In summer 2020, not long after travel re-opened, EasyJet released the most ridiculously flexible policy seen during the entire pandemic. If even one leg of a booking was cancelled, you could rebook onto any other route in Europe at any other time, regardless of the difference in fare. We decided to take a £35 gamble and book the cheapest, crappiest flights on one of the most over-serviced routes (think Luton to Alicante) in the hopes that the flights would be cancelled and we could rebook onto a more expensive route in the future.
And what a gamble. We regret only making one booking with this scheme in mind. Both legs of our faux flights were cancelled and we rebooked onto the most expensive route we could find at the most peak of travel times. London to the Greek island of Santorini over a week in May.
Why Santorini?
This is how we ended up in spending a week in Santorini. I had wanted to go for ages after one of my very worldly friends declared it her favourite destination in Europe. This scheme was the catalyst. We were also hoping to go when the crowds were sparse, with only the brave traveling during the height of travel restrictions and testing chaos.
Unfortunately this original trip was cancelled in May 2021 when the British government put Greece on their no-fly list. By the time we finally traveled at the end of May 2022, Santorini was HEAVING with tourists. As hypocritical as it is, given that we are, ourselves, tourists, it did change the trip. There wasn’t a local crowd (like we had experienced in Cinque Terre in August 2020, or Toledo in August 2021). It seemed the entirety of the island existed to cater to tourists. Authentic experiences were nearly impossible to come by. We watched spellbound and baffled as packs of travellers turned up with selfie sticks to take photos of themselves before the sunsets. Worse still was negotiating the professional photoshoots capturing these magically contrived moments.
All of this said it was an absolutely stunning place to spend a week. So clear your credit card balance (yes, everywhere accepts credit card, and yes, it is expensive – both unheard of in Greece) and book your hotel ahead of time to save yourself a good €1000 if you’re traveling at peak time.
Where to stay for a week in Santorini
We stayed in the heart of Fira / Thera, overlooking the famous volcanic caldera, at a place called Hotel Theoxenia. We booked this hotel for the location but also the stunning pool and lounge area advertised where we could sweat off our hangovers in style. When we arrived we discovered that this is actually not part of the hotel itself, but about a block away at its luxury sister hotel, Aressana. The nightly price here was about four to five times the price of Hotel Theoxenia. We were thrilled with this arrangement. We’re very happy to stay in basic rooms as long as they are clean, but the amenities of the pool and gym were available to us as if we were staying in the five star hotel.
Getting around Santorini
As a happy accident it was also about a five minute walk from the bus station. This became the reasonably priced starting point for all of our day trips. Whilst getting the bus back to town was a bit of a struggle, the departures from the main station were reliable and punctual. Taxis in Santorini cost an absolute fortune. Whilst it is easier than you might think to call one (with many drivers treating Whatsapp like Uber), as soon as you step into one, you’re going to spend €20. Even if the drive is five minutes. End of story. It’s painful.
As so often with our travels, we had a GetTransfer waiting for us upon arrival at the airport. This taxi to the base of the hill on which our hotel was situated was €15. We had already booked our transfer back before we realised buses were such a good option.
Given the expense/inconvenience of getting around a relatively small island, and since we had over a week to explore, we decided to visit each small area on the island as a day trip and centre our travels around local restaurants and vineyards.
Day 0 of a week in Santorini
We flew into Santorini in the morning, landing at about 2pm. We headed straight to the hotel to drop our bags, however due to a Covid “incident” in which the previous guest to our assigned room tested positive that morning, we were upgraded to the Aressana hotel down the block for a night. At the time this seemed terribly inconvenient – all I wanted was to lie in the sun and eat Souvlaki – but it was actually a big upgrade.
Lunch at Lucky’s
After this brief detour, we beelined for Lucky’s Souvlaki. Lucky’s is a fantastic gyros/pita shop located right at the centre of town. It was about a four minute walk from our hotel and another two from the bus station. Santorini is an expensive place and we took full advantage of eating somewhere that was both delicious and cheap. This was our inaugural of many trips to Lucky’s. Lucky #1. We only ate the pork gyros. Just €3.20 a piece for gyros on fluffy pita and another €3 for a tallboy of Alfa. Dreamy.
Drinks at Tropical Bar
After a few hours chilling in the sun by the pool, we hit the town for drinks overlooking the famous sunset everyone is always going on about. Everything with a view looked tacky or touristy or expensive. We were about to give up and go for a walk around town when we passed a door that seemed to lead straight onto a terrace with space only for a line of stools overlooking the ledge. It was Tropical Bar, and it was ideal. A small, dark mahogany Greek dive that was equal parts terrace and interior bar. To top it off, it served Mamos. Mamos is our favourite Greek beer by a landslide, and a bit of an obsession of ours. We wound up coming here a lot, too.
