My Grecian Summer | The Insider Guide to Santorini

My trip to Santorini was amazing in all the ways I didn’t know it could be. This was my first time in Greece and in Europe, and it turned out a resounding success. Planning a trip to the famed Greek island? Use this post as an Insider’s Guide!


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You’ve seen it in the pictures: blue domes that standout against white buildings, pink and orange sunsets that take your breath away, and water so clear you can see right to your toes.

Santorini was one of my favorite vacation spots in Europe. Of the long list of things people must do when they visit, I did a little over half. After hiking up volcanoes, lunch on less populated islands, tubing at the black sand beaches and more, I can say my visit was as close to perfect as I’ve known.

This post is about my visit to the Greek Island. Use it to plan your amazing Grecian Summer!

Map of Santorini

Contents

Where I Stayed

During my booking stage, it was really important to me to have the traditional Greek Island experience. My priorities were white walls, oven cooked dates on thin bread, and local wines. My childhood was all Percy Jackson and Greek Gods, so all I wanted was to eat and sleep like they did.

That led me to booking a hotel in Oia, home of the famed blue domed cathedrals. It’s located at the Northwest end of the largest island. It took around 30 minutes to get there from the airport, and the town was beautiful. I loved the cobblestone paths and the homey vibe. It was more than a tourist destination – it was a place where people thrived.


There was a bit of chaos when we got to the edge of town. It was peak season, and a million other people had also just arrived, some quite frantic.

I’d learned during my layover at the Athens Airport that the Greeks are a blunt people – there was none of the sugar Americans so love to add to our customer service. Pair that with the stress of being in a foreign country and you’ve got quite the pot brewing.

I stood and watched. The hotel that I booked with was called The Arches. It’s exclusive, with only a few rooms, excellent staff, breakfast brought to the room every morning, and a dedicated concierge who stayed in contact with me from the moment we booked. I shared our drop off location with him, as vehicles could not drive through the town, and he came out to retrieve us. I couldn’t think of a better way to start my week.

On our 5 minute walk, Kyriakos gave me all of his tips for the best visit. Thanks to him I got to see the sunset on the first night – he told me to book a rooftop table every chance I got. Between the giant modern furnished room and my belly full of lamb, my first night on Santorini Island was one for the books.

What I Did

Watch the Sunset over Dinner

I didn’t know that Santorini was known for her sunsets. We searched for a rooftop restaurant that had space, not knowing what to expect. Luckily most of the incoming guests were still trying to find their hotels. I darted up the first set of nice looking stairs and happened upon a deck with a stunning view.

The ocean spread out in front of me – on the left side I could see the way the island curved, the smaller islands, and the center of the volcano. On my right the rest of Oia spread before dropping off to more ocean.

The wait was only 15 minutes. I sat at the bar and asked for something sweet and local – the bartender got my a glass of red wine that came imported from a nearby island. I sipped and looked in the direction of the sun with the other patrons. After 10 minutes, a collective gasp rose.

There’s something about the timing of the sunset, the way it passes behind the clouds and sinks towards the water that takes your breath away. These arrows of purple shot out over the sky layered in pink, and the orange sun slowly shifted to red. This feeling of peace and calm came over me, and I was so grateful that I made the trip. Just before she disappeared over the horizon, my table opened.

My Visit to the Perivolos Beach in Perissa

Day one started with breakfast delivered to my door at 8am (though I didn’t eat it – I was having a rooftop breakfast come hell or high water). The light was streaming in from the balcony that looked over the local homes, soft Greek music was floating on the wind, and there was not one single sound of tourism.

We checked in with Kyriakos to get his opinion on the best beach. He recommended a few, but told us we simply could not miss the Perivolos Beach in Perissa. It’s covered in black sand from start to finish, and the water was completely clear. The local businesses also had water sports available, so I was ready to go. We hopped into the taxi and off we went.

The beach was located at the southern edge of the island, clear water reaching all the way to the horizon. I thought I’d be able to see the coast of Africa from there, but it’s a bit too far.

The town was separated from the beach by a little road meant for walking and electric scooters. It was so cute, like a scene from Mama Mia. The white buildings glittered against the giant mountain behind it, while tourists milled about with drinks and ice cream. I had lunch at a swanky open restaurant – the biggest Caesar salad I’ve ever seen in my life, and a sweet margarita to wash it down.

