Santorini travel guide – Oia, Greece (where to stay – what to do)

I’ve dreamed of visiting Santorini since I was a little girl. Santorini is one of the Cyclades islands that requires no introduction. It’s that magical, picturesque spot that you see everywhere on Pinterest and Instagram. Think of Santorini as the supermodel of all the Greek islands. It’s no surprise that it is one of the most popular islands in the world

It’s most famous for its world renown sunsets, multicolored cliffs, whitewashed houses carved into the clifftops and blue-domed churches overlooking the caldera. It also has unique beaches with black, red, and white sand all on the same island. My friend and I traveled to Greece and we spent 6 days in Santorini and opted to in Oia. Outside of Oia you can drive, but other than that—it is a pedestrian-only little town. Make sure to wear very comfy sandals and prepare to make your way on foot. Be mindful of the extremely steep and slippery steps!

A little bit of history

Santorini has a lot of interesting history. It experienced a devastating volcanic eruption – the largest recorded in history, dating back to the 16th century BC. As a result of the explosion, the island sank, and the rest of the island got heavily damaged. What’s left today is a croissant shaped island, previously round, featuring jaw dropping cliffs. (Santorini is basically a group of islands remaining.) Greece is not without its tragedies, both historical and present.

^^Photo by: @ammoudie_santorini since you need a drone to get a high up view like this.


Santorini attracts more than 2 million tourists a year, and it’s fair to state that it is not the most budget friendly destination. We flew from Canada, and if you are flying from somewhere not in Europe, plan to spend $1000-$2000 on your flights. Of course, depending on what time of year you travel, you can save money. Bear in mind that Santorini is a tourist island, and like many Greek islands, they shut down during off their off-season. We visited at the tail end of the season (end of sept/early oct) and we got there a week before island closures. We were extremely lucky because we got hot summer weather the entire allowing us to swim and it felt like mid-summer. It truly could have gone either way. We also got to experience “less tourists” than usual. Even then though, the amount of people was still overwhelming at times.


Due to its popularity, the price for accommodations can be around twice as much as what you would pay in Athens or elsewhere. You can expect to pay at least around $200-$250 dollars a night. The island basically has two different sides with many towns to stay in, so you need to pay attention which one you choose. You will have the option of luxury, mid-range, and budget-“ish”. The first thing you need to decide is how important it is for you to stay in Oia — which is the beautiful town you see in photos of all over the internet and the photos on this post. Hotels in Oia will be more expensive than those outside of it (more luxe)—and rooms tend to be on the smaller side—but if you have the budget, I think it’s worth the splurge. We stayed in Oia, and the views are unlike anything you will experience in your life. It’s also worth noting that since the hotels are gorgeous, and most have infinity pools, you’ll probably spend a lot of time at the hotel relaxing, which in my mind is money well spent. We spent a lot of time in our cave hotel taking in the views. We opted to splurge for 2 nights and upgraded to a honey moon suite to get our own private pool/hottub. It felt like our own private oasis away from all the tourists. We knew that this was a once in a lifetime girls trip and we had planned accordingly. If you’re staying out of town or outside of Oia and just coming in for sunset, it’ll be much more difficult to experience the beauty of it all, but it is still feasible if you don’t mind tourists. A lot of travelers also opt to stay in Fira ( the capital – mid range prices) which is nearby and still has a lot of charm. The beach towns (budget) are situated on the eastern part of the island and if you’re looking for saving some money, it can be a great choice to stay at one of them. I was told that the most popular beach towns are Kamari and Perissa.

Things to do

Watch the sunset:  Santorini’s sunsets are iconic — listed as a “must do” on almost every travel guide. And I would have to agree — they are indeed as magical as they say.

Go on a Boat or Catamaran tour: You have ton of options to go for a tour, whether it be a popular sunset tour, visiting nearby islands and beaches, or visiting the volcano.  

Hike the Caldera: These are steps that go from the top of Oia all the way to the bottom (approximately 300 steep steps). It might not look like much but trust me, it’s a little workout. They also offer the option to go down (or up) by donkey or lift). please don’t opt for the donkeys and WALK – these poor animals!) The walk is still feasible and it’s worth it. I think you can also rent a cab if mobility is an issue.

Walking by the donkeys on foot

Ammoudi: When you hike down you end up at Ammoudi beach on the water. It’s crazy beautiful and you can have the freshest seafood at one of their restaurants. I highly recommend eating at the Fish Tavern and having a drink at sunset at any of the restaurants. The food in Santorini is very good.

Hike from Fira to Oia (or Oia to Fira): This is a stunning 10 km hike that is well worth it. Make sure to leave early in the am to avoid the scorching hot sun. It will take about 2-4 hours to finish the hike depending on your physical condition.

Visit the volcano and Hot Springs: Many boat tours allow you to swim in the pretty waters of the caldera. If you have never tried it, this is the right opportunity.

Rent ATV’s: I know that renting an ATV in Santorini looks really cool, but it can be very dangerous if you don’t have any experience and you can easily hurt yourself. If you do this, make sure that you’re experienced. If not, best to cab around (very affordable). In Santorini, the roads connecting the villages are poorly lit and the strong wind could be a problem (this is a windy island).

Go to the beach: Most of the beaches on Santorini are in the south part of the island. The most important seaside resorts are Kamari, Perissa, Perivolos and Akrotiri. Santorini is not famous for its beaches, in fact, it’s nothing to write home about considering the beaches that Greece has to offer. However, it’s still worth visiting when you are there and the sand colours are unique.

What you won’t see on Instagram

There is absolutely no doubt that Santorini is picturesque, but there are things worth noting that make it not so #wanderlust that you should be aware of before booking your flights.

Tourists: The number of tourists is truly overwhelming. As mentioned, over 2 million tourists flock to Santorini every year. You will be doing yourself a favor preparing for this and being patient. Around sunset time, you’ll see thousands of people bum-rushing the area of the caldera for the best views for sunsets and the walking paths are always extremely crowded. If you want to avoid the chaos, go have drinks at a rooftop (like Catch) that offers a straight-on view of the sunset. While our accommodations were expensive, it allowed us to enjoy our private sunset views without the overwhelming tourists trying to get an Instagram worthy shot. This is where staying in Oia pays off.

Santorini’s animals: The darker side to paradise. there are many, many stray dogs, and cats in Santorini. When we first got there, I thought the dogs belonged to somebody because a lot of them had collars, however these are mostly all abandoned animals that fend for themselves. Seeing these animals travel from one side of the island to another looking for companionship, food and water was extremely heartbreaking and will forever be ingrained in my heart. I wish I could have brought them all back home with me. Being the animal lover that i am, it really broke my heart. Luckily, a wonderful local named Christina Kaloudi started an organization and devoted her life to the Santorini Animal Welfare Association (SAWA). However, while this is an incredible accomplishment, it’s still not enough. What can you do? If you visit Santorini, please donate to an organization, be kind to the animals in need, and please do NOT use the donkeys as a means of transportation for yourself or your luggage.

Closing thoughts

Despite Santorini being a small island, there are still many things to do and places to see. Three or four days might be enough to visit the island, however, if you want to enjoy its unique atmosphere to the full, I suggest that you see as much as you can and take part in all the experiences. If you have more than a week, you can also visit nearby islands.

I hope this guide was helpful and that you have an amazing trip to remember.

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