Santorini: 5 Days in the Most Famous Greek Island


Is Santorini overrated?

We knew that the stunning landscapes and gorgeous sunsets would be lovely, but would we be surrounded by a Disneyfied version of Greek culture and unbearable hordes of tourists?

Santorini is one of the most famous holiday destinations in the world so it’s natural to have these fears. What we found was fakeness existed in certain areas, but authenticity and kindness always surrounded it.

View Our Summary

Day 1

  • Exploring Finikia
  • Watching the sunset in Oia

Day 2

  • Exploring Oia and Amoudi Bay
  • Dinner at Lefkes

Day 3

  • Trek between Oia and Fira

Day 4

Day 5

  • Boat tour to the Volcano, hot springs and Thirassia
  • Evening flight to Venice

Day 1: Catching our first glimpse of Santorini

Arriving at Athinios, walking through Oia and a colourful donkey outside Maria’s Place

We travelled to Santorini by Ferry from Milos and arrived in the early afternoon. Our Ferry stopped in Athinios, the new port. Along with thousands of other people, we were shuffled into vans to be taken to our accommodations. We were treated to beautiful views as we drove the winding road from Athinios to the main stretch of land, 260m above sea level.

Our destination was Finikia, a small town just outside Oia, known for having a local and authentic feel but within walking distance to the big draws of Oia.

Maria’s Place and Finikia

We stayed at Maria’s Place. A mid-range option that wouldn’t break the bank. We sacrificed luxury for location and customer service which is a good option in expensive places like this.

Maria, the guesthouse owner herself, was full of character. When we checked in she gave us tips on where to go in Oia, local restaurants and what to do around the island.

We went out for a short walk through Finikia and stopped for lunch at Meze Meze before getting ready to head out that evening.

Watching the sunset in Oia

The last rays of sunlight slowly fading away over Oia

That evening, we walked to Oia to witness one of the most famous sunsets in the world. This is one of the most romantic settings in all of Europe and there is a sense of cautious anticipation in the air. A lot of people are visiting Santorini on their honeymoons. You don’t want the place you’ve dreamed of visiting for years be disappointing, right?

It seemed like everyone on the island of Santorini had made their way out on this night to enjoy the sunset as well. There was a stark contrast between ourselves and other travellers to the glamour of these high-end restaurants and bars.

We foolishly made our way to the Byzantine Castle Ruins, the most famous place to watch the sunset from, to find a spot. That proved impossible.

After some time we found a quiet spot on top of a brick railing (with only a dozen or so others) to enjoy the beautiful view.

We’d have rated it a 10/10 if we had the view to ourselves.

Day 2: Oia & Amoudi Bay

Iconic Santorini windmill against the sunset, bells atop a church and view from the Byzantine Castle Ruins

The following morning we walked back to Oia to explore the area without the heavy crowd and to grab a cheap bite for breakfast. Not the easiest task in this part of the island but we eventually stumbled upon traditional Greek bakery To Fourni, located near the bus stop and main parking area. After devouring a couple of cheese-filled pastries we headed into the glamorous heart of Oia.

The majority of walls and surfaces in town are painted white. They’re painted from a range of soft, pastel shades to stunning, bright pops of blue. This creates that iconic look that the Greek Islands are famous for. The consistency of this look is remarkable.

The distinctive architecture and colour palette of Santorini

There are beautiful old churches to admire and the town is full of winding pathways and platforms to walk or climb up onto. All of these offering different views of the surrounding areas. It’s quite easy to find a spot here to be on your own.

You’ll catch glimpses into some of the ultra-luxurious villas and suites scattered around also. The vertical layout of town takes away some privacy.

We went back to the Byzantine Castle Ruins for a sweeping view of Oia. The area is surprisingly open and without too many fences to stop people from exploring. We saw some people taking full advantage of this and taking some incredibly risky selfies.

Exploring Amoudi Bay

Cliff jumping rock in the distance, views from the walk down and a Santorini donkey

Amoudi Bay can be accessed fairly easily from Oia. All that it requires is a 15–20-minute walk down 300 or so steps. The steps themselves, particularly at the top, have been polished to comical levels like much of the surface in Oia, causing people to often slip at the beginning. Something to keep in mind!

The walk down treats you to views of Amoudi Bay and the surrounding calderas. There are donkeys along the way which you can pay to take you up and down the steps. We politely refused that proposition.

When you reach the bottom you’ll see seafood restaurants, a dive shop and a pick-up and drop-off spot for some boat tours. There is also a ferry that can take you to Thirassia from here a few times a day. A cheaper option if you wish to explore that island than going on a boat tour.

Continuing past the seafood restaurants you will reach a rocky pathway. Making your way through here will lead you to a swimming spot where you can swim out to rock nearby for cliff jumping.

Dinner at Lefkes

Lena enjoying wine during golden hour at Lefkes

Lefkes, located in Finikia, offers traditional food in a contemporary, ambient setting overlooking the small town towards the sea.

The food is delicious and the staff are casual and friendly. It was a short walk from Maria’s Place but still within walking distance from Oia. We would recommend trying this restaurant, especially if you are looking to escape the crowds in Oia and want some delicious, modern greek food. Bookings essential.

Day 3: Trek from Oia to Fira

Overlooking an old, seemingly abandoned church, Imerovigli and Alex trying his best balancing act

The following morning we walked back to Oia to explore the area without the heavy crowd and to grab a cheap bite for breakfast. Not the easiest task in this part of the island but we eventually stumbled upon traditional Greek bakery To Fourni, located near the bus stop and main parking area. After devouring a couple of cheese-filled pastries we headed into the glamorous heart of Oia.

