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A To-Do List For Santorini, Greece

It’s always been on my list, so it’s kind of hard to believe it took me this long to get here. But a few years ago, as I started to plan out the last few ticks on my #30by30 checklist (30 countries by my 30th birthday), it seemed to fit in rather nicely just before the pinnacle 30th in Italy. I recruited my mom to join me, which was, as I predicted, rather perfect based on our shared passion for food, wine and walkable cities and we booked our flights to Santorini for a short, but oh so sweet, extended weekend of island life.

Why Santorini? Well, Santorini is what you picture when you imagine Greece. The white buildings carved into the cliffs. The blue domes that frame the iconic sunsets. Everyone who had visited there told me it was like being inside a postcard. And they were right. Of all the places I’ve been in the world, I’m not sure I’ve ever been anywhere more beautiful.


We had booked a rather modest hotel, affectionately named “Maria’s Place”. It was, unsurprisingly, run by a boisterous, Greek woman called Maria, who greeted us upon arrival at her small hotel, and lead us and our very big bags to our very small room. Inside this very small room, were two very small twin beds, side by side and an even smaller desk in the corner. This wasn’t exactly the luxury accommodation I might have imagined for our blissful weekend in Greece, but we got it for a wildly good deal (around $100CDN/night) by booking in advance, which was unheard of for this island, especially at this time of year, and we figured, how much time were we really gonna spend in there anyway? We giggled as we tried to open our very big suitcases into the very small corners of the room and poured ourselves some wine using the very small water glasses that were provided. Good enough!

With such a short time in Greece, we didn’t want to overextend ourselves, so we thoughtfully put together a short to do list of things to see, do and accomplish while in town. It went like this:

  1. Drink wine.

  2. Eat cheese.

  3. Get a suntan.

  4. Watch a sunset.

  5. Ride a donkey.

For those of you that know me, I am a bit of an overachiever and love a good checklist, and I am definitely my mother’s daughter, so by the end of Day 1, we had checked almost everything off. And by late afternoon on Day 2, as we rode a pair of donkeys through Fira Town, nervous laughter and road pops spilling into the cobblestone streets, we had done it all! And there was so still much more to see. We were still suffering the pains of jet lag, so we weren’t able to get up before 10AM any day (odd for both of us) and spent every evening sipping wine side-by-side in our little dwarf beds (as we came to refer to them as) watching movies on my laptop like school girls at a sleepover, so we didn’t do everything, but we have both said, we will undoubtably return. And if you’re considering a trip this way, stop thinking about it, and book it. You will LOVE it. And here, for your consideration is a more complete and thorough checklist (along with some helpful tips and hints) that will ensure you get the most out of your time there.

Drink wine.

But don’t pay 18 euros for a fancy pants glass of it the moment you arrive, thinking you’re splurging and treating yourself to “the good stuff” to kick off your holiday. It’s not necessarily the best stuff just because it’s expensive. And in fact, we found that that first glass that we paid out the a$$ for was probably one of our least favourite. (And trust us, we tried quite a few to be sure.) The Atlantis wine is served widely at local restaurants, and sold at local shops for maybe 11 euro a bottle and will do you just fine. If you do decide you want to try something else and/or take it up a notch, by all means! But be sure you ask to taste it first. And you know what goes great with wine?


Eat cheese.

If you haven’t heard of “Saganaki” before, then you’re just going to have to trust me. Or I guess you could Google it. It’s a very Greek dish that’s served as an appetizer (although I did order it for dessert once, which had the Greek servers staring at my sideways) and is essentially white cheese fried in oil and lemon juice and served hot, to be eaten with knife and fork. I know—it sounds weird. But it’s the best. And you simply MUST try it while you’re in town. Okay next up, you need to…

Get a suntan.

