An Insider's Guide to Santorini, Greece with Maria Giannetos

Where does one go to escape the chilling temperatures of Chicago? For Windy City-based blogger Maria Giannetos, it's a no-brainer—Santorini, Greece. With a heritage rooted in Greek culture and a soft spot for Santorini's peachy sunsets, picturesque views, and seafood pasta, Maria recently embarked on her 14th trip to the island-dotted country. Ahead, go on a virtual tour of Greece with Maria's foolproof insider's guide to Santorini including tips on the best of neighboring cities Fira and Oia.

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I think this was my 14th or 15th time visiting Greece. My family and I have been traveling there either every summer or every other since I was born. It’s truly the one place where I feel the most myself and the warm memories are what get me through the harsh Chicago winters while I'm seven inches deep in snow. My dad's family is from Kalamata—like where the olives grow—and my mom is from Cypress, which is an island right off of Greece. Both are so incredibly beautiful in their own way and I would recommend either to first-time travelers in a heartbeat. Absolutely everything in Greece inspires me: my family, the culture, being surrounded by ancient history and art, the graffiti, the food, the hospitality, the humanity. It’s all so incredible. 

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I always stay in both Athens and Kalamata every year and then go on little side vacations to other cities and islands while I’m there. This year I also visited Santorini for four days with eight other girlfriends. Both Fira and Oia are extremely touristy, which I don’t usually love, but the beauty of both cities made up for it. You can get lost in the narrow, winding roads lined with little shops, restaurants, and bars. Oia is where everyone goes to watch the sunset, and once it gets dark, everybody leaves to hangout at the bars and clubs in Fira. The streets of Oia are packed with people to the point where you can’t walk through without touching shoulders with five people at the same time. Once the sun sets though, everyone is rushing to leave and get to their next destination. 

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The most noteworthy part Santorini’s culture, and probably what it’s most known for, is its architecture. The white-washed homes and blue-domed churches are so iconic that they are what most people think of when they think of Greece, although these features are really only shared by islands in the Aegean Sea. Many residences in Santorini are literally dug into the volcanic rock and are known as cave homes. Even though most houses and buildings are painted white and blue, the island is still vibrant with color, be it pops of fuchsia from the bushes of bougainvilleas or window shutters painted bright red.  

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Beauty Packing List

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Fashion Packing List

Two things come to mind when I think about my packing list for Greece: white and linen. I actually found some really cute and affordable pieces at for Forever 21 while last minute shopping. I loved the idea of long trousers or wide leg pants, but it was so hot. I lived in these two Madewell denim mini skirts while I was there. They go with everything and can be casual or dressed up for a night out. I don’t know how I did it, but I packed four days worth of clothing, shoes and beauty products in the smallest little carry-on. It was the only thing I had with me other than my huge suitcase I had brought with me to Greece from Chicago. I would be lying if I said I didn’t sneak a few items into my friend's luggage that wouldn’t fit in mine.

I had already been in Greece for two-ish weeks, so our flight was out of Athens. It took literally 25 minutes to fly into the Fira airport, so shorter than my daily commute to work in Chicago. So I definitely recommend carrying-on rather than checking in luggage considering the flight is so short from Athens - it’s so much more convenient! Just make sure all of your liquids are under 3.4 oz. 

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Booking the Trip

We used hotels.com! There are so many cute boutique hotels on the island, but looking them up on Instagram and seeing photos that people have taken helped so much in deciding where to actually stay. 

Where to Stay

We stayed at the cutest family-run hotel in Fira called Evgenia Villas and Suites. It was about a five-minute walk to the main center of Fira, which was actually really nice because it gets a bit noisy over there at night. Our area was much more peaceful but still close enough to everything around Fira. 

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Dressing the Part

For sure bring comfortable walking shoes! You’re definitely going to be walking a lot, and the roads in both Fira and Oia are cobblestone and sometimes really steep or have a lot of steps. I brought a pair of high heels that I never even took out of my luggage. It’s also extremely windy, so I would rethink any short, flowy dresses. 

Getting Around

Donkey! Kind of kidding, but also not. There are actually companies that offer donkey rides that can get you from Fira to Oia in about two hours. We decided to just rent a car and do the ride in under twenty minutes. Another really popular method of transportation around the island is four-wheelers. Honestly, driving one of those things cliffside to get from one city to the other looked absolutely terrifying - but if you’re up for it, definitely try it out. If you’re staying in one city for the day, the best method of transportation is walking.

