Santorini, Greece.

Join me as I take you through our time in Santorini, Greece. What to see, what to do, & what to eat. Enjoy!

We took a quick flight from Athens to Santorini, with a few islands to admire from above along the way. Santorini is a place I have dreamed of going since high school after seeing Giada DeLaurentiis travel to Oia on her food network series Giada Travels. Just one glimpse of her swimming across the famous infinity pool overlooking the caldera had me sold. If you are wondering about my undying devotion to all things Giada, you can read more about my favorite things and get a little more  “Claire-ity” on Claire.

Day No. 1

Upon arriving in Santorini we were welcomed at the airport by our private motor transport which took us across the island to our hotel in Oia. We were greeted near the hotel by awaiting hotel staff that led us down the winding paths of Oia while carrying our luggage atop their heads. From the moment we arrived my breath was taken away. It could have been from all the stairs that we had to take, or the utter beauty of a place I have dreamt of for years. Either way I will just go with the beauty of my surroundings to pad my cardio ego.

Once we made it to our location The Esperas, I was in love. The quaint hotel packed a huge punch with an incredible view. Fittingly our room was inside a little cave, and absolutely lovely. We quickly changed into our bathing suits to relax at the pool and soak in the view of the Caldera.

We spent the afternoon by the pool with lunch and refreshing cocktails that were a nice “welcome to Oia”. One of these drinks was so tasty and memorable it inspired me to recreate a cocktail from our stay. I named it the Grecian Cucumber Mint Cocktail, careful, it may knock your socks off.

After maxin’ out, relaxin’ out, and bein’ all cool. We headed back to our room to shower and get ready for our first date night in Santorini. When doing my usual pre trip research that I detailed in “How to Plan Your Vacation”, I came across Ambrosia. We wanted one evening with a romantic dinner setting that had a sunset view and Ambrosia fit the bill. We enjoyed the view and food, and it served as a very nice introduction to the beauty of Oia.

After dinner per the advice of a local when we inquired about the best gelato in Oia, we were directed to Lolita, and straight to Lolita we went. We made our way through the alleys of Oia to an adorable little spot that exceeded my expectations from the start. From the logo, to the color scheme, to the cute outdoor seating I thought I was in heaven and I had not even made it inside yet. Thus far the hardest decision I had to make on this trip was which flavors would I choose. Being a creature of habit I went with Pistachio and Cheesecake, the two complimented each other so well and I was in H-E-A-V-E-N!

After stuffing ourselves silly with gelato, we stopped into the most unexpected find. We noticed some books along the main pathway in Oia with stairs leading down to a little sign reading Atlantis Books.

I cannot say enough about this quaint little bookstore. They had quite a collection including first editions of classics such as George Orwell’s 1984, and Ernest Hemingway’s Old Man and the Sea which were listed for as much as 5,500 euros. The store’s owner sat behind the counter and was so kind, not to mention his little pup that relaxed beside him and welcomed all belly rubs. We picked up quite a few books, and even made away with a children’s book about the island of Santorini for our future littles. At check out we were delighted when the owner asked if we would like each book hand stamped, this was something we appreciated and made this experience even more charming. After we made our purchases and said our final goodbyes to the store mascot, we made our way back to our sweet cave for the night.

Day No 2.

We started our second day with an early breakfast that was delivered down to our room. One of the great things about The Esperas is that each day you fill out a sheet that has an assortment of breakfast items and it is delivered straight to you the following morning, if I could only bring this custom back home I would be set. You can choose to have it inside, or setup on your balcony overlooking the sea, which makes the stay all that much more special.

The reason we had such an early morning on this particular day was because we had a photoshoot with Flytographer scheduled. I talked more about our previous experiences with Flytographer in my recent post here. I would recommend using them if you are planning a special trip with your family or loved one to document memories to have for a lifetime.

After our shoot, we took time to explore around Oia. Our first stop was Oia Castle, where we took in the views of the caldera and soaked it all in while looking out the old roofless, doorless, windowless castle.

From Oia Castle we decided to conquer the stairs down to Amoudi Bay. Be forewarned, they are slightly slippery from decades of soles walking the marble pieces that lay throughout, I would recommend a stable pair of shoes for this venture.

Once we made it down to Amoudi bay, we soaked up the sight of the crystal blue water and made our way to Katina’s. At Katina’s we enjoyed some fresh octopus and fish a stone’s throw from the beautiful bay. Being fully transparent, unfortunately one portion of our lunch at Katina’s was not exactly as stellar as anticipated but they handled our concern beyond our expectations and were very accommodating once we shared our concern with them.

