Dreamy Santorini – My Perfect 5 Days Solo Island Trip

Santorini has been on my traveling bucket list for years; the white houses with blue roof tops kissing the blue sea and being sun-kissed at sunset. This September I realized the bucket-list wish and spent 5 whole days under Greek sky and sun, exploring Oia, Thira, Pyrgos and two stunning beaches – The Red beach and black Perissa beach, along with trying local Greek food and discovering that the island’s landscape and bay is far more beautiful and captivating than the white houses and iconic churches. Of course, I stayed true to my traveling code and even though I traveled to one of the most expensive and touristic places in the world, my trip was on backpackers’ budget and I managed to steal a few precious tourists free moments and views.

My Santorinian adventure begins with landing at 22.30pm in the Island’s airport, just 10 by taxi from the center. As there is no public transport at this time of day nor Uber on the island, I had to take a taxi and managed to join 2 other tourists and share a taxi. I had already known I am traveling to one of the most expensive places in Europe, but I was not prepared to paying 15 Euros for a 10-minutes’ ride! Indeed was quite a shock for me personally as all my previous travels were to South East Asia, and you can imagine the huge difference in traveling costs between Asia and Europe. Already from the short ride you could see that Santorini was something special and stunning in architecture, even at night. I quickly arrived to my hostel, Caveland,

I found the instructions and room key on the reception’s door, due to the late arrival time. Found my room, which I shared with 3 other travelers, and got my rest after the long traveling day. I woke up to a chili island morning and discovered the hostel as beautiful as described and captured in pictures. The breakfast included coffee/tea, fresh fruit, pastry and Greek Yogurt with Granola, jam/ or honey – not bad at all! I was ready to begin my first day on the island and headed to old town of Thira – the iconic views of Santorini. The hostel is about 20 minutes’ walk from Thira and island’s center. With signs everywhere, you cannot miss the turn uphill to the old town. The views i found before me took my breath away – The contrast between the dark brown mountains, vast blue sea and white houses, was postcard perfection.

Thira and Oia on the other side of the island, are extremely small and touristic. Finding a quite spot is a challenge. I spent the morning walking through the pathways in Thira and eventually decided to continue walking up and straight to Skaros Rock, passing on my way the petit village of Imerovigli. Santorini is full of churches and cathedrals, and they were my favorite architectural structures on the island.

All these magnificent churches were on the way to Skaros Rock, the most important fortress in medieval times. Today it is a rock formation of about 20m in height and very hard to miss as you see in the pics. From the main trail of Imerovigli, there are steps down the rock’s trail and a short path to a 360 degrees view of the bay, Aegean sea and other islands.

The view of Thira from the way to Skaros Rock.

It takes about 2-3 hours to reach Skaros from Thira, if you like stopping to admire the view and take some amazing pics, like I do, with my Nikon. It takes the same amount of time to go back to Thira, of course you can continue on the same path to Oia, but as it was a hot summer day in September, I decided to return and explore Oia another day.  On the way back I enjoyed local Gyro with fries and Tatziki – delicious traditional pita bread with grilled meat!

After a good night’s rest on the second day I explored the village of Pyrgos. I highly recommend getting there early in the morning – It is very small and at noon becomes packed with tourists. I got there at 9am with a local bus from Thira, it’s about 30 minutes by bus. I arrived to discover a sleepy village, waking up to a beautiful morning, overlooking the mountains and sea. In contrast to Thira and Oia, Pyrgos is a “living” Greek village, whereas Thira and Oia felt to me more like museums and made for tourists.

From the center I continued to another view point in Santorini. Profitis Ilias, a monastery, at the top of the highest village of Pyrgos. The hike takes about 40 minutes, on the way you will meet another ancient prayer house, and be sure to always turn around and admire the panoramic view of the island, 567 meters above sea level.

From Pyrgos I took the local island bus to the most beautiful beach in Santorini – The Red Beach. I ate a great lunch in a local tavern on the way to the beach, changed to my swimsuit and was ready to relax after the hike up and down Pyrgos. To get to the beach there is a short walk from the bus pick up point and it right behind the mountain’s corner.

I spent a few hours admiring the beach, the colors and dipping in the chili Aegean sea and absolutely loved it. So, if you have time to visit only one beach or want to spend a perfect day on a stunning beach – The Red beach is a must.

On my third day in Santorini I headed to Oia. When I was planning the trip to Santorini, Oia got me all excited, and indeed it’s beautiful, but much smaller than Thira and that means a lot more touristic and crowded.


Oia is perfect for souvenir shopping

and has another stunning view point, this time from the bottom, Amoudi Bay. There are about 240 steps taking you down to the port, so be sure you have comfortable shoes on and yes you will need to climb it all up, or take a donkey ride.

I chose to climb up, after having delicious gyro from lunch with the view of the bay before me- breathtaking colors, volcanic mountains in red and black, white houses and blue Aegean sea.

I ended another wonderful and tiring day in Santorini with a great dinner with a friend and view of the famous sunset in Fanari restaurant.

My last day in Santorini I dedicated to relaxing in black Perissa beach and capturing Santorini at sunset. First thing in the morning I took the local bus to Perissa beach and spent a quiet and relaxing morning watching the waves, admiring the black sand and being sun-kissed once again.

Santorini and its iconic sunsets…


So, Santorini in September is still very crowded, hot and humid during the day and chili in the mornings and evenings. It is absolutely captivating, stunning, and affordable. As much as it is supposed to be a small island, it is quite challenging to get around the island, between the villages and beaches, if you don’t rent a car or the popular moped. I traveled by foot or local bus, so for me 4 days were the perfect amount of time to spend on the island, although I have met others that spent 2 days and explored a lot by moped. Personally, I don’t like rushing through sight seeing and prefer taking in everything slowly and in my own pace, so I could really get a feel of the place.

My budget, including 5 nights in a hostel, meals, transportation and a few souvenirs, like leather Greek sandals for 30 Euros, was about 350 Euros.

Travel solo to Santorini

Greece is wonderful and Santorini was everything I had imagined and so much more.

Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s