After discovering these two gems – both destined to to see our faces on an almost daily basis – we had our first dinner at Argo. This also overlooked the famous Santorini sunset and caldera, but not quite so spectacularly as at Tropical Bar. Argo wasn’t cheap but portions are large. I would not recommend ordering more than one starter between two if you’re going to get onto the mains. We definitely ordered too much and whilst rising to the challenge we nevertheless went straight to bed after the meal. They had a nice wine list including some half bottles which allowed us try a couple of things.
Day 1 – Exo Gonia
For our first day trip we hopped on a bus and went to the base of Exo Gonia to start work on the vineyards of the island. Our first stop was Estate Argyos. A tour of the vineyard with a tasting of four wines and a small food pairing cost €15.
It’s customary in Santorini for drinks to be served with pieces of stale bread rusk and tomato paste – in the same way that a round in Italy would come with olives. We were confused by this offering at Argyos, but got used to gnawing our way through this local delicacy pretty quickly.
The setting for the vineyard is beautiful and the location is easy to get to from Fira. Not far off, you can visit the Donkey Brewery taproom, which was unfortunately closed on the day we went.
Lunch at a vineyard
After the tasting we walked towards lunch via the hilltop village of Exo Gonia. Google Maps said this would be a fifteen minute walk, but reality taught us it’s actually forty-five. It was blazing hot and I wanted more wine. The uphill would never end. Finally we made it to the top. A beautiful and tiny little village with a signature blue domed church. Only to find that the two restaurants (Metaxi Mas and Anemoloos – more on these after a second trip back up the hill) were closed. Apparently small and sleepy Greek towns didn’t open for business at 12:01pm.
We walked down the mountain and finally reached Aroma Avlis, the restaurant of the Artemis Karamolegos winery. It was inexplicably empty on a Sunday lunch, but the top-end food was fresh and served overlooking the vineyard itself. Afterwards we had a tour of the grounds and tasting of four of the wines for €15. As well as the wine production and the vineyards they also grow many ingredients for the restaurant in their gardens.
Next we decided to go to the Wine Museum, about a 15 minute walk back along the highway towards Fira. This museum was… quite the experience. We suggest buying the entry level package, having a quick walk around, and making sure you haven’t become too accustomed to some of the island’s more excellent wines before this tasting, as here they’re really not the best. The rusks were the stalest of the week. But to be fair it was a museum.
Dinner in the village
From here we desperately needed a beer, and found a local restaurant on the side of the highway serving Mamos. We had two and tried to find a taxi ride under €20 back up the hill to the restaurants. Several futile WhatsApp chats later we opted for the 20 minute climb back up the hill to Exo Gonia village.
After stopping briefly at Metaxi Mas to make a reservation for a table on their mountainside patio for later in the week, we continued to the less popular but equally good Anemoloos. Here we enjoyed one of our favourite meals on the island, and our #1 favourite wine, a white from Thessaloniki. The server was clearly the owner, an old man with a good amount of sass and charm. The saganaki (a square of fried cheese) was on the funky side and served with a sprinkling of sesame seeds and honey.
We fumbled back down the hill in the dark and waited at the side of the road for a bus back to Fira.
Day 2 – Oia
There’s an 11km walking path (some might call it a “hike,” but it’s not) from Fira to Oia. We got lucky and had scheduled this for the coolest morning of the week. It would have been a bit painful in the blazing hot sun we experienced on other mornings.
After our traditional breakfast of yoghurt, honey, chopped fruit, and filo delicacies, all served on the rooftop of our hotel, overlooking the caldera whilst accompanied by little birds, we set off for Oia.
It was about one kilometre from central Fira to Firostefani – a neighbourhood of Fira with its own village-feel. Beyond this point you really get a sense of just how popular a holiday destination Santorini is. We walked past thousands of hotel rooms built into the side of the cliff with no real connection to a town. As we got further away from Fira, the hotels started to become more luxurious and started including words like “concept,” “wellness,” and “retreat” in their names. After we passed those, we saw swathes of construction workers building what was surely an extension of this endless accommodation.
It took about 90 minutes for us to get to Snack Shop. A simple pitstop for fellow trail walkers. The offering is coffee, cake, and beer (of which all three were consumed).
Lunch and vineyards in Finikia
Our next stop was Finikia. Finikia is a small town which was a bit out of the way of the trail we were walking, but we had our eye on a nearby vineyard and there were a couple of nice restaurants in town. We ate at Krinaki, a beautiful local restaurant with a shaded terrace and excellent food. We had our first smoked eggplant of the trip here, which became a regular order for us as well.
