Santorini

Santorini was just as beautiful as I always imagined it to be. I went by way of London (roundtrip from Boston) and when the plane was landing in Santorini, I honestly started to tear up as I looked out the window. If you live in a major US city this will probably resonate with you - I really couldn’t believe just how blue and clear the water was. The whitewashed houses that lined the coast were exactly as I imagined them to be, punctuated by the bright blue domes and doors. It’s been over a month and I still think about Greece at least once a day. My friend and I went for 5 days but we honestly could have spent another 2 or 3 days on this one beautiful island.  

Here’s what we did:

Monday | October 2, 2023

  • Check in to Katikies Garden in Santorini

    This was the most amazing hotel. Stop searching for any other hotel in Santorini. You’ve found the one! The food here was amazing, the service was great, the staff was so so kind, and the rooms and amenities were incredible. The location is perfect because it’s removed from the crowds of Oia (I think most people either stay in Oia or Thira) but central to all the things you want to do and see in Santorini.

  • Sit poolside

    The pool has views of the caldera. It’s breathtaking, especially at sunset.

  • Dinner at the hotel

    There’s a “casual” side of the hotel’s Selene restaurant and a “fine dining” side. Both are obviously very different experiences but equally delicious!

Tuesday | October 3, 2023

  • Breakfast & Coffee at the hotel

    Breakfast was included in the price of our room - aka FREE if you’re doing GIRL MATH - and it was amazing. They bring you a basket of pastries before you even order your actual meal!! I almost didn’t come home.

  • Explore Fira (5 min walk from the hotel)

  • Spend the day by the pool until Chloe arrives

    My friend was meeting me in Santorini and arrived a day later than I did. Most people will tell you to go to Greece with your romantic partner but, trust me, going with your best friend is pretty amazing too.

  • 7:30 Dinner at Selene, the hotel restaurant

    Selene was amazing. Again, the staff was incredible. They were attentive and kind. The food was out of this world. Oh, also! They bring you blankets. If there’s a chill in the air the staff will magically appear with blankets to drape around your shoulders and keep you warm while you eat. They came in handy 3 hours later when we were just starting the dessert course. You gotta love Europe…

Wednesday | October 4, 2023

  • 8:30am pick up for boat cruise! 

  • 9:30-2:30pm Boat Cruise

    We chose Sunset Oia’s Small Group Morning Luxury Catamaran Cruise. It was an amazing experience. There are lots of yacht and sailing companies to choose from but I highly recommend Sunset Oia! 

  • Afternoon pool time

    Try the local rose while you lounge under a cabana!

  • 6:15 Dinner at Ammoudi Fish Tavern in Oia

    You’ll see this restaurant on Instagram and in blogs a lot - it’s totally worth the hype. GREAT view. Go at sunset. The food is amazing.

Thursday | October 5, 2023

  • Fira to Oia Hike

    I can’t stress this enough: I am not a hiker. You will never catch me putting on my hiking boots and walking through the woods for 3+ hours just for fun. And I don’t camp either. Don’t even get me started on camping. BUT, this hike is totally worth it. The views are breathtaking every step of the 3 hour hike. If you decide to do it, make sure to start early in the morning! We started around 7:45am and we timed it exactly right temperature-wise.

  • Lunch in Oia

    We wandered into Lotza and it was rustic and quaint and those words sound like veiled insults but they are not! I loved it. Get the eggplant!!

  • Swim at Ammoudi Bay

    Just beyond the Ammoudi Fish Tavern you’ll find a pathway that continues past all of the seaside restaurants and leads you to the most beautiful bay. along the water that eventually turns into a bit of a rock scramble. I’m probably being dramatic because, ya know, not a nature girly, but it’s a 7-10 minute walk/hike along the bay until you reach a “secret” cliff jumping location. If you’re not a risk taker like me, you can just jump in the water from a reasonable height as well. But either way, you’re in Santorini! The water is BRIGHT BLUE! Hide your stuff behind a rock, take as many items of clothing off as decently possible and jump! 

  • Walk back up to Oia (there are a LOT of stairs!) and get some gelato 

  • Spend the rest of the afternoon by the hotel pool

  • Dinner at Kaliya

    This is another spot with amazing views of the sunset over the sea. The hotel actually booked this dinner for us and requested a table with a view. We also may or may not have stopped for a second gelato of the day on the walk home…

Friday | October 6, 2023

  • Breakfast and coffee at the hotel

    I should note, I started every morning with a shot of espresso while watching the sunrise on the little rooftop of our hotel room. It’s totally worth the early wake-up.

  • Explore Fira some more

  • Afternoon pool time

    I’m still dreaming about the beef smashed burger from their “Tsibologima” (“snacking!”) menu. It was a great pre-flight meal. Pair with the local rose and no number of flight delays can kill your vibe. 

  • Late afternoon flight back to London

    Just a note for those traveling on a budget -  the flights over there were way cheaper by going through London as compared to flying direct to Athens (and then to Santorini). I flew into London, stayed a night then flew to Santorini. I did the same thing on the way home - flew Santorini to London, stayed the night, then flew London to Boston the next morning. Even with the London hotel costs, it was still cheaper.

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A Weekend in Boston