Santorini has been at the top of my travel wish list for years and the main reason I’ve always wanted to visit Greece. Flipping through travel magazines and seeing those white churches with the bright blue domes sitting high up on the Caldera made me want to book a plane ticket there immediately, and yet, somehow it’s taken me years to finally do it. Thankfully, when I first saw Oia, it was everything I imagined and more!
Walking along the cobblestone streets was like stepping into the photos of the travel magazines that made me dream of coming here. The contrast between the white cliff of Cycladic houses perched 300+ metres up at the top of the Caldera and the beautiful deep turquoise Aegean Sea shining below was breathtaking. I was immediately in love with all the blue doors and shutters and colourful flowers, such a striking contrast against all the white.
The island of Santorini surrounds the vast crater left by one of history’s largest volcanic eruptions, with smaller islands found around the western edge. The sunsets hitting the snow-white buildings give the whole place an orange-red glow and are definitely not to be missed!
We spent five days in Santorini, the first three at an Airbnb just outside Oia, in Finikia, and the last two in Fira.
Oia, located on the northern tip of the island, is a must-see when visiting Santorini. Restoration work after the earthquake in 1956 has turned this spot into one of the most stunning places in the Cyclades. Built at the top of the steep Caldera, bright white buildings are nestled into the dark volcanic rock and the contrast is stunning. Today, the often-narrow streets are lined with shops and restaurants. Boutique hotels and Airbnbs can be found built into the sides of the Caldera. Spend your time exploring the labyrinth of streets here, finding the iconic blue domes and numerous churches.
While not much remains of Oia Castle after the earthquake, the ruins of the Venetian Castle of Agios Nikolaos is worth a visit for the views alone. This is also one of the most popular places to watch the sunset.
Over 250 steps below Oia, you’ll find Ammoudi Bay. The walk down is full of beautiful views of the dark-red Caldera with its snow-white peaks looming above.
Several fish tavernas are found down here, making it a perfect spot to enjoy fresh fish for lunch or dinner. To get back to the top, you can take a taxi or ride a donkey … or just hike it like we did and get your steps in!
Another must-do in Oia is a sunset cruise. There are many tour options ranging in size, price, and number of participants. We went with Barbarossa Sailing, and are so glad we did. We sailed out from Ammoudi Bay and went snorkelling in the Caldera and spotted the tiny church built in the rocks at sea level and saw the boats hidden in caves for protection, sailed around Santorini, checking out the various rock formations and the old port of Fira.
We stopped for another swim in the hot springs by the newest island (still over 500 years old) before having a delicious dinner made by the crew onboard and then sailing back out into the water to watch the sunset, which was amazing over the water. (Have I mentioned that the sunsets here are not to be missed??) The cruise ended back in Ammoudi Bay, which all lit up at night is also a must see!
From Oia, we moved to Fira, Santorini’s largest town. Views from here are amazing as you’re in the middle of the island and able to see both edges of the island’s moon shape.
Much like in Oia, the Caldera’s edge is filled with layers of hotels, restaurants, and cave apartments. The narrow cobblestone streets twist and turn as you make your way up and downhill.
The old port of Santorini is 587 steps down from Fira. Here, along with walking or taking a donkey, you can also ride the cable car and enjoy the view.
Following the Caldera’s edge, you can walk to the neighbouring town of Firostefani, filled with more beautiful views and great restaurants to catch the sunset from. Anywhere along the edge here offers beautiful views of the island, the sea sparkling below and, of course, the sunset!
Also be sure to stop by The Church of the Three Bells of Fira, one of the most photographed Greek Catholic churches on the island, also known as the Church of the Ascension of the Blessed Virgin Mary. While it can be a bit tricky to figure out how to get up, the view from the top is a must-see.
As one of Greece’s most important producers of wine, no trip to Santorini is complete without touring one of its wineries. Here, they are known for fresh dry white wine made mainly from the assyrtiko grapes of the region, and I couldn’t wait to try some.
We headed to Santo Wines for a tasting with a view. They have several different tasting options available. I opted for the 7 Premium wines and was quite happy with my decision! Our server gave us a brief history of the winery and some info about each of the wines we would be tasting, but if you are looking for something more in depth, tours are also available.
And of course, the food here is amazing. If you want a sunset view along with your dinner, be sure to arrive early or make a reservation. A few of our favourites were Piatsa Souvlaki Grill House, a cheap, delicious spot near the Oia bus stop with gyros, souvlaki, tzatziki and pita and more; Terpsi N Oia, a fancier spot where we enjoyed a great breakfast with a gorgeous view over the Caldera and the 3 blue domes in Oia; and in Firostefani, we had an amazing meal with a sunset view at Vanilia Mediterranean Cuisine.
Tips and Info
Santorini is a popular cruise ship stop, especially in Oia and Fira. To help avoid the huge crush of cruise ship passengers that flock here starting mid-morning, head out early in the day and then back out in the evenings. This is also a great way to beat the heat, as shade is almost non-existent here. Plus, if you’re looking to get great photos before both the crowds and the sun hit, 7 a.m. is a great time to be out exploring!
A cheap and easy way to travel both around the island and to and from the airport is by bus. Most rides cost less than €2 and buses run on a fairly regular schedule during the high and shoulder seasons. Buses all have luggage areas too, making it a much cheaper alternative to taxis. More info can be found here.
Ditch the heels as the cobblestone is very uneven and you are constantly walking up and down stairs and hills.
If possible, avoid high season, when crowds and prices are both at their peak.
Oia is a must, but accommodation prices here are definitely at the higher end, especially during the high season. So, while I would have LOVED to have a place right on the side of the Caldera facing the gorgeous sunset, based on booking last minute and the $500 a night and up price tag, we opted to stay just outside of Oia in Finikia, in our own Cycladic-style house. Then we’d walk about 20 minutes into Oia each day. This is a great option if you are unable to book well in advance or are looking for cheaper accommodations.