by Ucman Scher
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Solo Gay Trip Guide to Santorini Island

To watch the sunset on Santorini from the curved slopes of Oia was a lifelong dream and finally, when I got to Santorini it was unbelievably amazing. This beautiful Greek island in South Aegean is a true marvel with its current shape gifted by a massive explosion some 3600 years ago.

The centre of what used to be a much larger island dropped some 300 meters below sea level to form a giant lagoon; ‘Caldera’.  The caldera is 12 kilometres wide and surrounded by really steep and high cliffs. The towns of Fira, Imerovigli and Oia literally lie scattered at the top of the cliffs overlooking the caldera. The views rank as some of the most dramatic in the world.

Read my country guide about Greece to find answers to all your questions for a comfortable trip.



I always download some documentaries on BBC to watch on the plane and it was a coincidence I downloaded this documentary about Atlantis. It went about how Plato based it on the ancient civilisation of Santorini and Crete and suggesting with possible proof that Santorini was the real Atlantis that mesmerized Plato to write the tale; it feels true when you’re there..

I stayed in Fira next to the bus station in a hotel which was quite nice and not overpriced even for the season. Half asleep I reached the hotel at 2am and 2 lovely dogs welcomed me. The staff was lovely and a smile at that time seemed worth more than a thousand ordinarily, the Greek hospitality…

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Day 1

Fira Bus Station –> Parissa Beach –> Perivolos Beach –> Akrotiri Red Beach –> White beach –> Fira Town Caldera

Perissa Beach

I woke up the next morning excited to run to the beach and took the bus to Perissa beach. Now beaches in Santorini are not like any other place. Based on the volcanic activity most of them are black or very dark grey with a few other colours. Pressia and its neighbour Perivolos are both black sand beaches or black beaches and the combination of blue-green water with dark sand is beautiful and very calming.

I found a small cafe and got myself some breakfast and afterwards just went for a dip and got a sunned and umbrella (€10) and took another nap, oh the joys of the holiday.

Perivolos Beach

I woke up slightly lazy and after a few songs decided to walk to Perivolos beach which was a lazy 20 mins walk away. The 2 beaches have no boundary and you will see plenty of people sunbathing, swimming or playing around. There was a centre for water activities as well that offered jet skiing and stuff, I was too lazy to bother so walked on.

Perivolos beach had this lovely cafe with hammocks and I spent the next hour eating some Greek and fruit salad there and taking selfies because why not!

Akrotiri Red Beach

Next stop was the Red beach next to Akrotiri for which I took a bus back to Fira and got off at the junction of xxx to change to a bus that goes to Akrotiri. The whole area is quite pleasant and the bus arrived in 15 minutes and then it was an easy 10 min ride.

Walk to the Red beach
First view of Red Beach
Leaving for white beach
Walk back to Bus station

White Beach

The bus drops you at the corner and you have to walk around 15 minutes to get to the red beach. It is located on the side of a steep cliff and the stairs are narrow and steep but the view was absolutely stunning. I stayed there for a bit to take the boat that takes you to the white beach and then to another black beach.

White beach

I got to the white beach which is a pebble beach on the side of another mountain but it was already getting late so didn’t get off there. It seemed a bit weird because you have to keep your stuff high over your head to get to the bottom of ladder which brings you to the boat, quite dangerous for a non-swimmer 😉

The beaches were beautiful and I stayed till the sunset with a walk between to the archaeological site of Ancient Akrotiri. I got to the hotel to change and applied some olive oil before shower all over my body to cool it down; a neat little trick I learnt from Greeks. It just leaves your skin smooth and takes the stress away completely.

Fira Town Caldera

I wanted to stay in and watch some TV but I met a guy from Grindr and we went for a little stroll through the old town, it was quite touristy but when we finally got to the other side of the town which slopes towards the port I just froze in my tracks, one of the best surprises of my life. I didn’t expect Fira to be that amazing, I was saving it for Oia.

