Santorini: Bold, beautiful & absolutely worth it – Oia travel guide

A TRAVEL GUIDE TO SANTORINI ISLAND, GREECE
[PART 3|3]

Santorini Oia guide




Once a stronghold of the island’s seafarers, the charming village of Oia is Santorini’s North Star, almost as famous and bright as Santorini itself. A walk around Oia will have you thinking that we perfected architecture and town planning centuries ago. The locals made the best of the harsh natural environment of their island and created a place to live that resembles those of fairy tales. It does make you wonder, why oh why do our modern cities look the way they do?

Whether you have selected Oia as the base for your trip to Santorini or just visiting for the day, this is my list of the very best things to do, see and experience in Oia. If you are travelling slow, you can spread things out into multiple mornings, afternoons or evenings. Visiting just for a day? Towards the end of this post, I talk about how you can slot all my suggestions in one very full but fulfilling day! Let’s get started!

Travel map
Santorini:
Travel map
Geographic location:
South Aegean Sea, Greece

Island group:
Cyclades

Area | Population:
73 km2 (28 sq mi) | 15,550

Capital town:
Fira
During the Neolithic era (before the volcano eruption which caused the partial collapse of the island mass and the creation of the caldera), the island was called ‘Strongili’ (meaning round) due to its (then) shape. Later, the island’s name was changed to ‘Kallisti’ (meaning the most beautiful).

The name Santorini came about in the 13th century from the Venetians, as a contraction of ‘Santa’ and ‘Irene’, an old catholic cathedral. Nevertheless, the official name of the island remains to this day ‘Thira’ after its capital town (which has been paraphrased to Fira).
Santorini Greece Travel Map
Apoplous Greece Map Cyclades Islands

(click on the maps to enlarge)

Know before you go
Santorini:
Know before you go
BEST FOR:

Those on a once in a lifetime trip to Greece, couples on a romantic holiday and anyone who ever looked at a photo of Santorini and thought that this is a place they want to visit, because *spoiler alert* the real thing is even more stunning.

Landscape & architecture

Simply unique! It’s not an exaggeration to say that there is no other place on this planet like Santorini. A spectacle of Cycladic whitewashed houses and colourful cave houses perched on the black and reddish cliffs around the electric blue caldera.

Beach doodle 500
Beaches

The island’s beaches are volcanic, featuring lunar landscapes with long stretches of black sand and crystal clear water. And then there is the martian landscape of the red beach with its emerald waters and tall red cliffs.

Island vibe

Wow, wow, wow. Get ready to be dazzled by the beauty, drama and energy of Santorini. In high summer, there’s wedding celebrations & proposals happening everywhere! The crowds and high prices are real too. It’s worth it though, I promise.

Tips

If you are only visiting for a few days, you can rely on public transport and taxis to go around (the villages themselves are vehicle free). However, if you truly wish to explore the entire island and its beaches, consider hiring a car, moped or ATV.

Best time to visit

Early June to late September is the best time to visit the Greek islands. Santorini is quite crowded during July & August. If you don’t care about going to the beach and wish for complete peace & quiet consider visiting in spring or autumn.

Practical info

For things to know about Greece including currency, plugs, language & visa requirements, head to:

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There is so much to say about Santorini! In this blog post, we are focusing on the charming village of Oia. However, there is another post, my Santorini trip planning guide, which covers practical information about the island and also a blog post about the top 7 experiences, sights & things to do in Santorini. If you are thinking of exploring what lies beyond Santorini, don’t miss my top 5 island hopping trips from Santorini.

EXPLORING OIA

Oia hangs suspended above the Aegean Sea, about 130m / 430ft or so from Ammoudi bay overlooking the islands of Thirasia and Palia and Nea Kameni. Fira and Imerovigli are also visible across the caldera; Oia is built at a lower altitude than both of them (Fira is built at an average altitude of 250m / 820ft and Imerovigli at approx. 350m / 1150ft) which makes the views on this side of the island less dizzying yet still incomparable.

Oia’s strategic location right at the north tip of the crescent also allows for vistas of the open sea in the northwest. Moreover, it made the village into an ideal location for viewing Santorini’s legendary sunset (more on that below)!

