The Crafty Traveler

Santorini can defeat you. It is without a doubt one of the most tourist driven destinations in the world (hope you aren’t claustrophobic). Cruise ship passengers populate the pathways everywhere you walk (I never counted less than 3 docked ships on any given day). The prices are astronomical, from the hotels all the way down to the Aperol Spritzes. I can easily describe this island as a bit of a fishbowl, but I can also easily describe it as one of the most beautiful places on earth. There’s a reason these issues exist. You must visit with the right mindset.

There are certainly ways that you can minimize some of these issues. The time of year can be a big help (I would highly advise avoiding Summertime, shoulder seasons for the win). You can stay outside of hot spots like Oia (those blue domes are like moths to a flame for tourists). However, some of this you just have to embrace. It is not the place to travel when on a budget. In fact, it’s one of the few places I would say splurge for as nice of a room as you can afford (so that you can spend your afternoon there while the crowds cruise around). You are going to have to book as much as you can, as far in advance as you can (that’s where I come in). Lastly, just embrace the fact that you are a tourist that will be bumping shoulders with other tourists. Just do so with respect to the place that you are in, and it will respect you back.

I have seen many people spend a week in Santorini, which I think is too long. In fact, I think Santorini should just be one small part of your trip. If you are going all this way, make it a priority to visit other lesser-known islands (don’t worry, future posts coming on that). I also know people that have only seen Santorini through a cruise ship. While that will give you a taste, the mornings and evenings while people are on the boat are my favorite times on the island (plus, the caldera views are better from above). For me, 3 days is a sweet spot here, so let’s set you up for success.

Spend your first couple days outside of Oia in either Fira (if you want somewhere a bit busier including nightlife) or Imerovigli (if you’re looking for a quieter more romantic vibe). Either way, you want a room overlooking the caldera, with your own pool to soak it all in (again, the splurge makes a huge difference here). If you go with Fira, check out Enigma Suites (the exclusive or signature jacuzzi suites in particular). If you go with Imerovigli, look at Grace (honestly, there are so many incredible cliff tops hotels to choose from). On day one, check in and chill (that’s the least busy itinerary you will ever see from me). It’s likely been a journey to get here, so time to soak it all in. At some point, hunger will likely creep in. No matter which of these two spots you are posting up in, your dinner spot is within reach – Aktaion. Book ahead for an authentic and traditional, family-run taverna meal (which is not super easy to find on this island). If you did end up staying in Fira for the nightlife, there are plenty of night clubs to dance the night away, although you’re more likely to catch me with cocktail in hand – Stoa Bar to the rescue.

Day two is all about the wine (remember who you’re dealing with here). Santorini has a high-level wine culture for how small it is. There are a couple of pods of wineries you can spend your day visiting. I like starting the day at Venatsanos. Book a tour to check out the gravity fed system and tunnels that lead to a cliffside stunner of a tasting. From here, it’s over to Gavalas for the rare and premium tasting to try varieties of wine you won’t find anywhere else. Time to fuel up before round 2. Take the ten-minute walk over to Steki for souvlaki that will hit the spot. Time for pod number 2. Estate Argyros is waiting for you with modern digs providing a perfect setting to learn more about the vine training system of Santorini. To ensure you hit all types of wineries on the island, wrap up your day of wine at Art Space Winery, the understated opposite of Argyros. Dive into the history of this family-owned spot while sipping alongside the abundance of art that surrounds you. If your liver in still intact, check out the tiny but powerful taproom of Santorini Brewing Company (and if you don’t get here, try all of the different “Donkey” beers around town during your trip). On a beer side note (I can’t help myself), Ftelos Brewery is also worth a stop for a modern take on Greek craft beer at an impressive facility.  Cap your day with dinner at Metaxi Mas (hopefully lining up for you at sunset). A cozy hilltop spot that hits you with more of that authentic goodness that you came to Greece for.

It’s now your final day, and you are heading into the lion’s den – Oia. As I said it’s no doubt a tourist trap, but that’s for a reason. You need to experience one day here. A strong strategy would be to stay somewhere on the other side of the town center, and Armenaki is exactly that (another spot to splurge and get that private plunge pool). I wouldn’t blame you if you wanted to spend most of your day here. If you do venture out, burn some calories and take the hike down to sea level and hit up Dimitris Ammoundi Taverna for lunch. Yes, you could take a cab, or a donkey at that, but the octopus that was caught that morning is more rewarding after you break a sweat. If you are exploring town in the afternoon, hit up Boozery Bar for fun cocktails to go, Lolito’s Gelato for a treat, and Pitogyros for the kind of gyro you’ve been searching your whole life for. For your final night, warm up with a cocktail at Hassapiko Bar before dinner at Oia Vineyart. Yes, you could overpay for a restaurant with a view, but you will walk away more satisfied with tasty tapas and the extensive wine list this spot serves up.

You did it. You conquered the crowds of Santorini (and hopefully you now agree with me – it is worth it). Sometimes these kinds of destinations disappoint, but I find if you come in with a plan and a positive mindset, you leave revering a place versus regretting it.