Every step you takes seems to be in heaven and there is no limit on the number of times you can slap yourself to check if this is real. We headed to a restaurant and had some food with amazing views of Caldera followed by a quick check out the ‘gay’ bar Tropicana which had mixed crowd and slightly boring music so we decided to go for Shisha instead in the town. Gay nightlife in Santorini is not as exciting as Mykonos. Grindr population is far and there are just a few guys around mostly either arriving or leaving.

About midnight it was time to head to the hotel for some rest…

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Day 2

Fira Cable Car –> Fira Old Port –> Nea Kameni –> Thirassia –> Oia Old Port –>  Lioyerma Lounge –> Oia Caldera

Nea Kameni

After a quick breakfast, I ran to the Old Port of Fira to take the tour boat for the day. The tour takes you from Old port to Nea Kameni which is the small island next to Santorini and has a dormant volcanic crater followed by a little swim in the nearby warm waters and then lunch at the Port of Thirassia and finally to get dropped off at Oia’s port.

I would HIGHLY recommend that you take the cable car down from Fira to the port which is much more pleasurable than running down endless stairs that just left me sweaty all over and obviously tired. These stairs were not pleasant at all with donkey and horse poo and animals literally crashing into you in hoards.

I finally reached the port and the tour started after they literally just filled us in the boats. It wasn’t the type of intimate tour with good service; more like ‘book as many people as you can cheaply and just transport them from 1 point to another’.

The ride was pleasant though and we reached Nea Kameni and from there the walk to the crater started. It is a barren island with people allowed at specific point through specific routes due to the dangers of volcanic eruption so always stick to your group. After a gruelling but interesting walk, we reached the crater which was interesting for like 5 minutes and then everyone got busy taking photos with the views of Aegean, the neighbouring islands and the crisp light.


We headed back to the boat and stopped over at a small but beautiful spot for a quick swim in the warm water full of sulphur due to volcanic activity and finally off to Thirassia for lunch with a rumbling tummy.

Thirassia has plenty of small restaurants at the port to avoid going up the stairs to the actual town and I was too hungry to go through the hassle. I sat down for a lunch of fresh grilled fish and Greek salad and the owner’s cat invited herself to lunch with me but she was pleasant company.

The waters in Thirassia were crystal clear and I spent the next hour relaxing in the water, it just felt amazing with the sun shining and water splashing against my body in such a beautiful setting.

Oia Old Port

Finally about 3:30pm we headed to Oia and reached the port around 4pm, the first views of Oia from the sea are just gorgeous and I started anticipating how beautiful it actually must be up close. So we reached the Old Port in Oia from which you have the option to climb the endless stairs or take a donkey ride for €5 which I did and instantly regretted; partly because the steep ride upwards on the back of a mule tears your legs apart and every bump hits your balls but also because I felt instantly sorry for the poor animal and its fear of the herder.

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Slopes of Oia

Lioyerma Lounge

Finally, we reach the top and I headed to a cafe to get some juice and relax and prepare myself for the sunset and meet a friend I made through Scruff while still in London. A few more gorgeous pictures and finally I met my friend who was very sweet and took em to an amazing sunset lounge. It is called Lioyerma Lounge and it had a beautiful pool and it was surprisingly moderate in terms of prices so a dirty martini was added to the view which turned into 2 and then 3…

Oia Caldera

I have never felt so exhilarated by the sunset as much as I felt in Oia. The views are just breathtaking and I struggled to speak which my friend was thoroughly enjoying. It just feels like your soul is being replenished and everyone went absolutely quiet to see the beauty. I was lucky enough to have come early and secured a lounger for a more relaxed view. I will never forget that beautiful sunset…

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Finally, it grew dark and it was time to get some food and it is fairly difficult to choose where to eat, my friend knew a couple of Taverns and we got a place overlooking the Caldera with some scrumptious dinner after a blissful and beautiful day. A little stroll on the streets of Oia and a couple of soul-enriching songs later I headed to the bus station and an hour later I was in bed absolutely loving the day.

The last day was just a bus ride from Fira to the New Port of Santorini to take the ferry to Mykonos. The ferries are generally late but you can’t take chances and the waiting room is quite dainty, I would recommend a book if you arrive a little before or on time because you will need something to kill your time…

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