can see why. You get the full range of Santorini wines plus a view. Also, I can affirm that they’ll let you in even if you just ran and hiked 8+ miles over some volcanic mountains and still treat you like royalty. We stupidly kept trying to usher ourselves inside (ashamed of our attire in the very fashionable Santorini), when a lovely waiter showed us this VIP spot in the shade with the best view in the house. As a warning, a lot of the red wines in Santorini literally taste like volcano, because that’s what the grapes grow on. We loved the whites and sparkling, though!
16 might have been too much. How about some dehydration with your dehydration? Also, watch out for those dessert wines! They’re very sweet.
  • Melitini’s: Don’t order more than 3-4 plates, and don’t let the low prices fool you. It’s actually a lot of food, and the taste is authentic and truly excellent. I’d call it a gastropub favorite in Greece. We went there twice, nearly three times, but they were closed the third. (First picture on the left)
  • Katina Ammoudi Bay in Oia: You pay for the view but the fish is on point, and you get to select it in person. Also, our waiter was incredibly hospitable and carved out the best, hidden pieces of fish we would have otherwise missed. (Middle picture below)
  • Pita Gyros in Oia, our favorite fast food souvlaki joint. Also good for optimizing hot tub time when you stay at an amazing hotel.
  • Chinese food: KIWI on Kamari. Full disclosure: we went there twice. Shockingly for being such a small island, the food was very authentic and delicious, which made me realize that Asian food in Greece may be a real thing. This would come in handy in Athens.
  • Taverna Kamara: Boat ride lunch joint where you must (let me emphasize must) try the tomato salad (not the Greek salad) with island grown tomatoes. Because it does not rain on Kamara, the tomatoes grow from dew. Where else are you going to have a tomato bursting with flavor because it grew on a rocky, volcanic island fed from morning dew?
  • Captain’s Corner in Kamari and the dangerous ouzo from the “Captain”. We believe the Captain is the restaurant owner who walks around with a Coca Cola bottle filled with house-made-something-special. It may be ouzo, but we’re not positive. Don’t ask questions, don’t try to sip, just throw it back and say, “Kalismera!” Also, you would be wasting your time there if you didn’t get the lamb kleftiko. (Sorry, no photos for this one. We ate it too fast).


  • Angel Cave Houses in Oia (4 nights) and Aki’s Hotel in Kamari (4 nights). I’ll let the photos from the balcony speak for themselves for Angel Cave Houses.
One day, I’d like a hot tub like this one with those sweet coffee cup holders.
Not shown: How mad we were that we just spent 2 hours trying to capture the Oia sunset at the castle when we could have just come back to our hotel and seen this.
  • One thing to note here is that if you book directly with the hotelier, you can get a pretty good discount. We didn’t know before our trip, and next time, I’ll totally call the hotels despite not knowing a lick of Greek past ouzo and kalismera (it’s incredible how much English is spoken, though). Also, I’m a big fan of directly paying the hotels as they lose something like 80% of their earnings to taxes and fees, which go up every year.

Other Pro-Tips

  • Transit: If you must, take the buses! The buses, which are extremely cheap at 1.80 € each, run every 20 minutes and go nearly all over town including from the ferry when you first arrive which is 2.30 € (don’t let the private car shuttles fool you, though I always appreciate a good merchant hustle). They’re air conditioned and easy; you pay on the bus once you’re seated like a civilized person.
  • ATVs: You can easily rent four wheelers on the island, and I thought it looked really fun. My travel companion, however, hates most things that guzzle gas so we decided on public transit or hiking instead.
  • Don’t be afraid of a little bit of walking. You don’t have to be as crazy as I am, but the hikes are all well marked and full of beautiful sights. You may miss out on views like this one if you’re sitting on a bus or in a car.
  • Try to book a trip during the off season or sometime in the off-peak spring (March – May) or fall (October, November). Avoiding the peak season, July – September, can save a lot of money (>50%) and crowds.  Mid-June, while not traditional European holiday time, still felt overcrowded. Given Santorini’s popularity, more places will be open here than other islands during off seasons.


As we stopped to take this photo on our hike to Santos Winery, a bus full of tourists drove by, snapping pictures out of the window. iPhone 6.

13 thoughts on “Santorini Escape

    1. Thank you! I highly recommend it, and I suspect if you can go just a few weeks earlier than we did, you’d escape the crowds.

  1. I love this…I’m not sure I’ve ever read a blog. I’m an old fashioned woman…or just old 🙂

  2. Pan, this was so enjoyable and entertaining and insightful! please keep ’em coming 🙂 🙂

    1. Thank you for reading! I’ll try to be diligent this time (versus my usual once a year posts). We still go into restaurants and say, “Beef…that’s not even meat!” 🙂

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