Greece Part 4

In case you missed it, here are parts one through three before diving into part four:

Greece Part 1: The Planning
Greece Part 2: Athens
Greece Part 3: Paros & Antiparos

Even if you know next to nothing about Greece, odds are you've still heard of Santorini and seen images of its famous clifftop blue domes. Thanks to those blue domes backed by breathtaking caldera sunsets that make for great social media content, Santorini tourism is at an all-time high. TikTok is rampant with "what I expected" vs. "what I got" videos revealing extreme overcrowding and downright claustrophobic tourist conditions behind the scenes of those carefully cropped selfies. Plenty of reviews suggest it's not worth more than a day trip or to skip it entirely. We did our homework and tried to set realistic expectations, but ultimately decided that we couldn't spend two weeks in Greece without visiting one of its most iconic islands.

While in Santorini, we chose to spend our time exploring five places: Firostefani, Fira, Megalochori, Perissa, and Oia.

Getting Around the Island

Before I go any further, I want to explain the transit system in Santorini. While taxis/ubers were readily available unlike in Paros, much of the island consists of stone pedestrian streets inaccessible to cars. Ubering somewhere isn't as simple as calling a car to your doorstep and having it drop you at an exact location; you're probably going to have to walk a couple of winding blocks on either end of that ride. Because walking to a taxi felt about the same as walking to a bus stop but at a much higher price point, we opted to stick to using the public bus system.

My public transit experience is limited, but the bus system in Santorini is unlike any other I've seen. Instead of various routes with multiple stops where you can hop from one line to another, every single bus in Santorini starts or ends in the central town of Fira, and there are no midway stops. Think of Fira as Point A and all other towns as the rest of the alphabet. You can go from Point A to B, A to C, A to D, etc. But if you want to go from Point B to C, you first have to go from B back to A, then A to C. It's a simple system with no routes more than 20 minutes one way, but it can be time-consuming if you're trying to hit multiple destinations in a day. At around 2 euros per trip, we accepted the minor inconvenience and planned accordingly. 

Firostefani: Our Home Base

Having done our transportation homework, we chose to stay in a town called Firostefani which is about a 15 minute walk north of Fira. Spoiler: not all 15 minute walks are equal. As someone that lives in a completely flat city, I always conveniently forget to factor in hills and elevation when I'm looking at a map for walking distance. Our 15 minute walk was entirely downhill...until the walk back.

We took our time choosing a hotel, and I'm glad we decided that it was worth a slightly higher price tag to book somewhere with an unobstructed view of the volcanic caldera. I saw so many beautiful sunset photos from the island before visiting, but what I didn't realize is that most of those views come with a price tag and belong to hotels, restaurants, and local homes. There are limited free viewpoints and those become crowded quickly at sunset, so having access to a small private hotel was perfect.

Case in point, the view from my bed:

The weather was awful the day we arrived, so we spent the first night holed up in our room playing Taco Cat Goat Cheese Pizza (a card game for ages 7+ that will have your entire friend group in tears when you realize that you are collectively incapable of performing the Narwhal card). Eventually we braved the rain for dinner at Aktaion, the island's oldest restaurant, and were treated to the best calamari and lamb shank I've ever had in my life. It was totally worth the 15 minute uphill "walk" in rain and what had to be 20+ mph wind gusts.

On our third night, we finally got to take full advantage of our accommodations and camped out at the edge of the hotel pool for a stunning sunset. I knew Santorini would be windy, but nothing prepared me for the bone-chilling feeling of that wind in the evenings. I started the afternoon by the pool only slightly chilly in my bikini, but by the time the intense sun began to set, I was in a long dress with leggings, socks with sneakers, two jackets, a blanket, and my hair in a bun because the artsy windblown instagram vibes quickly devolved into "if I keep my hair down for more than 30 seconds, we're going to be cutting these knots out later." Freezing realities aside, I couldn't help myself from snagging a few of those picture-perfect tourist shots.

The view at the Villa Ilias Caldera Hotel

While we're on the topic of getting perfect social media content in Santorini, we were treated to an unexpected view during this sunset that I simply can't leave out. For context, our hotel was next to an empty lot secured by a pointy iron fence several inches taller than the average person. At some point while seated by our pool, I noticed motion out of the corner of my eye and turned just in time to see a young woman hopping the fence. This made little sense to me because the bars were easily wide enough to slip a phone through and take great sunset photos. Unable to ignore the petty crime suddenly unfolding behind me just as much as the breathtaking sunset before me, I found my attention divided between the two.

By the time the tresspasser removed her pants in full view of the public street, I stopped trying to guess what would happen next and accepted the fact that I was clearly experiencing one of those "wtf is going on?" travel stories that is sure to yield at least three paragraphs of blog space.

