Three Perfect Nights in Santorini

We flew into Santorini from Athens and used a really small airline to save money. Our flight was only about fifty minutes and was a direct flight. Santorini has a small airport and has only one baggage claim (note that for when you are flying during a busy time of the day). We took a night flight and was the only plane that was landing at that time. Since we flew in so late, we didn’t arrange prior transportation and definitely should have. The taxi’s are so expensive because airport is located on the far side of the island. We paid forty euros for a taxi that was fifteen minutes from our first hotel, which was located in Perissa.

Oia Night

Perissa is one of the less touristy parts of town. It is near the airport and also near Red Beach. We stayed in a small hotel due to the fact that we weren’t going to arrive until ten P.M. Our taxi driver was sweet and quiet. The ride took us approximately twenty minutes. We enjoyed seeing the brightly lit Oil hilltop as we drove. When we arrived, our boutique hotel was tucked back off of the main road. Our room was small, with just barely enough room for the twin sized bed and no air conditioning. It wasn’t elaborate by any means, but perfect for the twenty dollars we spent and a nights sleep. That night we walked across the street and went to a tiny tropical themed bar that was jam packed with people due to the World Cup Finals. We ordered fancy drinks and sat amongst both locals and tourists from all over the globe and enjoyed the yelling and cheering for the soccer teams. After we went back to our hostel and went right to sleep.

We were excited and Eager to begin our first full day in Santorini. I have been dreaming of Santorini since I was a small girl. We ate a homemade breakfast from the owners of our hostel and headed to a fancier hotel in the town of Monolithos. Monolithos is located smack dab in the middle of the island on the East, and is still far out from the most known town of Oia. The hotel we stayed in Memories Beach Hotel was absolutely amazing. This hotel was one of our “splurges” throughout the trip. We wanted to stay somewhere really nice in Santorini. Our suite was beautiful and completely remodeled. The staff at the hotel were beyond amazing, and did everything to ensure we had all that we needed. The hotel itself is right across the street from the beach, we could see it from our window. Downstairs was a huge outdoor pool with an outdoor and indoor bar. It was sort of stuck back and secluded from everything else- very peaceful and quiet!


That day, we spent a lot of time at the pool. We order drinks poolside and tanned in the Santorini heat. That night, we ate dinner at the restaurant next door. It was a small, local restaurant ran by a cute old man. I ordered a pasta and Jack ordered a homemade pizza. The seating was an outdoor patio that overlooked the ocean. We were the only ones at the restaurant so we had undivided attention of the staff, and a nice relaxing dinner.


After dinner, we decided we wanted to rent an ATV. Many people on the island rent ATV’s as a mode of transportation. It is much easier than driving a car and is easy to get from one side of the island to the other. We rented it for thirty five US dollars for a twenty four hour rental. That night was amazing! We took our ATV to an outdoor, open Air cinema in Kalamari (a town nearby). The cinema was one of my favorite pieces of the trip. When we arrived, it wasn’t too busy. The vibe of the cinema was extraordinary.

The seats were like directors chairs and were lined up in rows facing a giant screen. There was no ceiling and plants were everywhere-near the front a small stage was filled with succulents, flowers and even a mini Santorini village. There were tea lights hanging from the posts and trees. The sky was pink as it began to set and the speakers were blasting old jazz music from the sixties. In the back, behind the seats was a bar with a full size popcorn machine and all the fancy drinks you could imagine. Jack ordered the local beer-Crazy donkey and I ordered a local wine. The movie that was playing was hotel Artemis which was perfect because it was one the two of us had never seen before. The Santorini breeze was cool, I was glad I brought a blanket for when the sun went down. The pricing was very reasonable here- only eight euro per person, and it is something I would recommend to anyone traveling to Santorini.


The next day, we woke up early and set out to explore Santorini ATV style! We had no real hard plans, but just wanted to spend the day out and about. We headed back to Perissa to grab my charger from the hostel we had stayed at the previous night. Afterwards, we followed the signage (which is pretty few and far between) to Red Beach. It was about a fifteen minute ride from Perissa. We were singing the whole ride there, having the time of our lives!


When we got to the beach, we had to hike up and then down to actually get to the beach. It was really pretty, but not very practical to get to. We couldn’t find a spot until the absolute end of the beach and once we got to it- it was not ideal to lay and tan on as it was extremely rocky. We set out our bags and sat on the rocks near the water for a few minutes but kept getting knocked over and splashed in the face. We only ended up staying for around twenty minutes. We then started the trek back up. Next, we headed to the Ancient Ruins of Atrotiri for a quick visit.

Red Beach .jpg

Afterwards, we stopped back at the hotel to get ready for the night ahead. We ate lunch, and headed to the Santorini wine museum. The Koustoyannopoulus winery has a walk-through museum exhibit that talks about the history of wine in Santorini.  The exhibit cost us 10 euro each. The exhibit is self guided and was completely underground. They gave us an audio device that allowed us to navigate through the winery ourselves. There are twenty exhibits that have 3-D scenes along with them. The moving 3-D figures were cool, but kind of creepy. It went through how Santorini’s economy thrives off of wine making. At the end of the tour, we got to sample four of their wines.

Atroki .jpg

We waned to end the night in Oia and decided to use the signs to navigate ourselves there. We took the back way and ended up driving around the entire coast of the island which was amazing.  We drove through the backside of Fira which was amazing because the back side of the island is much less touristy. It was extremely amazing and relaxing. After finding a parking spot in Oia, we headed directly to the main street of Oia. It was just as beautiful as I had hoped- and better. I have been dreaming of Oia for years and was just so excited to be there for the evening. It was so dreamy.


We walked down the street and enjoyed the view. I didn’t think Santorini could get any better until I turned around and saw Jack on one knee asking me to marry him! We enjoyed our engagement briefly with three cute Australian girls squealing about how sweet it was that they got to see it happen! Engaged, Giddy and in the most beautiful place in the world, we sat down and enjoyed a dinner with a view as the sunset. I honestly don’t remember the name of the restaurant because we were so excited about getting engaged! We ended our night by driving back to our hotel via the other side of the island. It was the absolute best day.

Our last day in Santorini we wanted to spend time on the water. Many of the private boat tours that we wanted to do were extremely expensive, so I spent hours and hours researching an option that was reasonable, but what we wanted. Prior to our tour, we headed into Fira and checked into our new hotel, Porto Castello. We chose this hotel because it was extremely affordable and offered a free shuttle into Fira and Oia. We booked a tour for 10:45 A.M. and headed to the Old Port. We took the stairs down to the port which took forever to get to. Note: If you are going to visit, PLEASE take the cable up or down, but please don’t use the Donkeys!!! We saw how they were being treated and it was absolutely horrible.


The boat tour we booked through Caldera’s Boats, was completely worth the money. We paid 35 euro each for a four hour trip that took us to the Volcanoes, the hot springs and the little island of Thirassia. We were able to feel the heat of the volcano and had a beautiful view of Oia from the island. We decided not to dive into the hot springs due to the fact that we only had a short amount of time to swim to them. The little island of Thirassia was the best part of the trip. It is a small island filled with locals. We ate lunch literally right on the water. It was beautiful and relaxing- the closest thing to island living! The water in the Mediterranean is the bluest and clearest water I’ve ever seen. That night, we ate dinner at the hotel. Our dinner was cooked right in front of us by one of the owners and it was the best meal we had in Greece! It was also the cheapest! It was the perfect end to a perfect few days.

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Santorini will always have a special place in my heart! I hope we are able to go back someday. The island was full of fun and adventure, and it was where we got ENGAGED! Until we meet again, Santorini!

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