Tip for First-Timers 

Don’t worry about the language barrier. I went to Greek school for ten years, but my Greek is still pretty rocky. I was actually really excited to practice, but the area is so saturated with travelers from all over the world that literally everyone speaks English. Also, you absolutely must go to Oia for the sunset. It's breathtaking, but get there as early as you can so you can snag a good viewing spot! In my head I was thinking, “Okay, it’s a sunset, you can literally see it from anywhere” but there are definitely better places to settle in and get comfortable.

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DAY 1

10AM Our plane landed at around 8AM, so while we waited to be checked into our hotel room, we ate breakfast in the little breakfast room of our hotel. It was right off of the pool with an incredible view of the cliffside. We sat there eating the complimentary baked goods and read up on the best places in Santorini with travel books our concierge gave us. 

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12PM For a quick lunch, we walked into the city to grab something we could eat on the go. We were told that the best place to get a quick gyro was this little hole in the wall called Lucky’s. A chalkboard sign with “Best Gyro in Santorini” greeted us at the entrance. It was packed with people and extremely hot given that the restaurant was basically just the kitchen with no AC. However, the pork gyros was DELICIOUS and probably one of the cheapest meals you’ll find on the whole island. 

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12:30PM Gyros in hand, we walked up and down the cobblestone streets of Fira which are all lined with stores, from little tourist shops to beautiful boutiques. There’s no way you’re able to go into every shop, but I totally could have if we had the time. They were so fun to browse through and each one was so different from the last. I completely fell in love with this 500 euro purse by the Greek brand V&R - I’m still thinking about it.  

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2PM There are a few famous beaches in Santorini, and we intended on seeing all of them, but by the time we had climbed down to the ocean at the Red Beach we decided to stay for the day. If you like kind of roughing it at the beach (laying on your towel, not in a shaded cabana) you’ll love it. It’s definitely one of the most unique beaches I have ever been to - the red and black volcanic stone is so striking against the blue water. 

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5PM Does the sunset count as a historical sight? I’m the type of person who will stop and watch the sunset wherever I am. I’m always so mesmerized by the oranges, reds, and purples in the sky. I truly didn’t expect the Santorini sunset to be much different than any other sunset, but I was so wrong. Not only is the actual sunset amazing (the sun seriously looks like it's melting into the ocean), but the entire city becomes engulfed in a peachy haze that reflects off of the whitewashed city. It's SO beautiful. You’ve never experienced this kind of light before.

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8PM While we were exploring Fira, we were also scoping out restaurants that would have the best view of the sunset during dinner. We ended up making reservations at Classico, which had both an incredible view and great food. They didn’t have any traditional Greek dishes, but the menu was definitely seafood focused, which I loved. So yummy. 

9:30PM We went out to Koo Club in Fira! It was so fun and the DJ played really good music all night! It's a pretty big place with both outdoor and indoor spaces, so it never felt too crowded. It’s also open from 11pm to 6am…need I say more?

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DAY 2

11AM We spent all of our second day on the island in Oia. After a quick Google search, we found another great cafe with an amazing view of the city. After climbing a very steep staircase, we made it just in time for brunch at Terpsi. We were craving an American style breakfast, so we all ordered omelets and split french toast. The waitstaff was extremely friendly and even moved some tables around so we could have a clear view. 

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1:30PM One of my personal favorite evenings was the one we spent at Santos Winery. When we called to make a reservation, we had originally planned on making it for earlier in the evening, but the host suggested we come no earlier than 7:30. We had the most beautiful view of the ocean and arrived just in time for the sunset. The menu was full of different wine flights and little bites - I ended up ordering a flight of five different white wines which were all incredible. The most standout, however, was a dessert wine called Vinsanto. It literally tasted as sweet as honey! 

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3PM Not exactly a historical site, but one of the most visited shops in Oia is an incredible book store called Atlantis Books. This was one of the few places that every single person I asked for Santorini recommendations mentioned to me. They have an amazing selection of books, and even have a few first editions of classics that were being sold for hundreds of thousands of euros. The story behind the bookstore is so charming: in 2002, Craig and Oliver traveled from England to Greece and spent a week in Santorini where they noticed that the entire island lacked a bookshop. They opened Atlantis Books in the spring of 2004 and have been selling all kinds of books to tourists and locals ever since. 

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6:30PM We really only wanted a quick bite before heading to find a good spot to watch the sunset so we had dessert for dinner. There are probably hundreds of ice cream and gelato places in Oia, but the best by far has to be Lolita's Gelato. Order hazelnut in a waffle cone and don’t look back. 

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8PM Tango in Fira was my favorite bar we went to while on the island. It was so cute and was made to look like it was built directly into the volcanic rock like the classic cave houses of Santorini. If we hadn’t only gone at night, I would have taken a thousand photos there. The drinks were so good and the crowd was always fun. 

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