The Land of The Influencer: Santorini, Greece

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Originally written September 13th, 2019.

We arrived in Santorini around 10am, and had arranged for a cab to meet us via our Airbnb host. The cab whisked us off to Oia, about a 30-minute drive from the airport. When we arrived in Oia, it was easy to see it was full of tourists. We fought our way through the crowds to leave our bags with our Airbnb host until our house was ready. One of the workers who helped us with our bags dropped us off at Pelekanos for lunch. We enjoyed the view of Santorini from the top, and thought the food was pretty good, even if I'm sure the "guide" probably got a nice tip from the restaurant for taking us there! After lunch, we found a spot for a cocktail as our house was still not ready. The spot was on my list as a great cocktail bar, but it was just a glorified coffee shop with alcohol. It was great to pass the time but didn't have much of a view or anything special to drink/eat. Once we finally checked in to our house we were blown away! We had our own rooftop patio, hot tub, and two separate bedrooms for both of us couples.


We all decided we did not want to fight the tourists and crowds any longer and immediately changed into our suits to lounge around our house. I picked 1800/Floga for dinner based on my list and the reviews it had. The view was insane and since we choose to try and fit dinner in before sunset we were the only ones in the whole place for most of our meal. The service was good, but they all lacked English vocabulary which is the first place we'd really had trouble. We all thought our food was good but not great, but we enjoyed the bottle of wine we ordered for the table and the view.


After dinner Drew and I went to find the best view of the sunset with the least amount of tourists and struggled. We ended up on the other side of the island to catch a quick peek, and while we throughly enjoyed it - we definitely feel like we've seen our fair share of impressive sunsets. Basically, sunsets aren't going to make or break a trip or city for us.

We were told by our host we'd get to see a great sunrise from our house, so we set our alarms to wake up on time and finally hit the hay. The sunrise from our house was great and I'm happy we woke up early enough to see it. Drew and I also ventured down around the island after the sunrise and were excited to find it mostly empty. That is except for the insane amount of photographers following around couples and Instagramers trying to get the perfect shots sans tourists. It was SO fun to see them all in action and we followed a few around to see where they would go (a bit unintentionally). Our house was located right below the "famed" spot in Santorini to grab a picture with the "famous" blue domes. We were able to finally get down to this spot without a line of 50 (seriously) Asian selfie stick holders only because it was still just 7:45am. It was a cool view, but no cooler than our hotels view.


We took the rest of the day to lounge around our house, stopping to head out for lunch at Lotza. I had an incredible Mediterranean burger - probably my best meal on the trip and Drew had garlic mussels he also very much enjoyed. The view from the spot helped!

Before dinner, I put on the two most recent pieces I bought locally for our trip in hopes of getting some cute photos both just with the clothes (#instagramer) and because I had hated just about every other photo taken of me in Santorini up until that point. Note to self - stop wearing dresses when it’s windy. I am very happy with the photos I got - thanks Drew!


We spent our evening walking down the island in the opposite direction that we had the days before. Eventually landing on a great spot to catch the last of the sunset and to have dinner outside. We all felt like our dinner at Flora was really good and we were surprised we were able to find a table.

Eating in Santorini is hard (much like Rome) because you pass so many spots on the street it’s hard to know what is and isn't good. I think we had a little bit easier of a time deciding in Santorini, but it was still a little annoying. Everyone serves the same food and has the same view sooo at some point you just have to make a decision!

Our last morning was spent grabbing a few more photos and enjoying coffee with a view. We packed up our bags and had one last lunch in town before hopping in a cab to a winery near the port. I had the idea because I felt like we'd be able to kill some time at a winery as check out was at 11 and our boat to Crete was not until 5:45pm. Best idea I've had in a while. When we arrive at Santo Wines we were immediately whisked away to put all of our bags away for safekeeping which was COMPLETELY unexpected. I anticipated lugging them around all afternoon. Then we sat down and decided to do the 16 glass wine tasting and split it between the four of us. We had 3 hours to kill after all!

The wines of Santorini are very different but it was awesome to taste a bunch of different grape variations. I would've loved to hear more about the wines and harvest etc. but drinking them was fun. The view didn't hurt either!!


Then we grabbed a taxi down to the port and proceeded to walk into one of the biggest shit shows I've ever been apart of. I felt like I was genuinely in a sea of chaos at the Santorini Port. There were no signs or directions for check in, and our email about our boat just casually mentioned needing printed tickets. We eventually worked our way into what seemed like the gates only to notice everyone had paper tickets but us. As a boat arrived (not ours, and thankfully it was going to another Island so we knew for sure it wasn't us), we all almost got swept up into the pandemonium of trying to get 200+ people onto one boat in 5 minutes. Literally 5 minutes is all they give for all of these people to make it on the ship. I eventually asked someone around us where they got tickets and Drew and I managed to find the office and get our tickets.

I spent a decent amount of time fighting a little old Greek lady to let me use the bathroom (I'm tired - ask me for the story another time) and then before I knew it I was us being whisked away on our giant boat like herded cattle being sent to slaughter. If you had fallen trying to get on the ship I think you would've been trampled and left behind!! THANKFULLY Drew and I spent the extra $5 a piece to upgrade us to VIP and all of our first world problems melted away as we were escorted to our window front VIP table.

More on our boat trip and our fantastic Heraklion Airbnb tomorow!! Xoxo.


Haley G.

Haley has always loved reviewing locations and being in the know about the best neighborhoods, restaurants, and events in Cleveland. This passion fuels each guide and article she creates for The Cleveland Bucket List. She hopes you enjoy her stories and guides and get inspired to create an adventure of your own!

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