What happened next is she changed into a mostly invisible thong and a see-through mesh mini dress, set her phone up on a tripod, and proceeded to record, idk, racy exotic dance TikToks? Bougie Onlyfans content? This went on for about an hour, and at one point I started taking a video of the sunset in front of me and flipped to selfie mode for a few seconds for eternal proof of my two contrasting views. I don't know what I expected, but it wasn't the full body gyrating against the concrete ground visual that I got. I certainly captured my own "What I expected vs. what I got" memory, but probably not one I can share here visually. I'll sum up the mental image with a much more family friendly description: There was a gorgeous sunset in front of me, and an unexpected view of the full moon behind.

Let's be honest, I can roast this girl's influencer spectacle for entertainment purposes, but she was gorgeous, has far better coordination than I could ever dream of, and probably has a million followers and paid subscriptions while I write about her to an audience of approximately seven Hanson fans. She also had some serious guts to scale the pointy fence and had to be absolutely freezing in that outfit. Honestly more power to her; I probably looked just as ridiculous in my own way, silently judging while sipping poolside hot chocolate and dressed like a baked potato.

Megalochori & Perissa

In addition to our stay in Firostefani and frequent walks to Fira, we made a quick trip to Megalochori to see "the heart of Santorini" followed by lunch in Perissa.

Megalochori was a bus ride to what felt like the middle of nowhere followed by a short dusty walk to a stunning elevated view of the island. You basically start at the top of a cliff and can choose to trek down a fairly steep incline to reach the famous heart of Santorini (which was pretty cool, but did not look like a heart from any angle we tried).

From there we took a bus back to Fira, then boarded the bus to Perissa which is famous for its black sand beach formed by volcanic ash. My lunch of fish and chips was probably my least favorite of the trip, but naturally a cat appeared and offered his assistance, so it didn't go to waste. We didn't do any swimming, but it wasn't very busy and would have been a solid place to relax without a crowd if we had planned to stay longer.

Oia (pronounced "ee-ya")

I've saved Oia for last for two reasons: one, it's the main tourist destination in Santorini, and two, we booked a sunset catamaran cruise that started and ended there.

First, Oia is everything social media led me to believe it would be: picturesque but overcrowded. Bonus points for also being overpriced. The main path from the bus to the maze of shops and houses got narrower and narrower, probably no more than six feet wide in some areas. It was so packed that we were shoulder to shoulder with everyone and barely crawling along at times. If this was the off season, I can't imagine the utter misery of being there in the summer when it's hotter with more people. I'm glad we got to see it, but an hour was long enough to get our fill of trinkets and photos. I'm convinced that everyone saying to skip Santorini must be spending all of their time in Oia.

The Mediterranean Sea

Our catamaran cruise was supposed to take a different route starting at the southern part of the island, but we got a last minute notice that we would need to follow an altered itinerary due to weather. I'm so glad we declined the option for a refund and took our chances on the altered route, because it ended up being one of my favorite experiences of the entire trip. It was also the perfect way to escape the crowd in Oia.

We left from the picturesque Ammoudi Bay around 2:30pm, accompanied by a group of 15-20 passengers, mostly from various U.S. states but a few from Mexico as well. I remember thinking that it was nice that we all seemed to be in a similar age range, only to later be hit with the unpleasant realization that everyone else was probably mid to late 20s and nope, that makes us the old ladies of the boat. I must be in denial.

Our abbreviated itinerary included a stop to swim at the volcanic "hot" springs, which I am putting in quotation marks because it was literally the coldest water I have ever felt in my life. I'm often the cold person sitting poolside at BTTI while all of my friends swim, but I wasn't going to miss out on the opportunity to swim in the Mediterranean Sea. I grabbed a pool noodle and forced myself to be the first one brave enough to take the freezing plunge. One by one, everyone followed, and we all had a good laugh at our shared trauma. It got better after the initial shock, but I wouldn't even say I got "used to" it. I think I genuinely went a bit numb. 

The cruise included a delicious dinner followed by a trip back up the coastline to watch the sun set over the water. It was gorgeous even through a few storm clouds, and I feel so fortunate that we somehow managed to make it happen in between bouts of rain without any fails along the way. The boat was immaculate, the company good, and the staff friendly. I can't recommend it enough if you ever find yourself in Santorini. We ended up with Sunset Oia booked through Viator, but there seem to be tons of great options to choose from.

Final Thoughts About Visiting Santorini

If you're considering a trip to Greece, I'd say don't skip Santorini, but don't go into it blind. 

• If you have any sort of mobility or physical limitations, research accessibility and transportation proximity before you go.
• Arrange private transportation for arriving and leaving. Buses were great for getting around without luggage, but I absolutely could not have handled dragging even my carry on suitcase uphill from the bus station.
• Bring motion sickness medication even if you're normally fine. The drive from the port into town is a zig zag formation at a steep incline up the side of a cliff.
• Leave the cute shoes at home and embrace the Tevas, the Hokas, and whatever chunky old lady shoes are going to keep you upright.
• Pack a windproof jacket and skip the short dresses because they are going to fly the wings of an eagle and glide along with the wind, very high. People will definitely be thinking of you when your dress hem is up to your ears. 
• Of course, there's always option B: Do pack a very short dress, hop a fence, and start funding your next trip.