Santorini is a scenic, Insta-perfect paradise where the views really do live up to the hype and the sunsets are like nowhere else. The island was formed by 4 volcanos with the middle one still peeking through the water in the center of the caldera (large, cauldron-like hollow). This is how we spent 4 sunsets in Santorini, Greece. We took a fast ferry from Mykonos to Santorini. Be sure to book your ferries between islands in advance!
We rented a car which is a good idea if you are in Santorini for more than 2-3 days, a car is needed for at least a day to get to the beaches towards the South and have more freedom to explore other areas of the island.
Day 1
We stayed in the Northern-most scenic part of the island, Oia (pronounced ay-yah). Oia is known for its white cliffside villas that are stunning during every part of the day. We went all-out with an air BnB at Skala Caves. It was definitely the best in terms of location, positioning of the view of the water, caldera, and other cliff side caves.
We stopped by the to-go cocktail spot The Boozery and took the stairs followed by a hike down to the shore overlooking the tiniest island Nisis Agios Nikolaos where Ronak and Don went on a spontaneous swim.
We were craving Asian food and found Paradox Thai which hit the spot.
Day 2
We woke up early in the morning to beat the long lines to take pictures around the town, cliffside, and amongst the blue-dome churches. If you make it out before 7:30am you should generally be fine! Thanks to our dear friend Don for the fabulous pics.
We then headed back to change into hiking clothes and had a nutritious breakfast at KooKoo Bar before our long, active day.
The hike from Oia to Fira (Thera) was very long and scenic. It ranged from mild to moderate strenuousness so I definitely recommend proper hiking shoes. Along the hike we discovered more high-end cliffside caves and villas, as well as resorts situated away from the touristy alleys of Oia. We picked up some of the sweetest locally-grown strawberries and passed by Skaros Rock.
We explored Fira which was a lot more crowded and less scenic but still had the Santorini feel. I would definitely recommend staying in Oia versus Fira. We ate the most creamy hummus of the trip as well as a delicious gyro at Why Not, and grabbed another to-go cocktail at the Fira Boozery location.
The main strip of restaurants included Solo Gelato. We actually came back to this area on our last day to try Yogi which ended up serving the best gyros we had on the whole trip. We then took a bus back to Oia.
Upon return to Oia we enjoyed our jacuzzi, and got food from again from Paradox as well as the best gyros in Oia from Pitogyros Traditional Grill House.
Day 3
Breakfast at the Karma was delicious and aesthetic. We stumbled upon the most quaint, must-stop bakery in Oia Fourni Bakery where I picked up a baklava.
Santorini is not particularly known for paradise-like beaches but they are definitely worth checking out, such as the Perissa black sand beach. The water was almost as cold as it was in Mykonos!
At Perissa we stopped by Aqua Restaurant which had the best tasting hummus of the trip, and they even had vegetarian moussaka. We then visited the interesting formations on Aspri white sand beach. There is also a red beach that we did not make it to.
We walked around the boutiques and restaurants in my most favorite part of Santorini, quaint town of Pyrgos.
Our last destination was Santo wines. There are a multitude of wineries in Santorini. Santo Wines is classy with good views of the caldera, and we tasted two flights for a total of 13 different wines.
We got back that evening just in time to take (the very important) sunset pictures. Be prepared for a massive crowd and very little space to take pictures on the Western sunset sides of the island. Go to the Oia Castle, the Oia Windmill area, or grab a good spot on the sidewalk/stairs with a perfect view of the setting sun as early prior to sunset as you can!
Instagram vs. reality!
Our fancy dinner night was at Roka, which offered a refined but still homey feel. Although we were able to leave and come back after our one hour wait, I would recommend making a reservation in advance for after-sunset time as that’s when people flock to dinner!
Day 4
We left the AirBnB and drove back to Fira for their multitude of lunch options and last-minute souvenir shopping. Drove to Art Space Art Gallery – Winery – Museum where we learned we needed a reservation, I would highly recommend doing this in advance based on the museum and quaint vibes from the spot, I really wish we could have checked it out.
We ended our trip with dinner at Metaxi Mas, the most strongly recommended restaurant to us for which we actually had a reservation. It was a very quaint, authentic experience that I think would be nice pairing with a stroll through Pyrgos and a couple hours at Art Space!
This post was all about how to spend 4 sunsets in Santorini, Greece! Santorini truly a wonder and worth a trip combined with other Greek islands for the perfect vacation. Check out my post on Mykonos!