A WALK AROUND THE VILLAGE

Spending a morning, afternoon, day or week exploring the cobblestone alleys of Oia makes for the trip of a lifetime. Everywhere you turn, there are charming windmills, chapels, cave houses and domed churches, a true celebration of traditional Cycladic architecture with a Santorini twist. Building cave houses deep into the volcanic rock perfected the construction of vaults and arches which have been used extensively in lieu of the classic Cycladic flat roof. Furthermore, for every 50 or so classic whitewashed houses, there will be one painted in a beautiful bright colour, a beacon of playfulness in the gleaming sea of white and blue.

In Oia, every single house, no matter how modest or small, has somehow managed to have a sitting area in a terrace, roof or balcony overlooking the caldera! Nevertheless, in the 19th century, during the peak of Oia’s prosperity (excluding the last 20 years that is), the ‘posh’ neighbourhood was Sideras, the inland part of the village, where the grand, two-story captains’ houses were located. Many still survive to this day. In fact, one of them hosts the Maritime Museum, a hidden gem for those interested in the long history of Oia and a haven from the busy streets of the village!

While walking around Oia, you will find a variety of cafés, restaurants and boutiques so there will be plenty of opportunities for a refreshment, traditional meal, elegant dining as well as a cute, high quality souvenir or some designer shopping! For those who enjoy visiting unique bookshops around the world, Atlantis Books carries a big selection of carefully curated books in its rustic wooden bookshelves. The charming bookstore even features a sea facing terrace where it hosts its sunset readings…

THREE DINING RECOMMENDATIONS FOR THE TOWN OF OIA

There is a variety of restaurants in Oia, so my list of recommendations is by no means exhaustive! I will only mention three places that we visited and enjoyed, just in case you are in need of a recommendation.

Skala restaurant serves Greek / Mediterranean cuisine and features a terrace with a view over the caldera and a nice courtyard. I am Greek, so when a restaurant executes well-known classic recipes to perfection, like Skala did, it definitely gets a seal of approval from me.

For a more gastronomic take on Greek / Mediterranean cuisine, head to Red Bicycle. Its stylish terrace overlooks the caldera and the rest of Oia, including some of its beautiful blue-domed churches. Our dinner was not just tasty but very romantic too, so that’s two thumbs up from me!

Last but not least, the delightful courtyard of Karma is a little bohemian oasis of calm, just off of the main street. Even without the sea views, the ambience is charming and the Mediterranean dishes were tasty and reasonably priced too. All in all, this is a great choice for a relaxed brunch, lunch or dinner.

Needless to say, given how busy Oia is during the summer months, it’s always worth making restaurant reservations, especially during peak times and even more so if you wish for a table with a view. In some cases, a minimum spend might be required during sunset time.

ALL PHOTOS: RED BICYCLE RESTAURANT

HAVING LUNCH OR DINNER AT AMMOUDI BAY

I feel like Ammoudi bay is the kind of place that some people absolutely adore while others do not really get what the fuss is all about. Personally, I understand and partially agree with both sides!

Ammoudi is a lovely little restaurant-lined port where people have fresh fish while gazing at traditional caiques merrily bobbing on the beautiful blue water. Charming, right? Yes, but, if these are not your first couple of days in Greece you’ll know that there are hundreds of places as idyllic such as this. While the charm of having lunch or dinner next to the water never gets old, I think that for some people who are used to this sort of scenery, visiting Ammoudi may be more trouble than it’s worth. Here’s why that might be.

GETTING TO AMMOUDI

Firstly, access can be a bit of an issue.

To get to Ammoudi bay from Oia, you will have to go down (and then, up) about 300 steps. That is more than a 10-storey building! Also, these are old school steps; they are shallow, uneven and sloping, hence inherently more tiring. They are also made out of cobblestone, so they can feel a bit slippery under the soles of sandals or flip flops.

My fiancé and I did both the pre-lunch descent and subsequent post-lunch climb. Needless to say, it was pretty darn tiring! I would not recommend it to anyone not confident on their ability and willingness to see it through. Oh and those donkeys that you see in the photos? I am sure you’d agree that we should just let them be. They are too cute to be carrying us around! That’s why we invented cars! Speaking of, you can also reach Ammoudi by car but opt for a taxi as parking spaces are a rare find.

