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Exploring Santorini

Updated: May 8, 2023

Day 1

Since we arrived at our hotel after midnight, we didn’t get a good sense of the island until the next morning when we woke up. Upon opening the windows, we were greeted by a sweeping view of the water and adjacent island. We headed down to the lobby area for breakfast and to finalize our check-in before heading out for the day.

Oia, Santorini, Greece
Oia, Santorini, Greece

We started off by hiking up to the Castle of Oia to take in the sights of the surrounding area. Seeing all of the buildings carved into the cliffside was very cool and the area had 360 degree views out over the collapsed caldera that made up the bay and the surrounding islands.

Oia Greece from Above
Oia from Above

From there, we walked back towards the main part of town, down a set of narrow alleyways, and eventually ended up on the main “street” of Oia where Mrs. ATX Jetsetter did a little bit of shopping.

Around 11:30 we made our way back to our villa as we had booked some in-room massages for noon. Given the fact that we wanted to have the view out over the water while having our massages, the doors to the villa were open which was slightly weird as random people would just walk by on the path outside. After our massage, we headed down the hill for a late lunch in Ammoudi Bay. The path was more like a long set of winding stairs but since we were going down it was not a problem. For those who do not want to walk they have donkeys for hire as well as a road between the dock and the post office in Oia that one can access via taxi or private car.

Once down at the waterfront we made our way to Katina Fish Tavern, which was recommended by the helpful front desk staff at the hotel. We were seated at a table right at the water's edge and looked through the extensive menu of fresh fish. We started off with a couple of beers and when it came time to order, our waiter was extremely helpful and even took us inside to pick out the exact fish that we wanted.

After placing our fish order, we started with a delicious Greek salad and a freshly cooked large shrimp. Afterwards, our fish appeared and it was perfectly cooked. One was Sea Bass and I can't remember what the other one was at this point, but they were both delicious. While enjoying our meal, we struck up a conversation with the couple next to us who were from Chicago and also on their honeymoon. The manager came by around this point and, after overhearing our conversation, brought us both complimentary baklava and ice cream for dessert.

Full from lunch, we decided to walk it off on the trail surrounding the bay. We walked out to the point which had a great view back towards the main waterfront of Oia before making the climb back up the steps to our villa. It was much easier going down than going up.

Back at our room, we sat on the terrace and read while watching the ships go through the bay en-route to another one of the Greek Isles.

Ferry in Ammoudi Bay
Ferry in Ammoudi Bay

Relaxed and recharged, we headed back into the main town square and checked out the interior of the town church before stopping for a quick snack and a drink at one of the local restaurants.

After our snack, we raced back to our villa to catch the sunset, which many tourists on the island travel to Oia each day to see. Many of them cram onto the pathways around the old ruins so it was nice to be able to watch it from the comfort of our terrace. While I know my photos won’t do the real thing justice, it was a gorgeous sunset.

After sunset, we walked over to Ambrosia Restaurant for our dinner reservations which we had arranged through our hotel. We were welcomed by the friendly staff for our 9:00p reservation which was coordinated by the hotel and led to a table right at the edge of the open-air patio which had more great views out over Oia. I really enjoyed the light of all the pools reflecting off of the buildings.

I remembered to take pictures of a couple of the dishes but didn’t think to get any of the menu or even note what we had. All I do know is that everything was delicious and by 10:30p we were back in our room sleepy and full. We called it a night as we had another big day coming up exploring Fira, and hiking from Fira back to Oia.

Day 2

After an extremely restful night's sleep, we awoke to another picture perfect day in Santorini and headed down to the lobby once again for breakfast.

Morning in Oia, Santorini, Greece
Morning in Oia

Fueled up for the day, we made our way to the town square to board the bus to Fira. The bus tickets were ridiculously cheap, I believe they were less than a Euro each, so I was pleasantly surprised when a nice motorcoach pulled up for the 30-minute drive around the island.

Upon arrival in Fira, we had no real plans and just followed a group of people up the hill in the general direction of the waterfront. There were a lot of cruise ships in port that day and the town was beginning to get overrun with people as they made their way onshore. Due to the narrow streets, we decided grabbing lunch sooner would be better before everything was too crowded to get a table. We found a restaurant high above the water called Zafora which had a beautiful view of the ships in the bay below.

We started with a round of drinks while we perused the menu, which is below.

We both decided to have some gyros before heading out.

After lunch, the crowds in Fira were really getting bad with all of the cruise passengers so we decided to start on our hike. Mrs. ATX Jetsetter had read about a roughly 7-8 mile trail that led from Thira to Oia along the cliffside and was hell bent on hiking the whole thing. Thankfully the weather was perfect and the views weren't too bad either.

Panorama leaving Fira
Panorama leaving Fira

Not far outside of the main part of town, we came across the famous Three Bells of Fira, officially known as The Catholic Church of the Dormition, with the three distinctive arches accompanied by a blue dome. This view is on almost every image of Santorini and, while beautiful, you basically were standing in a dirty gravel car park to get this photo.

Three Bells of Fira
Famous Photo, taken from a car park

After leaving the church, the towns got smaller and further between before eventually giving way to a more rural landscape. In some areas it was hard to tell whether or not you were still on the trail but we kept walking in the general direction we were supposed to and found the trail each time.

At the highest point of our hike, we came across a small church tucked into a grove of trees, where a few other hikers were resting in the shade.

Church on the hike from Fira to Oia
Church along the trail

From the church, we headed down the hill towards Oia. Along this section, the trail is mostly well marked though there is a roughly 500m section where you are walking along the shoulder of the road. Some entrepreneurial minded folks set up a concessions cart of sorts so we stopped here for a drink and a snack before continuing on.

The last couple of miles into Oia were mostly downhill and had views of both the water and the adjacent countryside. The closer we got into town, the more traffic we encountered and eventually we found ourselves back on the main street through Oia.

After a fun but long hike, we rewarded ourselves with a snack at one of the cafes in town. From there, we headed back to our room to wash up for dinner. On the way back, I grabbed a couple of local beers that came highly recommended from someone on FlyerTalk and stashed them in the fridge for later.

After washing all of the trail dust off, we caught another beautiful sunset before making our way over to Aspa for dinner. This restaurant came very highly recommended by the owner/manager of Katina Fish Market. He warned us that it was a little off the beaten path, in a nearby hotel that had just reopened. It took us a while to find the restaurant, I even stopped in some art gallery and asked the proprietor for directions, but ultimately, we made it in time for our reservation.

We were seated as the last few rays of sun were setting and for the next couple of hours wined and dined to our hearts content. We started off with a round of cocktails.

This was followed with appetizers, I had the scallops, which we accompanied with some champagne.

I followed that up with some delicious sea bass and then dessert.

They also offered us some sort of local liquor which I remember being extremely sweet.

ASPA Restaurant Santorini Dessert Liquor
ASPA Complimentary Dessert Liquor

Stuffed full and exhausted from our long day, we headed back to the hotel to pack and get some sleep as we had an early morning flight to Athens the next day.

All in all, we really enjoyed our time in Santorini. Out of all of the destinations on this trip it was the one place we wished we had spent a few extra days. We absolutely plan to return to the Greek Isles soon!


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