Long Weekend Break in Oia, Santorini

Picturesque blue domed churches and white-washed towns and villages perched on a cliff-top, high above the vivid blue waters of the Aegean Sea could only be one place; Santorini. For a long time now Santorini has been on my to-do list, but as you could probably guess, my to-do list is quite extensive. One Sunday afternoon I was looking back a few years to the relaxing weekend that I had spent in Corfu and contemplated returning. After giving it some thought over a glass of wine I decided that although I had a fantastic time in Corfu I should visit a new destination. I was quite drawn to the idea of visiting a different Greek island, so it didn’t take much persuasion to book a long weekend break in Oia, Santorini. 

Long Weekend Break in Oia, Santorini

Flight Time from London: The published flight time from London to Santorini is 4 hours and 5 minutes, but the actual flight time is around 3 hours and 30 minutes.

Airline & Airport of Operation: I flew to Thira Airport in Santorini on British Airways from London Heathrow Airport. British Airways operate this route five times a week from Heathrow Terminal 5 during the summer season. Currently return tickets Santorini during summer 2020 on British Airways start from £168pp in Euro Traveller and from £636pp in Club Europe.

Transfer Time to City: Thira Airport is located approximately 11 miles from the town of Oia and takes around 30 minutes by taxi or car. My Airbnb host arranged for private transfers from the airport to Oia at a cost of €40 each way. Upon arrival in Oia our host arranged a porter to show us to the accommodation and take our luggage.

Where to Stay on a Long Weekend Break in Oia, Santorini

After deciding to booking my flights to Santorini I started to look for somewhere idyllic to stay. I know a few people who have been to Santorini and they all recommended that I stay in Oia instead of Thira. After spending a long time looking at various hotels and villas I had a spark of genius; why not have a look on Airbnb for somewhere to stay. I’ve never used Airbnb before so it was a first for me, but after entering my dates I very quickly found the perfect place. The accommodation that I booked was called Yposkafo Jacuzzi House and including the service fee which Airbnb charge it cost around £300 per night for my stay. 

We arranged a private transfer from the airport with our Airbnb host, which also included a porter meeting us at the car to show the way and take our luggage which was a great idea as the the walk was along small cobbled pathways weaving through the buildings of Oia. When you get closer you have to walk down about 50 steep steps which lead you from the main pathway through Oia to the house. When you arrive at the house you approach from above and find yourself walking down a smaller set of white steps, past the jacuzzi which is located above the house, on to the main terrace which is in front of the house and looks out over Ammoudi Bay.

The views from the terrace and the jacuzzi on the level above were absolutely breath-taking. It took me a few minutes to drag myself away from the view to have a look around the actual house. When you enter the house you walk into a large living room area with a vaulted ceiling with two sofas along one side which could also be used as secondary beds. On the opposite side of the room were two archways, the first leading to a small but perfectly equipped kitchen and another leading to a cute dining area.

At the far end of the living room is a smaller arch leading thorough to the bedroom area, there were also two window openings either side of the arch which separates the living room from the bedroom area. Further on from the bedroom is the bathroom with a typical Santorini cave-house style shower with exposed rock from the cliff along the back wall to the bathroom. The decor in the house was very typical of a Santorini cave house with many modern additions.

Post from RICOH THETA. – Spherical Image – RICOH THETA

Post from RICOH THETA. – Spherical Image – RICOH THETA

Post from RICOH THETA. – Spherical Image – RICOH THETA

Post from RICOH THETA. – Spherical Image – RICOH THETA

Post from RICOH THETA. – Spherical Image – RICOH THETA

My Top Recommendations for a Long Weekend Break in Oia, Santorini

Hire a car and explore Santorini

If you don’t have much time in Santorini you may just stick to exploring Oia, but if you have more time and could spare a day I would highly recommend hiring a car (or a quad bike if you prefer) for a day and explore more of what this fantastic island has to offer. I visited a local car rental office in Oia and asked if they had any quad bikes or buggies available for the day but unfortunately they didn’t have a great deal left. They did offer me a convertible smart car for the day and I thought this could be fun, so I went ahead with this. The car cost €75 for the day, I took the car straight away at 10am and returned it later in the day. The man in the rental office said I could drop it back the next morning, but as I wouldn’t be using it during the evening I decided to return it that night before heading back to the house.

Oia is located at one end of the island, and in total it took about an hour and a half to drive to the other end of the island. Some key places I visited during my day were the Red beach and the Venetian lighthouse, which were located at the far end of the island. I also stopped in Thira and also at the Venetsanos Winery for lunch and some wine tastings. 

Visit Venetsanos Winery

One thing that I really wanted to do during my stay was to visit a winery, and Venetsanos Winery came highly recommended to me. Venetsanos is located about 10 minutes from Thira, in the opposite direction to Oia. You could spend most of the afternoon there, from sampling wines and enjoying lunch to taking a tour of the winery. As I only allocated one day to explore the island I limited my time here to a couple of hours.