ABOUT AMMOUDI RESTAURANTS

Two more reasons why Ammoudi is not everyone’s cup of tea are restaurant prices and the fact that it is very busy, especially at peak times.

We visited Sunset restaurant on a hot summer’s afternoon. As we were having too much fun going down all those steps to Ammoudi, we arrived quite late for lunch. Luckily, this granted us a front row table! Adding to this the good quality food and classic dishes, I must say we definitely enjoyed everything about that lunch. However, we did feel that a similar experience anywhere else in the coastline of Greece would have cost much less (and I think that’s true for all restaurants in Ammoudi). Typical Santorini, you’d say.

Well… yes and no. I am Greek and I have also travelled quite a bit. In my humble opinion, nothing compares to the view of the caldera from the dizzying heights of Oia, Fira or Imerovigli. However, when it comes to Ammoudi, as lovely as it is, I don’t feel it’s that unique, especially when it comes to the sea views. So, if you are dubious about getting there, the prices or you just don’t have much time in Oia, you could just skip Ammoudi.

On the other hand, the view from Ammoudi looking back up to Oia and the red cliffs is pretty cool. Ammoudi also provides a different (sea level) view point for Santorini’s famous sunset and an opportunity to admire it while tucking into some freshly caught fish. So, if this is your once in a lifetime trip to Greece and you don’t mind the steps, taxi or splurging a bit more on a nice meal on the water’s edge, don’t overthink it. Go to Ammoudi, open a bottle of crisp Santorini white and enjoy!

WINE TASTING AT DOMAINE SIGALAS

Winemaking is probably one of the two words that springs to mind with every discussion about Santorini, the other one being volcano! Indeed, the tradition of wine production can be traced almost as far back as the beginning of the island’s recorded history. The volcanic soil and Mediterranean climate combined with the local know-how have enabled the production of some very special wines that any oenophile should try!

Santorini is home to many established wineries but the majority of them are located towards the south of the island (check out my list of top 7 things to do in Santorini for more info). The only exception to this is Domaine Sigalas*, a winery worth visiting no matter where you are based on the island, but even more so if you are visiting / staying in Oia (it’s only a 10min drive from Oia to the winery).

*In case you were wondering, I’ll clarify that I have no affiliation with Domaine Sigalas.

OUR VISIT TO THE WINERY OF DOMAINE SIGALAS

During our last visit to Santorini, my fiancé and I visited Domaine Sigalas and had a delightful wine tasting session and light dinner. Domaine Sigalas is one of the most prominent exporters of Greek wines worldwide and the winery’s renowned, award-winning labels are also available across Greece.

We visited the winery late on a balmy afternoon and sat on the leafy terrace to try a selection of ten wines and a variety of small plates. Happily, we found pretty much everything we tried to be excellent. Naturally, some wines were more aligned to our personal preferences than others but still, everything was delightful. Apart from the wonderful wine, the service, wine tasting area, shop and, most impressively, the food was excellent too. We also found the pricing to be quite reasonable. Lastly, the whole experience was relaxing, casual and calm. The vineyard surrounds the seating area, so it’s really quiet and green. I also think that the lack of a caldera view made everyone to focus on the wine rather than taking photos relentlessly!

All in all, if you are not after the signature caldera views (which other vineyards do offer), I highly recommend visiting the winery of Domaine Sigalas near Oia. Our visit and wine testing session there proved to be quite a relaxing and authentic way of tasting some of Santorini’s most wonderful (and award-winning) wines. I should add that Domaine Sigalas also offer guided tours of the vineyards which is something I’d love to do another time!

ENJOYING THE SUNSET

While in Oia, you can enjoy the sunset from a fair few restaurants and bars, on the street, next to the cliffs, from Ammoudi bay and even from a sailing boat. It all comes down to your levels of preparation, patience or luck! Booking a table at a restaurant or bar (or a sunset cruise) is probably the most expensive but stress-free option to see the sunset. Alternatively, head for any west facing view point looking out into the sea about an hour or so before sunset!