The majority of walls and surfaces in town are painted white. They’re painted from a range of soft, pastel shades to stunning, bright pops of blue. This creates that iconic look that the Greek Islands are famous for. The consistency of this look is remarkable.

A rooftop with a perfect view in Imerovigli

Given that we were staying in Oia, we started from the Oia side and made our way to Fira. I personally feel the trek would be better the other way around. Starting in Fira and finishing in Oia allows for you to start in a busier area where you can grab coffee and breakfast and then finish in more natural, quieter surroundings.

The walk takes you through Oia, Finikia, Imerovigli and Fira and has a constant view of the coastline and sea. Part of the enjoyment is that it's not heavily signposted. Although, at one point we followed a trail around a caldera that turned to a steep drop down at the end. Be wary of this and exercise caution. It may mean you have to follow a road for a while.

When you finish in Fira, there are a lot of options for brunch or lunch and plenty to see in the area too. Being the islands primary commercial hub too, you will easily be able to catch a bus to wherever you are staying on the island.

We were exhausted after the walk and only spent an hour so exploring Fira before heading back to Oia.

Day 4: Day Trip to Megalochori and Pyrgos

Around the town of Megalochori

Megalochori and Pyrgos are smallish towns located south of Fira. They are famous for their quiet, laid back nature and for the wineries that are nearby. Pyrgos was once Santorini’s capital city and both towns maintain a traditional and local charm.

The towns receive their fair share of tour groups during the day, however, so they are by no means untouched. They both maintain the distinct Santorini look and if you veer off the main roads in town you will be by yourself, free to explore and wander as you please. Be careful with that though, it’s easy to end up in someone's backyard The open and cascading nature of their town layouts make this an easy mistake to make.

Flowers in Megalochori

To reach these towns, we caught a bus to Fira and changed at the main bus terminal there. It’s fine to stop at either town and walk to the next one once you are finished as they are very close to one another.

Venetsanos Winery

An incredible view from Venetsanos Winery but a little windy

Venetsanos Winery was easily our favourite drinking establishment we visited during our trip to Greece. The decor is rustic and the layout is open, winding down several levels.

It’s possible to tour the winery itself but we didn’t have time. We ordered from the tasting menu and tried a few reds and a rosé. Keep in mind we aren’t wine connoisseurs, but I can safely say they were all amazing.

Our sommelier was a young, friendly guy from Athens who told us stories about his parties in Santorini and then invited us to a beach party later that night. We took a raincheck on that one but enjoyed his energy.

We also ordered a side of the tastiest vine leaves we’ll likely ever eat in our lives. They aren’t to be missed.

Santo Wines Winery

Wine tasting at Venetsanos Winery, The main balcony at Santo Wines Winery and the sunset view

To finish the day we headed to the nearby Santo Wines Winery for some more wine tasting and to watch the sunset, seemingly, once again, with most of the tourists on the island.

This is the more popular of the 2 big wineries in the area but we enjoyed Venetsanos Winery more. This place seemed to lack character. If it wasn’t for its location there wouldn’t be much to be said about it at all.

In front of where we sitting were a couple of aspiring influencers. For the entire hour we were there they recorded Instagram stories, took selfies, and asked staff members to take photos of them. We (and everyone around us) sat in awkward discomfort as we tried to enjoy the view of the sunset which was beyond them.

Too drunk to handle reading the bus schedule we arranged for a minivan to take us home to Finikia.

Day 5: Boat trip to the Volcano and Thirassia

Our evening flight wasn’t until midnight so we wanted to use our last day to see a different side of the region.

We took a budget-friendly tour out to trek the volcanic island of Nea Kameni, sail past a sulfuric hot spring and spend the afternoon in Thirasia.

We paid 45 euros each for our tour and you can pay a bit more to see the sunset in Oia afterwards. There are plenty of higher-end tours you can go on as well if you’re willing to splurge.

Trekking on the volcanic island of Nea Kameni

Views of the Sanorini skyline from Nea Kameni

There is a slight sulfuric smell in the air that lends credibility to what you’re about to embark on. The trek from the port to the top of the volcanic hill is quite flat and easy and should take around 45 minutes.

The highlights are the views across the sea towards Santorini. The turquoise waters contrasting beautifully against the volcanic rocks, luxury cruise liners and island of Santorini.

Our guide was very well informed on the area, although we, unfortunately, missed out on most of what she was saying as we were away from the group exploring on our own.

Exploring Thirasia

Rundown building in Thirasia and view of the bay from high above

The last stop is a portside town on the quiet island of Thirasia. There isn’t much to do here but there is a steep walk up the caldera that will treat you to some beautiful views, once again.

There are also some seemingly abandoned buildings at the top. Relics of a past attempt at turning this area into a tourist haven? Who knows. Its a mystery to us, for now.

There are places to stop for tea, coffee and lunch at the top. We finished the tour after this stop, getting off at a port near Finikia as the rest of the tour boat went off to watch the sunset in Oia (old news for us at that point).

Our next stop was Venice! Read about it here.

Last thoughts

Santorini was truly magical. We loved our time here and feel that there is something for everyone. It wasn’t the overrated tourist trap we feared it would be.

Being here felt like you were part of something too. There is a definite excitement in the air when you visit places of this magnitude as we mentioned earlier, and you’ll feel it during your entire stay.

Combine Santorini with one of the lesser-known Greek Islands, like Milos, and you’ll get a great sense of what they have to offer.

What we would have done differently

  • We didn’t end up going to any ‘typical’ beaches during our trip to the Greek Islands. Perhaps we should have dedicated a day here to do that?
  • Visited Thirasia on a day trip from the local port and had more time to explore. I feel there was more to this island that we missed due to our short timeframe that our tour had stopped here for.


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