48 Hours in Santorini

Much like Athens was on Zack’s bucket list, visiting the Greek Islands was on mine. I always told him when we go back to Athens, we are visiting the islands too.

Unfortunately Zack couldn’t come due to work, BUT my mom and I headed off on an adventure of our own: a week in the Greek Islands!

And up first: Santorini.


We arrived to Santorini around 11am, and our airbnb host picked us up at the airport. We stayed in Fira, the island’s capital and a cute little town that’s definitely worth exploring. It’s only 10 minutes from the airport, and it’s where the cruise ships come in as well. 

Our airbnb was a super cute house and our hosts were incredibly sweet. And since we were visiting in the off season, it was under $100/night. 

After freshening up, we headed out to explore Fira for the day. 

Up first, we walked down (and back up) the steps to the Old Port. All 600 of them (and that’s one way!). Our legs were burning. And I’d recommend not wearing sandals like I did. I survived but the path and steps are cobblestone – so very uneven. And you have to dodge a LOT of donkey poop. 

There’s honestly not much at the bottom – it’s where everyone from the cruise ships come in, but you do get some nice views of Fira. And seeing all the donkeys was pretty cute.

Speaking of donkeys – if walking down and up 600+ steps isn’t your vibe, you can pay to ride a donkey OR there’s a cable car. We just decided to do it the hard way. 

Our legs needed a break so we grabbed a drink at a little bar called the Art Cafe. It was in a quieter area of Fira, and we ended up having the whole place to ourselves. And what a view.

As if we hadn’t gotten our steps in, we decided to just wander aimlessly through the town – all the houses, churches, and squares were just so dreamy. And the views were stunning in every direction. 

We decided to grab a spot for sunset. Not only was visiting Santorini on my bucket list. but specifically seeing the sunset in Santorini…and that goes for just about everyone else that visits, so it’s a good idea to find a place early and hunker down. I will say, we were lucky that there were only 2 cruise ships docked (because October), so it wasn’t as crowded as it is during the high season where there can be as many as FIVE! I can’t imagine how crowded it must be! 

We found the perfect place to sit and watch the sunset. The pictures don’t even do it justice! 

We had reservations for dinner at Argo – which is also a great place to watch the sunset if you can get a seat on their rooftop balcony. The food was excellent – my mom and I shared an appetizer (bread with various tapenades), a salad (the honey dressing was the star), and a ravioli with walnuts and honey which was so rich and delicious.

The wind had really picked up, and we were actually freezing, so we hurried back to our airbnb for the evening. Actually – that’s a lie. We grabbed some gelato first…even though we were freezing. Because gelato is always a good idea. 

DAY 2 

We headed out around 9am and grabbed a quick tea and pastry from a nearby coffee shop before doing the hike from Fira to Oia, where we planned to spend the day. 

It’s about 10k (6.5 miles) one way and is a mix of paved roads and dirt trails. There are a few steep parts, but overall it’s pretty easy. It’s easier (and recommended) to go from Fira to Oia and take a taxi or bus back. Definitely wear sneakers, sunscreen, a hat, and bring a water bottle. If you’re going in the summer, head out EARLY to beat the heat. 

The walk will take at least 2.5-3 hours and hugs the caldera so you’ll have incredible ocean views. From Fira, you’ll pass through Firostefani and Imerovigli before ending in Oia. You’ll also pass by Skaros Rock which you can walk out to as well. This will probably add an extra hour. We started to head out to the rock but ended up turning back because the wind was so intense! 

I found this website really helpful if you want even more info about the hike!

We made it to Oia around 12:30 and decided it was time for a pre-lunch cocktail. We stopped at Apsithia and sipped on mojitos while soaking in the view. Then we headed over to Pelekanos for lunch. This rooftop restaurant is easy to miss, but definitely worth finding. The food and views were top notch. My mom and I shared ntomatokeftedes, a must try Santorini specialty – tomato fritters made with local tomatoes – and they were SO good. For our entree, we ordered a salmon linguini with a creamy saucy and it was amazing too. 

Any picture you’ve seen of Santorini is probably Oia. It’s famous for its sunsets and dreamy cave homes, and there’s just so much to explore. Which is how we spent the rest of our day. 

The best plan is to really have no plan and just kind of wander aimlessly – there isn’t a bad view. From the iconic blue domes and bells, to the famous Pink Kastro Oia Houses (which are more orange than pink, but make for a great photo op), and more. We also walked down to Amoudi Bay (another 300+ steps…one way). Plus there’s so many cute shops to check out.

And of course – you have to stay for sunset. Oia Castle is one of the top places to watch the sunset, so get there early and expect crowds. We got there over an hour early and had a front row seat on the castle wall. Even in October, it filled up quickly. People were lining the streets and sitting on balconies to see the famous sunset. 

And it was so beautiful. Not just the sunset itself, but how it reflected on the white-washed buildings. Just magical. 

And did I mention cold and windy? But I’ll take that over the super crowded high season. 

We took a bus back to Fira, grabbed gelato for dinner (it’s vacation – we make the rules!), and called it a day. 


For our final morning in Santorini, we grabbed breakfast at Coffee Shop Vales then took another casual stroll through Fira before heading to the airport for our flight to Milos…which is a whole other story that I’ll be sharing in my next blog.


Santorini was everything I hoped and more, and totally lived up to the hype in my opinion. Based on my visit, here’s a few thoughts/tips/suggestions:

• Visiting in off season is great for lower prices and fewer crowds, BUT it was actually pretty chilly and very windy. I think it was actually abnormally windy during our visit but definitely something to keep in mind. Although I’d opt for the cooler weather over the summer crowds.  
• You’ll definitely be able to find budget friendly options if you look for them, but it is an island so expect higher prices. 
• From Athens, you can fly or take a ferry to Santorini. We chose to fly because there were plenty of short and inexpensive flights to choose from. The ferry schedule was very limited in October (and through the winter), so that played a big part in our decision as well. (Although I will say the wind can definitely affect flights – I’ll be sharing that story in my next blog but spoiler alert: we experienced major delays because of it!)

That wraps up our quick trip to Santorini! Be sure to check out the links below for all the blogs and videos from our fall Europe trip. 

– Courtney


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