After lunch we walked another 10-15 minutes to Sigalas . People we met at the other vineyards had suggested that this was one of the best on the island. The setup was modern and sharp and the setting beautiful. We each ordered a tasting. I got four different white Assyrtiko wines, and Sam got a flight of different wines, including a Vinsanto. Assyrtiko is the famous local white grape grown on the island, it is very rarely found outside of Santorini. Prices are high due to short supply, but it is well worth getting to know this grape. Vinsanto is a lower alcohol sweet wine primarily made with sundried Assyrtiko grapes (not to be confused with the Italian Vin Santo).
Onwards to Oia
They were all delicious (albeit pricy) and we stayed for a glass of our favourites after the tasting. By this time it was pretty late in the afternoon. We’d had two beers and a few glasses of wine, and we still hadn’t finished the trail to Oia, the most famously beautiful neighbourhood on the island. Nevertheless – like two moths to a flame – when we spotted a bar back in Finikia with a Mamos fridge we grabbed another beer before getting back on the trail. Oops.
Sunset and dinner in Oia
Our first photo in Oia was timestamped 17:28. It really was beautiful, but the streets overlooking the caldera were so outrageously packed with tourists, you literally could not move without walking into someone. We stopped for a gyros at Oia’s most famous grill, Pitogyros. It was good but not as good as Lucky’s, and at about twice the price. This was kind of the theme of Oia… beautiful, but not as good as a counterpart elsewhere on the island, and twice the price.
We walked around and stopped for another drink before walking down the cliff via stone cobbled stairs to a fish restaurant right on the water. The stairs on the walk down were crowded with tourists eager to watch the sunset. There were donkeys and the people peddling their services (you could ride one up/down the stairs for a price). There was A LOT of donkey poo. You really had to choose your footing to negotiate the poo. Avoidance was futile on the way back up after dinner, when it was dark. You just had to accept that you were going to step in poo.
Dinner was at Katina Fish Tavern right at the bottom of the cliff/on the water. We watched as boat after boat of tourists rocked up to the dock 20m away. We had some Mamos and Sam picked a whole Dentex for us to split. While it wasn’t great value, it was delicious and probably would be considered great value for Oia. We were treated to baklava and ice cream when we got the bill.
Day 3 – Boat Cruise
We bought tickets for a boat cruise a few months prior, as we had a £30 Viator cashback offer on our Amex. With hotel pick-up and drop-off, lunch on the boat, and an open bar, it cost us just shy of £70 each.
I am not really a boat person (I get quite sea sick) but often on island trips we like to do a catamaran cruise to get a view of the island we’re visiting. This was a particularly good cruise for this purpose, and we saw volcanic rock and even swam in the caldera’s sulfuric hot springs (sadly Sam’s swim shorts were sacrificed for this swim). Our photos are lacking as we were based on the front netting of the boat, and decided not to risk dropping our phones into the water. We would highly recommend this as a day trip!
We had dinner at cheap and cheerful Parea Tavern in downtown Fira and drinks at our local Tropical Bar.
Day 4 – Pyrgos
Pyrgos is the inland poster town of Santorini. A sloping little town of white stucco and blue domed rooftops. The day started like many others – with a trip to Lucky’s before catching a bus.
After a walk around the picturesque town we stopped for lunch at Penelope’s, which was alright but not the best. We bar hopped our way over to Metaxi Mas. This is arguably the most famous restaurant on the island with a ‘terrace’ overlooking the arid fields of the island which lead into the sunset. It was good value and the food was delicious. We shared four dishes between the two of us and they were all unique and excellently prepared. For the second time on this trip we walked down a dark hill and waited on the side of the road for what felt like forever for the bus home.
Day 5 – Megalochori
This was a serious day of vineyard hopping. We set off for Megalochori by bus for an 11am tour at Boutari Wines. Here we had one of our favourite tastings. It was €20 for six truly excellent wines, and whilst it didn’t come with much of a tour the experience was excellent.
Lunch in Megalochori
Next we headed into town and stopped at literally the first restaurant we came across – Mousiko Kouti. The food was delicious but being charged €6 for a 330ml Mythos left a bitter taste in the mouth. We had a meat and potato dish which was wrapped in a baking sheet and cooked all together, and a set of fried tomato balls which we loved so much. It was here that we had possibly the best stale bread rusks of the trip.
Lunch was great but continue walking another block and you’ll find Raki, where we drank 500ml Mamos beers for €5. The dream. Here we had some more tomato balls for a snack, and the rest of the food looked really good too.
