Santorini in a Weekend

Ok, Santorini was ACTUALLY where we meant to go all along (see Mykonos blog post). This is where I heard I could see the beautiful white buildings with the blue roofs along the cliffs to the gorgeous ocean. This is what I always pictured as “Greece” as a naive American, but oh well, I wanted to indulge! Let me say, Santorini did not let me down. Everything about being here was breathtaking & magical. It’s one of those places where you think, “even if I lived here, I don’t think I could ever get used to this”.

Where to stay

If you really want to see the authentic buildings you always dreamt of, you will have to head to Oia. This is where you will find those beautiful buildings & jaw-dropping cliffs. It really is unbelievable. The town is picture-perfect with cobblestone alleyways that wind through the perfectly white buildings. This is where you want to stay.

As for hotels, the hotel we stayed at in Santorini was actually my favorite hotel out of all of Greece & Italy. We walked in & our jaws immediately dropped & my husband’s first words there were “WOW. Great job babe…” So if you’re looking for that reaction, head to Sofia Boutique Hotel. While you may be shocked at the price (we were, too), we decided to splurge a little because this was the place we really wanted to remember. And we always will. With our private plunge pool, cave-like room, beautiful bathroom, chic bar & lounge, there was no topping this. 10/10!

Where to eat

I actually don’t have a specific restaurant to give you on this one because my recommendation is to actually try out a bunch of places throughout town. Try not to go too crazy at just one place & save your appetite as you make your way down the cliffside. Always go for the restaurants with a view out over the cliff to make the most of your experience! Try a little bit of Greek food here & there & you will be thoroughly satisfied.

What to do

My #1 recommendation that you should take away from this is to see the sunset over Oia. This was quite possibly the prettiest view I have ever had in my life. One that I actually seem to have a snapshot of in my mind that I keep picturing as I write this. And guess what? The best view you can get of it is at the Sofia Boutique Hotel. I swear to you – they are not paying me to write this. It really just is that amazing. Picture this – watching the sunset in your private pool/on your pool bed sitting in silence because of how awestruck you are. Perfection.

I realize that there are many more hours in the day than just the sunset, so here are some more recommendations. Spend a full day just exploring Oia. There are so many shops & restaurants to wander into & so many picture opportunities around literally every corner. Make your way to the famous blue-roofed churches. If you take the main walkway along the cliffside all the way to the end, you will even find one you can stand on to take an Insta-worthy pic!

On your other day in Santorini, absolutely take a catamaran tour. We are suckers for boats & islands. This may be because of our incredible luck (we somehow got a private tour for the price of a regular one because no one else booked it), but I really think you’ll love it, too! We did a tour of all of the beaches on the island – the red, black & white beach, along with many others. We also got to swim into the hot springs where we wrote our names in the mud on the rocks & enjoyed floating around. This is always one of our favorite parts about trips, & this boat tour did not disappoint.

Whatever you do, I promise you will LOVE Santorini, & it’s totally possible in a weekend!

Random tips

  • If you aren’t staying in the city center of Oia (like if you stay at the hotel we stayed at), take the walk into the city. It was about 20 minutes for us & it was a great walk. Even stopped to pet a cow that was just hanging out! It’s nice to just take everything in, especially when you are going from car to bus to boat to plane.
  • Once in Oia, walk everywhere, even the alleyways. There are so many hidden shops where you can find beautiful, locally crafted trinkets to take home.
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