NAVIGATING THE STREETS OF OIA AT SUNSET

Amongst the best spots to view the sunset (if not the best) is the Castle of Oia, the ruins of a Venetian castle located right at the northwestern tip of the island. At that point, one can view both the caldera and the open sea and witness the scenic spectacle of a Santorini sunset. Needless to say, this is the hardest place to get a spot for viewing the sunset.

The castle of Oia is not the only place filled with people at sunset. Throughout Oia, all the streets overlooking the sea are inundated by people standing or sitting on anything that remotely resembles a ledge. Naturally there are many people who watch the whole thing through their phones… Personally, I liked those cool cats who did so with a glass of wine or champagne at hand or even a guitar!

I don’t like busy streets but what you’ll see in Oia at sunset time transcends that description. People from all nationalities gather around the quaint alleys and come together to experience this amazing moment in time. There’s a real buzz, it’s almost spiritual! It’s also very crowded. All things considered, even if you don’t find the perfect spot to view the sunset, you will still have experienced something unique just by being there. Watching the sunset in Oia is a celebration and, as such, it can be rewarding and fun but also a tiring logistical nightmare!

… AND A SECRET SUNSET SPOT

During our last trip to Santorini, we got incredibly lucky during our walk around town and found a little spot that not many people seem to know about which is perfect to view the sunset in a relaxed way. This is a little jewellery and crafts shop called Glitzy Windmill (it’s on Google maps). The shop features two lovely terraces overlooking the sea and if you pop by around sunset time you can get a glass of wine or beverage along with a piece of jewellery for about 15€ per person. Then, you can enjoy the sunset from the shop’s terrace, away from the crowds!

IS VIEWING SUNSET IN OIA TRULY WORTH THE EFFORT?

Neither my fiancé nor I are big on sunset watching. When we decided to chase the sunset in one of our evenings in Oia, we didn’t stress about getting the perfect spot so we found mingling with the people on the streets 60% celebratory and 40% challenging… Anyway, it was only by accident, as we were about to give up, that we ended up with two spots in Glitzy Windmill and were able to view the sunset properly.

When there is a lot of people trying to do the same thing, being in a relaxed mood and an accepting mindset is key. I think that’s important for enjoying sunset in Oia too! Staying in Oia for multiple nights will also help ease off the pressure. So, unless you are happy with spending something extra and booking a table with a view or a sunset cruise, don’t plan your one and only visit to Oia around sunset. In my opinion, the village is at its prettiest when the sun is high in the sky since the colours of the houses, the burnt soil and the sea are at their most vivid! In the height of summer, the village is magically peaceful early in the morning, so, I’d personally plan my visit around that.

Nevertheless, die hard sunset lovers will be glad to know that the sunset that we did sit down and watch from start to finish was beautiful and definitely worth it. I would put it in a 5th place after sunsets I have seen in Gilli Air and Bali in Indonesia, Hawai, and Isla Holbox, Mexico. That’s some stiff competition!

FINAL THOUGHTS: HOW TO SPEND ONE PERFECT DAY IN OIA

Oia is the kind of place that you can see in a whirlwind of a day or enjoy for longer, taking it slow and keep exploring its magical nooks and crannies. Having said that, I believe that most travellers, by necessity or choice, may only have one day or so in Oia. Luckily, you can experience everything I mentioned in this blog post in one very full but fulfilling day!

For that one perfect day in Oia, I’d recommend spending the morning exploring the village and the afternoon in Domaine Sigalas (where you can also have a light meal if you wish). For a proper lunch / dinner, head to Ammoudi or one of the restaurants in town, depending on where you wish to see the sunset from… Make your reservations for dinner and wine tasting ahead of time, wear comfortable shoes and you are all set for the loveliest of days! Enjoy!


This is not a sponsored post & I am not affiliated with any of the hotels, restaurants or organisations mentioned.


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2 Comments

  1. Chryssa
    July 15, 2023 / 6:25 am

    Lovely article,very informative!

    • Georgia
      Author
      July 17, 2023 / 10:48 am

      Thank you so much!

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