We had 4 full days in Santorini and we lovedddd every minute of it! If you can believe it, the island was even more stunning & romantic than we’d come to believe from our avid watching of Sisterhood of the Traveling Pants.
Unfortunately (fortunately), contrary to what the movie would lead you to believe, we did not have to ride a donkey with our luggage to our hotel room (though that would’ve been quite the story to tell!). Anyways, whether you’re honeymooning or just want a relaxing (gorgeous) getaway trip, 10/10 would recommend Santorini!
Top 10 things to do in Santorini
#1 – Admire the incredible architecture in Oia
This town is straight out of a fairytale (and the most famous one you’ve seen on like everyone’s insta-posts I’m sure). Make sure to take your time and just wander (in the daylight) around Oia!
#2 – Watch a sunset (warning: unpopular opinion ahead)
We’d heard Oia was home of the most beautiful sunset in the world. The first night we watched from our balcony in Firastefani, and the second night we watched from a hillside bar in Oia. Shh, don’t tell… but we found the Firastefani sunset to be just as stunning, and a 100x better experience!
While the Oia sunset was stunning, don’t get us wrong, the experience was pretty stressful. Between having to find a place to sit down an hour before to get a view, having that view blocked by a million people and their selfie sticks, and then not being able to move when the sunset ends to get around Oia… it just wasn’t the magical moment we’d hoped for.
Vs. 
Reality
Whereas Firastefani was much more calm and we could grab some wine and watch the sunset uninterrupted, taking in the moment and not worrying about logistics. Now THAT is magical.
Pro tip if you do decide to do the sunset in Oia venture: stay after the sun disappears! This is when the crowd leaves and you won’t be able to walk anywhere anyways, and the sky is arguably even more gorgeous!
#3 – Explore the shops in Fira
Fira is the capitol of Santorini & has tons of shops and restaurants! It also has the best night life on the island and is where you take the ferries to/from the island.
#4 – Hike from Oia to Fira
The 2.5 hour hike through the caldera cliff & villages of Santorini is amazing! We were short on time (and didn’t have proper footwear) so we took the bus from Oia to Imerovigli and walked from there to Fira. The part we did was amazing and only covered the last 30 min of the hike, so we definitely want to do the full thing when we go back!
#5 – Eat a gyro (or 20)
Still dream about these. We got them at least twice a day, without fail. We pretty much became BFFs with the restaurant owners at Why Not! Souvlaki in Firastefani and it was pretty heartbreaking to have to say goodbye. A lot of the restaurants can be pretty pricey, so honestly since we’re not big fancy foodies, gyros were the most delicious, quick & inexpensive way we could eat in Santorini.
#6 – Take an Ouzo shot
Ouzo is Greece’s national drink, so naturally you have to try it. If you dig licorice, it’ll probs be your jam. If not, plug your nose and check it off your bucket list like we did!
#7 – Soak up the sun
Santorini is a gorgeous place to just relax for a few days, lay out and soak up the sun!
#8 – Get up close & personal with the donkeys
I believe you can ride the donkeys up the steps in Oia, but honestly you’ll see them just walking through Fira when you’re shopping. Definitely felt like a very Greek thing to experience lol.
#9 – Take a ferry to another Greek Island
The ferry to Mykonos was an experience in and of itself! It was amazing to see all the islands from the vantage of a boat, and the ride was super enjoyable. We recommend splurging on business class, which gets you access to the outside deck of the ship.
#10 – Enjoy your company!
If you’re traveling with a partner, soak it in! The island is a super romantic place, and whatever you choose to do with your time there is going to make for incredible memories together.
Quick tips
- Go in September – it’s still stunning weather without being too too hot, and the peak summer tourist season is dying down (warning: it’ll still be pretty dang busy, especially when cruise ships are in town!)
- Splurge on the hotel with a view & pool, especially if you’re planning more chill time & less excursions.
- Stay in Firastefani! We absolutely loved this area for so many reasons. It is the perfect mix of quiet and busy vibes (not quite as secluded/quiet as Imerovigli but not as busy as Fira), much more affordable than Oia, walking distance to Fira, gorgeoussss spot for sunsets and tons of little restaurants/shops to grab wine/etc.!
- We stayed at Villas Illias in the rooftop suite and I kid you not it was like torture having to leave that place!
Overall, Santorini is pretty much as picturesque and romantic as it gets. We can’t wait for the chance to visit again!
Happy traveling!
Kylie & Scott
(Want to know more? Comment below! And make sure to follow along on Instagram @LoveHardTravelOften)
Santorini is my dream destination, I will go there very soon.
Thanks for your awesome travel guide.
Photos are really mind-blowing.
We are so happy to hear that! Thank you so much <3