After lunch my husband was feeling bold and decided he wanted to cliff jump into Amoudi Bay, so cliff jumping we went. Needless to say, I stayed behind the lens for photos and snapped away.

Once he had cliff jumping checked off the list we decided we were not going to use the sweet little donkeys waiting to take you up the 300 or so steps, but that we would tackle them ourselves. With that being said, this was a task after a big lunch and the heat. Thankfully we survived because I am typing this post, but it was touch and go there for a minute.

After we made it to the top of the path, we decided to celebrate our recent victory of stair climbing and went on the hunt for coffee. We made our way all the way down to Passagio for a little afternoon refresher and I must say, the coffee and atmosphere was absolutely lovely. Our next planned destination for the day was Akrotiri, and Passagio happened to be right next to the pickup point.

Akrotiri is an ancient archeological site thought to be Atlantis. Current estimates date Akrotiri back to 5000 years BC and was then covered by lava flow from a volcanic eruption around 1627 BC. It contained such advanced architecture for those times with not only drainage, but toilets, pottery, art work, paved streets, and a town square. It will stop you in your tracks to think of the thinking and planning that was done so so long ago. If you go all that way, please take the time and visit.

After we had our history lesson checked off the list we made our way back into Oia and grabbed dinner at Z’s Bar & Burger. Of course I opted for my frequent favorite, pizza. It was just what we needed after a day of exploring. The restaurant is in a perfect location if you like to people watch as it sits along a main pathway leading in and out of Oia via bus or automobile. While we were there the sweetest local pups visited us for our meal and left a sweet lasting impression. Another benefit to the location of Z’s Bar & Burger is that it happens to be right by Lolita, the best gelato in all of Santorini. So needless to say, we finished the night with more gelato and a stroll.

Day No. 3

We started our third day with another early morning to explore and photograph the narrow pathways of Oia. It was so peaceful and nice to have such an amazing place all to ourselves while everyone else was tucked away catching their zzz’s. We walked around to take early morning photos and once we were done we headed back to our hotel for breakfast that was served outside our room on our private balcony, overlooking the sea.

If you do not have a “pinch me, is this real life” moment then good for you, because you must come here at least once a month. I feel no matter how many times I visit Santorini I will be in a constant state of “is this real life?”. After we finished breakfast we headed to Vitrin Cafe Creperie for a latte on their patio, they have not only fantastic views but great lattes as well.

The rest of the morning we spent shopping throughout the island to pick up a few local items and then went over to Kissing Fish for a long-awaited fish pedicure.

Once we had our feet kissed all over by little fish we went for lunch at Nikos Place. This was a great lunch with authentic Greek food that hit the spot. The portions are large so if you are looking for a light lunch, you could consider sharing something.

After lunch we went back to our hotel to get changed and freshened up for our afternoon sail on the water. We booked an afternoon on the water with Caldera Yachting, which included a tour of many key beaches and characteristics of the island, along with an awesome display of the sunset. You sail around most of the island, with a few stops along the way with options to swim or just marvel in the beauty of your surroundings.

As we sailed around the island they prepared an excellent fresh cooked dinner aboard the boat. After dinner was the real beauty, the sunset. Watching the sun set from the water on our last evening in Santorini was the best farewell to this amazing segment of our tour de Greece and I am so happy we ended our trip to Santorini this way. I cannot say enough great things about the boat staff, the hospitality and attention to detail in such a relaxed environment was more than we could have asked for.

Once we made it back to Oia after sunset you guessed it, we went for one last farewell gelato stop at Lolita. If I could snap my fingers and be back there with that oh so delicious cheesecake and pistachio gelato I would be there every night without question.

I hope you enjoyed exploring Santorini with me. It was such a magical experience and I am so blessed to have been able to explore such a magical place with my best friend.

On to the next stop, Mykonos.

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Where to Stay:

Esperas Santorini

Places to go:

Amoudi Bay

Atlantis Books

Places to see:

Oia Castle

Stairs to Amoudi Bay

Blue Domes of Santorini

Windmills

Caldera

Places to Eat:

Ambrosia

Lolita Gelato

Passagio Coffee

Z’s Bar & Burger

Nikos Place

Vitrin Cafe Creperie

Activities to do:

Flytographer Photoshoot

Cliff Jumping in Amoudi Bay

Kissing Fish Pedicure

Akrotiri Museum

Island Cruise/Sunset Cruise

Winery Tour

Things to get:

Local Books

Jewelry

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XO

Claire B.