There were hammocks for resting, chairs and covers. But I’m an active traveler, so I had to take a spin on the tube. You’ve heard of tubing – a floating tube attached to the back of a speed boat by rope. The waves were small and the driver’s one and only concern is flipping somebody into the water, so I had a pretty wild experience. If you love water sports, it’s the perfect beach day activity.

The rest of the afternoon was for resting and swimming. Here’s a fun fact about Santorini: since it was once an active volcano, there is no marine life in the water. No seaweed, no fish, no crabs. The water is completely clear and smooth as silk. The ground beneath is smooth as well – after a few minutes of slipping and sliding I decided to just tread water.


I watched the sun set from the ocean, collected a bunch of rocks since the natives said it wouldn’t curse me, and enjoyed the crunchiness of the black sand beneath my feet.

A Trip to Fira

Day two was for partying! The largest city on the island is Fira (also spelled Thira). That’s where many of the ancient sites, large stores and restaurants are.

But I went for the bars.

I spent the day wandering in the streets. There was shopping to be done, cathedrals to visit and more. My favorite site was Saint John the Baptist’s Cathedral. The blue and yellow stood out in the area, its soft yellow and blue warm and inviting.

The walk around the rim of the city was gorgeous. July in the Mediterranean feels just like Southern California. The sun is warm and agreeable and the wind is cool and sweet. The light glittering on the water brought tears to my eyes. I was happy to be alive then, and grateful that I had made the trip.

I had dinner at a restaurant called Vanilia, which was fantastic. Imagine soft Mediterranean strings and the smell of roses on the air while you sit on the edge of the rim. The drop went straight down, so we got a table on the second floor closer to the land. I had to order a gyro with a local white of course, but this place was on the fancier side and it came deconstructed. The sunset was different on that side of the island – orange and purple as opposed to the first night’s vibrant pink. The people in Santorini are lucky to live there.

The evening festivities brought laughter and joy. To be honest I don’t remember much after the second margarita. By chance we met a group of Americans who were from the north side of Chicago. As soon as I told them I was living in the Skokie area, we were joined at the hip.

We pregamed a small bar not far from Vanilia, and then poked our heads into a couple of the clubs. Now after a year of living in Europe I can say that you shouldn’t feel bad if you can’t get into the techno-pop vibe, especially for my Afro-Latinas and Americans. The glow sticks are cute from far away, but up close? It’s a different sort of vibe.

We ended up at Iriana Cafe Bar, a rooftop lounge just bougie enough for myself and new travel companions. And the music? Beyonce, Kali Uchis, and Michael Jackson. I spent the night dancing and laughing, making it back to Oia around 2AM.

A Boat Tour of the Islands

So here’s a fun fact about the Santorini island chain – it was once a massive volcano. Around 3,000 years ago there was an eruption that literally blew its top off and caused the center to cave in on itself. The giant crater was filled in by the Mediterranean Sea and the volcano became dormant, creating a beautiful Grecian puzzle set.


After brunch at this nice restaurant who’s name I forgot, we hopped on a bus headed to the docks at Fira. We had booked a boat tour to explore the other islands, and unbeknownst to me, hike to the center of the volcano.

Our American friends from the night before were crazy. After drinks and dancing, they got up around 4AM to hike from their hotel in Fira to Oia. They arrived just as I boarded the bus, and after closely observing their path I can say that European backpacking is not for me. However if you’re up to it, the walk from Fira to Oia is a very popular activity.

We made our way to the docks where what I can only describe as a pirate ship was waiting for us. It had giant masts, huge sails and rope railings all around the sides. It was rather crowded – getting a seat was all about dibs. But once we got underway, all I could focus on was the view of the cities from the water.

Oia, Santorini from the Mediterranean, copyright Amour Abroad 2021


The name of the smallest island in the center of the archipelago is Palea Kameni. This is where the actual crater is located – today it’s filled in with dirt and rocks. You can’t take any of the rocks with you by the way – something about Ancient Greek juju and the power of Zeus.

I didn’t know when we booked that we could actually walk to the crater, so I did my 25 minute hike in a sheer sundress and sandals. It turned out to be worth it though – my pictures were gorgeous!


