Santorini & Mykonos Greece Travel Guide

Day 1 – Leaving Chicago & The USA Behind

The day our flight was scheduled to leave, it was raining in Chicago. We were just dropped off at the gate of O’Hare International Airport by my sister and we then found out at the ticket counter that the plane was going to be delayed. We were told that the plane could not take off at the scheduled time because of the approaching storms.

However, when we were told it was going to be delayed two hours, we immediately realized we would miss our connecting flight in Philadelphia. No bueno!! We quickly asked the ticket counter associate to see if there was another connecting flight. There wasn’t another flight going to Philadelphia…until tomorrow. With a little bit of luck and a lot of patience, the lady at the counter was able to find us a flight to London later that day that had a connecting flight to Athens the next day.

So, instead of gambling on our plane to get fixed, we chose to re-book and head to London. We had about a half of day to kill before the London flight, so we headed over to the nearby shopping mall to kill some time.

We arrived back at the airport via Uber to head through security and wait at our gate. The original plan was to get into Athens around 9am 24hrs later and visit the Acropolis, Parthenon, Plaka and local taverns to eat, drink, etc. Unfortunately, that didn’t happen, so we missed our entire day in Athens. After what felt like the longest delay ever, we boarded our overnight red eye to London around 11pm Chicago time.

I slept for most of the flight and woke up just before landing in London. It was the next morning now and we arrived in anticipation. Our flight for Athens was in a few hours and we had time to kill again. There is not a lot to do so I wrote an article for the blog titled “Top 10 Carry-On Items”. Check it out!

Landing in Athens, Greece

We ended up getting into Athens International Airport (ATH) “Eleutherius Venizelos” around 7:45pm and by the time we grabbed our luggage and hoped in the taxi to our Airbnb apartment, it was around 9pm. We found a local place to eat near the apartment that served us some souvlaki, homemade fries and a tall glass of Mythos (popular Greek beer). The souvlaki was tender, moist and had just the right amount of seasoning.

It was my first experience in Greece and right away I noticed a huge language barrier. Most of the conversation at the restaurant was based on pointing at the menu and making hand puppets, it was hilarious. Our original waiter, bless his soul. had to grab somebody else from the pub who understood English so they could take our order.

After dinner we mustered up the energy to take a walk to the Acropolis, so we could at least see it from the outside. It was dark and we were super tired but how could we go to Athens and not get a glimpse of it, it’s one of the most famous landmarks in the world. Plus, we needed to walk off all that food we just had. Just around the corner of the Plaka, which is a narrow cobblestone village near the city center, we could do nothing but stand and admire the Acropolis. There was something about the calm breeze and quiet streets that really made it special, even at night. Even though we couldn’t go inside, the positives were that there were no crowds to fight or the sun beating down on us. The negative was that we couldn’t go inside the Acropolis because it was closed for the day. After aimlessly walking the Plaka streets, we eventually headed home for the night.

Day 2 – Flying from Athens to Santorini

We got roughly three or four hours of sleep before we had to catch our flight to Santorini, Greece at 7am. Getting to the plane was a marathon though. ATH recently went through some renovations and let’s just say it’s a long walk, don’t be surprised if you’re winded when you finally get to the gate. It was cool that we got to go on the tarmac to board the plane. I’ve never been on the runway before and it brought a new perspective to boarding a flight, I felt like a rockstar!

It was a short fifty minute flight from Athens Greece to Santorini Greece. You couldn’t tell you were in paradise upon landing, it kind of looked like a baron desert. The airport is on the East side of the island and in the middle of nowhere, surrounded by sand, rocks and rubbish. We grabbed our luggage and scampered out of the small airport to hop on a bus for a few euros to the town of Fira.

Still tired from traveling the day before, we were dropped off a block away from Main Street. As we made our way up the long and steep hill of Mitropoleos, our checked bags pounded the cobblestone street as we went. Making it that much tougher of a climb to the top.

Fear not though as we were in for a delightful treat. I was awe-struck by the incredible view of the Santorini caldera, it’s astounding. The fresh ocean breeze coming of the Aaegan Sea, the smell of fresh buiscuits and coldcuts, it took my breathe away!

As we gazed in awe and stood there with out bags still in our hand, we didn’t but all notice our hotel was merely 15ft away. I was too busy being trigger happy with my camera as I kept firing away as many photos as I could.

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We sat and pondered about how we made it this far in the last two chaotic days, but we didn’t even notice our hotel, The Kavalari Hotel, was 20ft away from where we were standing. We couldn’t have picked a better location in Fira!! We were eager to check-in to our hotel and start navigating. Our check-in time was at 2pm and it was only around 9am but we were able to drop off our bags at the front desk for them to hold.

Pro Tip: Water is your friend, stay hydrated!

There was not much of an agenda for the day and we just wanted to take it easy before our hike to Oia later in the afternoon. We walked in and out of quite a few Santorini shops while taking a break to enjoy the beautiful views. A smoothie and an omelet sounded good, so we stopped shopping to eat. One of the best things about island life is that nobody is in a rush. It’s always “island time” and you really get a sense of that when you sit down at a local restaurant or cafe. Americans would classify the service as very slow, but it’s just the way the Greek culture operates. R-E-L-A-X-E

After getting lost in the narrow alleyways and peeking around every corner, it was time to officially check in to our first hotel of the trip. The check-in process was a breeze and before we knew it the hotel staff was carrying our luggage to our room. The sun really beats you up and as we learned, if you don’t drink a lot of fluid, you will get burnt out very fast. It didn’t help that we only had a little over a two hour slumber the night before.

I woke up from my nap refreshed and ready to go. I grabbed my camera and a few bottles of water and threw them in my backpack. Currently I am using a Sony A5000 mirrorless camera. It’s been a great camera to take pictures and also vlog on, I highly recommend it if your looking to get into vlogging without breaking the budget. Get it on Amazon here!

As we made our way up and down the numerous sets of stairs and down narrow village pathways, we could only stop what seemed liked every 10ft to take a photo or two. The hike was supposed to take roughly four hours, but we were way off the pace because of the heat and we made a few unexpected stops for more photos.

One of those stops was at Skaros Rock. Skaros Rock is one of the more famous locations in Santorini due to its large rock form shaped by the volcano blast dating back to 68,000 B.C. It has since been shaped by earthquakes and erosion. The best part about climbing to the top was looking back up at all the cave houses lined up on top of the caldera, such a site to see.

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As we continued our journey in and out of the shade, up and down roads and dirt paths, we started to run out of water and became hungry very quickly. The heat really started to take a toll on us and we found a corner convenient store just in time. Side-tracked, but now with some water and snacks we continued further to later realize that we weren’t going to make it to Oia for sunset. So, instead, we ended up at hotel Cilla. With an outside restaurant and bar to sit down at, we enjoy our first glass of  wine just before our first Santorini sunset! I would be lying if I didn’t say that taking the famous Fira to Oia hike is a terrible idea in the late afternoon, it’s just too hot. Don’t do it!

You’ve never experienced a sunset until you’ve seen a Santorini sunset, they are so beautiful. The sun looks so big and it feels so close, there is nothing like seeing it duck under the Aegean Sea. The sky is so vibrant, and the amount of colors are unlike anything I’ve ever seen anywhere else in the world. One sunset down and many more to go! We took a nice walk along the caldera edge to a bust stop that would take us back to Main Street. We didn’t waste any time getting to bed and recovering from the last few days. We were finally able to get a good night’s rest.