But beware of the sun here! It is HOT! And it will burn you. Always, always, always wear sunscreen. Especially on three-hour hikes across the island where there are no shady places to hide out and no shops to pick some up from if you forget. You’ll end up painfully aware of the burn settling into your shoulders and the hideous tan lines that are being created with absolutely nothing you can do to stop it, which is, I think, harder on you, mentally at least, than actually just getting a burn. Also, make 100% sure that your place has a pool. That is the most idyllic way to spend your days on the island, floating in the blue water with views of the Mediterranean surrounding you. And you’ll need it to cool off. Speaking of idyllic, be sure you also…


Buy a white dress.

I mean, we all fantasize about floating about in some picturesque scene wearing a flowing, white dress. And probably flowers in our hair. No, I don’t mean a wedding dress, I’m talking Under The Tuscan Sun stuff. And there is no better place to buy it than here. They seem to know and conveniently anticipate that we all have these fantasies, and therefore sell them everywhere you look. They’re not cheap, I’ll warn you, but if you’re standing at the till wondering whether it is really worth 100 euros to get to dress like the girl in your own fantasy, let me help you out. It is! Buy it. Then go curl your hair, put it on, pour yourself some wine and…


Watch a sunset.

Oia is said to have the very best sunset views. It’s also the quieter area (over Fira, the capital) and is generally more expensive. We stayed there, as I’d heard it’s the best. And I have no complaints about it, that’s for sure. But we did find that when we met up with some friends (serendipitously also on the island at the very same time) for dinner in Fira Town, the sunset was just as pretty as we watched it fall behind us during dinner. Fira, as it’s the capital, is a little busier, with more shopping, more restaurants and more tours running out of here. I wouldn’t be opposed to staying here next time around, as someone who does like a little action when I travel. Mom is sold on Oia, but insists she will get a normal-sized bed and a balcony with sea views (no more dwarf beds for Mom!). Regardless of where you stay, there is a bus that connects the two in no more than a 20-minute ride that costs you just a few Euros, so you can get back and forth easily. Or you can…


Hike the island.

Either from Fira to Oia, or the there way around. There is a trail that’s fairly well marked and the views are spectacular. It should take you in and around three hours, end to end, and while it’s not an advanced hike, it does have some uphill moments and you should dress appropriately (aka athletic flip flops won’t do the trick—trust us, we learned the hard way). You should also be sure to pack water, as you won’t find a shop for a full two-hour stretch and of course, as mentioned above… SUN SCREEN! If you’re doing Oia to Fira, you will reach a little place called Vanilia Restaurant just before the end of your hike in a town called Firostefani, which essentially the beginning of Fira itself, as they are attached. Stop in here, as you’ll be ready to get off of your feet and indulge in some nourishment, and be sure you…


Try all the Greek foods.

Saganaki, as mentioned above, is a necessity, but there is even more that you simply MUST sample while on the island. And this place is the best that we had on our holiday. Order the falafels (yum), the dolmades (grape leaves soaked in oil and wrapped around rice that are way better than they sound) and the moussaka (which apparently has a sauce in it with gluten—which I found out after—but luckily didn’t cause me any tummy troubles). Eat and enjoy the views, and then, a little further into Fira Town you can…


Ride a donkey.

Nuff said. It’s a must do and will be a memory we’ll certainly never forget. And I’m sure there will be others if you…


Explore more. 

We didn’t get to any touring on our short stay, but when we return, we’ll definitely be booking up some boat trips to the surrounding islands. There is a volcano, hot springs and the little island of Thirasia, all accessible within a day trip. And then hey, after Santorini, I’ve heard that Myknanos, Crete, Corfu are all pretty spectacular as well. Here are a few ideas for you: I guess I’ll have to add more to my list!


P.S. Be mindful of the surprising Santorini winds. They’ll get you. Or rather, your skirt, when you’re least expecting it. Case in point: during a photo opp with a view, in front of a terrace full of cocktail-sipping sunset watchers, while my mother stared into the dark, reflecting screen of the camera in an attempt to get a shot, and I stared off into the distance, somehow not realizing the force of the breeze I was feeling, I gave the crowd quite the show. And it wasn’t until later, when we reviewed the captured shots, that we saw the full flash of my lacy undergarments, in not one but FOUR of the photos. So yeah, that happened. Perhaps another reason you need that LONG white dress….




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