There are two large terraces perched high on the side of the caldera where you can enjoy your food and wines. I decided to go for one of their sampling packages which included 6 tastings, 2 white, 1 rose, 1 red and 2 dessert wines for a price of €20. The wines were all very good, but my favourites were the red and the two dessert wines. I enjoyed these with one of Venetsanos sharing platters which included local cheese, cold cuts and bread, whilst enjoying the fantastic vistas over the beautiful blue sea of the caldera. Inside there is also a large museum area where you can look at various artefacts from their wine-making and the vineyard history. I had a quick look through here before my tastings and lunch.

Book a boat trip around the Caldera

One thing that’s was high on my list to do while in Santorini was to take a boat cruise around the caldera. There are many trips available to book online, as well as on arrival. I booked my cruise on Expedia prior to my trip, with a company called Sunset Oia. Sunset Oia offer two cruises per day, one that leaves mid-morning, and a second that leaves mid-afternoon and which offers sunset views from the sea. 

I booked the mid-morning cruise at a price of £80pp (the evening cruise costs £95pp), this included a BBQ lunch on board, transfers from your accommodation as well as free soft drinks and local wine. The trip time was scheduled to be 4 hours and 30 minutes and included three scheduled stops for a swim; at the Red Beach, Black Beach and the Volcanic Hot Springs. Due to sea conditions on the day we didn’t actually visit the Red and Black beaches but instead we stopped at two alternative beaches within the caldera. 

Although we didn’t stop at all of the planned beaches on our trip the ones that we did stop at were just as beautiful and it was great to be able to just jump off the boat into the crystal clear waters to cool off. The food on board was delicious with more than enough to go around. The wine didn’t stop flowing until we docked either! There were about 50-60 people on board my trip, with enough seating for everyone so it didn’t feel overcrowded. I thought this trip was really good value for money and I wouldn’t hesitate  to book it again. 

Food and Drink on my Long Weekend Break in Oia, Santorini

As we had a kitchen in our Airbnb accommodation I didn’t eat out for every meal during my trip, but I did have one very good meal during my stay, at a fantastic restaurant called Karma. I found Karma by chance while exploring some of the smaller pathways in Oia and luckily they had a couple of tables available when I arrived. 

Most of the tables in Karma were arranged outside in a beautiful courtyard setting, with trees, plants and small walls dividing the courtyard into more intimate areas. For my starter I enjoyed a delicious local dish of chickpea stew, followed by a lamb shank in Greek spices with a sweet potato and butternut squash mash and to finish some local Baklava. With dinner I decided to have a bottle of local red wine from the same grape which I enjoyed during my wine tasting earlier in the day. 

After my meal I enjoyed a glass of Metaxa which is a Greek spirit, similar to brandy but much sweeter. My three courses, wine and a glass of local brandy amounted to just over £50pp which was great value for such good quality food in such a beautiful location. 

On my first afternoon in Oia I found this fantastic little cafe and cocktail bar called the Meteor Cafe. The cafe was a two minute walk from our house and offered a large range of delicious cocktails. The cocktails cost around €15 each, which for Santorini isn’t a bad price. They have a lovely little outdoor seating area set along the main pathway though Oia. During my weekend break in Oia I went here a few times for drinks. 

Top Tip: If staying in Oia, try and book accommodation that looks out over Ammoudi Bay instead of the Caldera, giving you your own private vantage point for Oia’s famous sunset, rather than join the crowds hours before in the streets or at Oia Castle.

Currency: Greece’s currency is the Euro and at the time of my visited the exchange rate was around 1.1 EUR to GBP.

Weather: I visited Oia in early October and the weather was in the mid twenties and sunny for the majority of my stay. We did have a some rain on the morning I that we left. 

Best Time To Go: Santorini is a very seasonal destination. The island starts to come to life early April and then closes towards the end of October. The months of June, July and August are the busiest, and you can expect flight and accommodation prices to be extremely high during these months. If you want to avoid the crowds I would suggest visiting Santorini either at the beginning or end of the season, you will also find much more reasonable flight and accommodation prices at these times.

Recommended Duration: I visited Oia for three nights but considering the flight time and all the time spent at the airports either side of these flights made my time in Santorini seem relatively short. I would recommend a slightly longer stay to fully enjoy your time in Santorini, I think 5 nights would be a perfect length of time.

Conclusion: I think it’s fair to say that my weekend break in Oia, Santorini fully lived up to my expectations, if not exceeding them. My Airbnb accommodation was a beautiful, spacious space, with the most stunning views imaginable. During my stay I enjoyed some fantastic experiences, food and drink. My whole trip was stunning, and at the time of writing this review I have already booked to return to the same house next year, but for a longer stay.