After a walk around the beautiful town we headed to Gavalas for our next tasting. There were no vineyards here, and while there was an old winery, the tour was pretty limited. The wines were fantastic though and our guide was very knowledgeable. Be sure to have a glass of their flagship Santorini Assyrtiko in the blue bottle. A bit tacky but the product is delicious.
We then trekked to Santo Wines where the views were stunning but the wines were meh. Definitely save this for last to maximise the view / be too drunk to remember the wines anyway. We were dumb and missed our bus home, but caught a €20 / 10 minute taxi back to town (aka Bar Tropical).
Day 6 – Fira and Firostefani
We had done a lot of getting up and going on this trip, so we took the morning to chill out by the pool and catch some rays. We had Zotos gelato for breakfast (expensive – €5 per cup), which was authentic and high quality gelato. I am a bit of a gelato snob and, having run a gelato stand for a summer in my university years, I know how to spot the real thing from the crap. This was the real thing, amid many places serving a lot of crap.
After a chilled out morning (and a Lucky’s, obvs) we walked to a local to Fira winery, Anhydrous. Here we got a tour of the premises including their egg shaped fermentation tanks, amphorae, and foudres.
Our guide was notably energetic and the setup, similar to Sigalas, was modern and high end. We had a couple of glasses of wine each, including a €20 glass of their rare Icon, which was worth the price tag, especially with our mad server’s generous pours. At this point we were desensitized to Santorini pricing, and anything that was on par with London pricing seemed reasonable. But €50 for four glasses of wine in Greece is really not standard pricing.
Dinner in Firostefani
We had dinner at Aktaion in Firostefani, a great little restaurant which was celebrating its 100th year. The food was excellent and we ordered the tacky blue bottle of Gavalas Santorini. We managed to snag seats on the terrace overlooking the sunset, and were served some potent honey-based booze at the end of our meal. Result.
On our way back to Fira we spotted the unimaginable… Mamos on tap at some random bar serving people on the street, not having any chairs of its own. A bewildered Sam asked the bartender if they served Mamos on draught, to which the bartender replied “yes, that’s why there is a Mamos badge.” We got two beers, which Sam was convinced were not, in fact, Mamos.
Day 7 – Akrotiri
After our morning ritual of waiting for Lucky’s to open and walking to the bus station, we took the bus to Akrotiri. Here we visited the archaeological site of a prehistoric town. The town was buried and preserved in pumice following the Minoan eruption – one of the most powerful volcanic events in human history. Admission was €12 each and it was worth it and interesting to see.
Outside of this site, Akrotiri is famous for its red beaches. We walked to the water and admired these from afar, and opted to get lunch instead of sunbathing.
Lunch in Akrotiri
We ate at The Cave of Nikolas, which was one of our favourite restaurants on the whole island. They had their own farm where they grew their produce, and they had a display of fresh fish on ice. Sam selected our fish from the display and we had a whole red snapper to ourselves along with the best smoked eggplant and tomato balls on the trip (which is saying something).
We had a beer at the bus stop while we waited to go back to Fira. If only all Santorini bus stops were like this. Hopping off the bus about a 15 minute walk before Fira you can visit the Ftelos brewhouse and taproom. What a space. They obviously sunk a lot of money into the layout – but we spent a lot of money on subpar beer. If you are visiting from the US, UK, or anywhere with a progressive craft beer scene… give this a miss. We wound up not finishing a lot of the beers we ordered, and pined for cheap and tasty Alfa or Mamos.
We walked back to Fira for one last night overlooking the caldera at Tropical Bar, and only moderately regretted the margaritas we ordered.
Day 8 – final day of a week in Santorini
We spent our last day vegging out by the pool, drinking Alfas, and feeling fat and depressed about going home.
Before heading to the airport, we visited Naoussa, a restaurant on the ‘other’ side of Fira. Here there was a reasonable compromise between price and the premium outdoor seating overlooking the famous sunset. The restaurant owner needed to inflate pricing further given that he must have smashed an entire box of dinner plates during the meal, shouting ‘OPA!’ after each write-off. The most entertaining part of this was seeing how unamused the rest of the staff were as they navigated a packed terrace covered in smithereens of broken plates, contemplating the cleanup job to come. Their customers really seemed to get a kick out of it though.
So there it is – a full, indulgent week in Santorini. It was easy to spend as much time as we did there, but you could easily condense this vacation into four or five days if you shake a leg. We really enjoyed being able to hop on a bus to all of the island’s main destinations and would highly recommend the hotel that we stayed at for both location and sister hotel amenities. If you’re doing a big trip to Greece, Santorini is definitely worth at least a few days. Whilst it isn’t the most authentically “Greek” experience it is a beautiful and unique island, and it became as popular a destination as it did with good reason.