The walk back to the boat was super quick. Our next stop was Therasia, the lease inhabited island. The total population there is like 500. We had two options: eat at the restaurants next to the docks or walk to the top of the island for lunch. It’s a 25 minute walk and I’m a “why not both” kind of girl, so we headed up for a quick meal.

I’m not too proud to admit I regretted my choice halfway through. The path is paved with pristine white walks that go up at almost a 45 degree angle, so much harder to climb than a mountain trail. I was stooped over by the time I got to the top, and because the Universe loves its little laughs, our whole group was met with tiny little European stairs to get to the restaurants. I almost finished a liter of water with my meal.

The boat works a bit like a cruise ship – be back at this time or you’ll be left on the island. We thought we were cutting it kind of close, but by the time we got back to the base of the island there were still 5 minutes left. And I couldn’t say no to Greek ice cream.

In total, the boat tour was an absolute blast, and the second thing I would tell you not to miss on your visit.

The evening bus brought me back to Oia where I rested and had a moonlit dinner. Oh gosh, I don’t think I was ever so sad to end a vacation or since. Santorini was so good to me, and I can’t wait to return.

Only next time, I’m island hopping on a yacht. Stay tuned.

Where I Ate

Here’s a summary of all the restaurants I ate at while in Santorini. Each one was set in a gorgeous location with beautiful views, excellent food and a packed house. Consider booking these in advance!

Pelekanos

This was the first rooftop restaurant I ate at on the day I arrived, and my personal favorite in Oia.

I just couldn’t resist a traditional Greek dinner on my first night, and since it came after a long day of travel I needed it to be hearty, too.

I started with a sweet local wine at the bar, and when we were seated ordered an appetizer of Greek bruschetta, made with ham, feta cheese and arugula on toasted bread. For the main course I ordered a leg of lamb that was drenched in sauce. It was sweet, tender, and nearly fell off the bone.

Tranquilo Bar

Somehow my Southern palate always catches up with me no matter where I go in this world. I was missing fajitas and quesadillas, and in dire need of a good margarita, so we searched for a nice American-ish restaurant near the beach. Lo and behold, Tranquilo Bar!

It’s such a cute vibe with the native Central American prints and Latin music. There are hammocks available, and when you sit outside you get a perfect view of the beach and the water.

For lunch I ate the largest mountain of a caesar salad I’ve ever seen and paired it with a delightful frozen strawberry mango margarita. It was one of those I-miss-home-but-am-not-quite-ready-to-go-home meals, and I adored it.

And a wonderful bonus for the bathroom: words of wisdom!

Santorini travel quotes
Terpsi n Oia

My travel partner found a gem with this one. Jet lag all slept off, I woke up and found my way to a stunning restaurant overlooking everything: the water, the islands, and the famous blue domed cathedrals. We could not have had better seats.

My breakfast was magnificent, a sweet and delicate balance of cream cheese, jamón and caramelized figs on a fluffy thin bread, covered in honey. And the drink, of course, was a Prosecco Mimosa.

Kayla Wilder in Santorini
Vanilia

The walk around the rim of Fira was beautiful and tiring, so I needed a restaurant that would allow me a hearty meal, breathtaking views, and was as close as possible to our next location. Enter Vanilia, a gorgeous two-tiered spot literally hanging off the side of the volcano. has the perfect combination of spectacular views and excellent traditional Greek food.

I was hungry, so I went with a classic deconstructed gyro and a local white wine. The scene was so gorgeous – the violins from the musicians at the church, the gentle wind carrying the smell of flowers, and the sight of the sun setting on the water.

It cannot be beat.

Apsithia Restaurant

Apsithia is very much a final night in Santorini sort of spot. This restaurant was deeply romantic, with views of Oia glowing under the moonlight. The picture below was the table next to us. Imagine beneath the town is a glittering blue-black Mediterranean Sea, and you have the full experience.

And the meal was sublime of course. I ordered stuffed mushrooms and pita with tzatziki sauce for the appetizer, which ran on the acidic side but paired well with my white wine. The main course was a fresh seafood linguine, and for dessert, a classic warm fudge brownie.

A Beautiful Conclusion!

I don’t think I could have asked myself for a better vacation. Everything, from the hotel to the meals to the people I met were spectacular. If you’ve wondered whether it’s worth it to visit the Greek island, take my word when I say you will never, ever regret it. Have the greatest time, and tag me in your photos!

Thanks for reading! I love you 🤍🤍


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