our day trip to oia, santorini


The whole week Porter and I were on Serifos and Folegandros we went back and forth about whether or not we should take a day trip to Santorini. I had never been, so I was all in favor, but, at the same time, day trips when you already live a full-time traveling lifestyle can be exhausting…and expensive. Up until the day before we went, we were fluctuating. A windstorm hit Greece pretty hard last week, though, so the weather had been iffy for about five days in a row with no signs of clearing. We were a little bit restless. So, we decided to bite the bullet. We knew it would be a very long day (with about a two and a half hour ferry each way due to the weather) and we knew it would probably be hectic when we arrived, (we were going on a Saturday) but we also knew it was a place we wanted to tick off having photographed, and I wanted to tick off having seen (Porter had already been once on a family vacation). Sometimes, you just have to say screw it, this day is going to be exhausting but worth it, and sometimes, fate uses that as an opportunity to see just how much you can handle…


I want to prelude outlining how our hectic day in Santorini unfolded by saying, even still, it was absolutely worth it. I’m so grateful I had the chance to see Oia, walk those streets, point out places in real life I’d been scrolling through on Instagram for basically years at this point, and to just absorb what has to be one of the most visually stunning places on earth. In my head it was like Monaco colliding with Macchu Picchu – so much taste and culture and style, and such sketchy heights! But, here’s the honest truth: even though it was gorgeous and amazing, sometimes you are simultaneously grateful to be somewhere and ready to call it a day…and that’s how we felt about Santorini. Here’s why…


Our whole time we’ve been jumping from island to island in Greece we’ve been moving via ferries. These boats are ginormous, most of them have escalators inside, a few stores, one even had an arcade for kids and a playroom. They’re more like floating airport terminals then the kinds of ferries you hop to The Vineyard over the summer. When we woke up to leave for our trip to Santorini, this is the kind of boat we were expecting. Unfortunately, it wasn’t what we got. We’d accidentally booked a smaller speedboat without realizing, one with a catamaran-style bottom and seating plan that was absolute mayhem. Our ride over we were packed in like sardines, hitting every single roller at an angle that sent your stomach lurching again and again. Most people couldn’t figure out their assigned seat, and it felt like a game of musical chairs where the floor was tipping every which way and the language barriers between all the tourists from every corner of the world led to a Tower-of-Babel situation where people just generally didn’t know what anyone else wanted from them. For whatever reason, I had a serious bout of claustrophobia and made Porter hold my hand the entire time, even though I’ve lived at sea before, and have experienced a whole lot of rough water (I honestly think it was just the amount of people packed in). SO lesson learned, know what boat you’re booking because 9 times out of 10 you have the chance to take the kind of monolith we’d grown used to, but then there’s that 1 time that maybe you can’t and, if the weather is kind of terrible, you should wait a day if possible. It was chaotic, but doable, probably a four out of ten experience, but definitely not bad enough that we would let it seep out into spoiling the rest of the day trip.


We arrived at the ferry terminal a little bit shaken up, but excited to see Santorini. I pushed the reality that we were going to have to take the same boat home five hours later into the corner of my mind and we hopped a cab and arrived in Oia about a half hour later. Immediately, I knew that it was worth the hype. This place is incredibly incredibly cool. Porter and I spent the first hour and a half just getting our bearings, figuring out where certain things we wanted to photograph were, and ambling up and down all kinds of steps and mini side streets only to walk by an adorable cafe or a miniature pool in a cave with an unreal city and sea view, or to run into a donkey on its way up or down a million steps with or without a passenger. There were lots of tourists, there were lots of selfie-sticks, there was the occasional shove, but all-in-all it was what you’d expect on a Saturday, and because of the way the city is laid out it isn’t that difficult to find quieter areas, little streets that somehow have been overlooked by the streams of people and are just quietly waiting for you to walk by and do a double-take before exploring them. We got a big bowl of greek yogurt with honey and fruit at a tucked-in cafe (which they serve in ice cream bowls here with long spoons, the way you would a sundae) and even though I was a little nervous about the ferry ride back, we had a great time. We took a million photos, Porter managed to scramble onto some rooftops we’re almost certain were forbidden to walk on, and we found ourselves back in the taxi headed toward the ferry terminal five hours later feeling like only twenty minutes had passed. We both had that kind of “wow, I could fall asleep where I’m sitting (the stairmaster has nothing on Santorini) but I know I’m going to be so happy we did this tomorrow” kind of feeling.


It wasn’t a perfect day, but it’s definitely a memory we’ll hold onto. The ferry ride back wasn’t any better than the one over (to be honest, it was delayed two hours and significantly rougher), BUT we collapsed into a heap back on Folegandros, ordered some room service tea (funny how that kind of cures everything) and kind of shrugged and said well, that wasn’t an ideal day but worse things have happened.


Porter said to me walking through Mykonos last night, it’s so weird how with what we’re doing right now even the bad days are good days. We had kind of hectic night last night with some camera issues (blog post to follow) but it actually turned out being a really fun night in Mykonos, and we walked around talking about that subject for a while. When you like what you do, bad days really aren’t that bad. In fact, the bad days are kind of motivating in the way that you become a better runner on the days you push yourself because you feel like stopping more so than on the days that it comes naturally. There’s a pride and something really real and kind of physiological I can’t quite articulate to the way you feel when you felt pushed to your limit but still maintained the kind of attitude you want to be capable of. I’d so much rather have another never-going-to-end, I-can’t-handle-this day doing what I love than an I-checked-all-the-boxes-and-can-go-home-and-check-out kind of life. I know this isn’t everyone’s mentality, and I also know there isn’t a right or wrong when it comes to opinions on that sort of thing, but I also know I’m so grateful I ended up with someone who feels the same way I do.


Santorini, we will be back. But next time, I’m taking a plane.




Anna Lisa & Porter




  1. Christos says:

    here is how to visit santorini on perfect weather https://www.visitgreece.com.gr/en/members/travel-blog/item/622-santorini-weather-guide.html, info on how is the weather all months of the year.

Comments are closed.

subscribe to recess city:


  • Wearing a top made out of recycled plastic a bracelethellip
  • Sharing a bit more on who we are amp whathellip
  • Travel is the most beautiful way to realize what ahellip
  • One of the questions I like to ask myself beforehellip
  • Were not going to ever be able to achieve thehellip
  • Were gearing up for flying halfway around the world inhellip

Brands We Love


Girlfriend Collective                                     Soko                                                   DL1961                                                         St. Agni Studios                                           Reformation                                                 Rode to Nowear                                                  


Nisolo                                                   Scotch & Soda                                       Cotopaxi                                             Mews                                               Alternative Apparel                                     Thinking Mu