I had been wanting to visit Santorini ever since I saw a picture of one of those dreamy cave pools, but every time I checked for flights, the prices were crazy high (I’m talking +500€ from Spain!). So I’d always put Greece aside and ended up choosing another destination. However, this year I was able to find flights for 60€ with return!! (As always, I use Skyscanner to find the best deals). So it finally happened, in the middle of a pandemic, we decided to go to celebrate my birthday. So here’s my guide on what to do in Santorini in 4 days!

• How to get to Santorini: there are many European cities that run direct flights to and from Santorini. Otherwise you can fly to Athens (the capital of Greece) and from there it’s a short flight. I recommend using Skyscanner to check the best offers on flights. If you are already in a nearby island (or want to visit afterwards!) there are very convenient ferries at FerryHopper.

• Best time to visit Santorini: avoid July & August, as Greece and specially Santorini is a very popular destination. We visited Santorini mid-September, but if you can, I recommend going at the end of September or beginning of October. For us, the weather was so hot it wasn’t nice being out during the day; and accommodations still had midseason prices.

• Where to stay in Santorini: check this other article if you want to know the best hotels in Santorini with private pool and views.

• How to move around Santorini: I highly recommend renting an ATV if you feel confident. Driving is really easy as there’s only 2 main roads; parking was available at most places and this way you can visit other towns instead of just staying in Oia. Taxis are not always available and very expensive.

• How many days to spend in Santorini: it’s a very small island so 3-4 full days should be enough. We spent 3 nights and I’d say we could have spent one more night but that’s it. We are quite chilled and we only went out in the early mornings or late afternoons; so probably you could see everything in 3 days. If you have more time I’d recommend visiting another island like Milos!

Our 4 day trip to Santorini

My general recommendation would be to wake up early, explore before it gets too hot, then stay at the hotel during the hottest hours of the day, and go back out for sunset and dinner.

There are many restaurants all over Santorini and we tried a few and they are all amazing!! Seriously, greek food is out of this world. I recommend trying local cuisine and specially restaurants that source their ingredients locally as well.

Day 1: arrive and settle down

We landed in Santorini around 5pm, and we had booked our first accommodation for that night in Oia. The airport in Santorini is really small (basically just one room); so the transit was very smooth and quick and we were out of the airport in 5 minutes. Hotels charge 40-50€ for one way transfers, so we decided to rent an ATV. The prices for ATVs are 30-40€ per day so it made sense. They allow for some luggage in the back, and since we only travel with backpacks it fitted perfectly.

As we got outside, we found that there’s absolutely no ATV rental companies at the airport (only car rentals); and we hadn’t booked in advance so we ended up kind of stranded there! We walked to a nearby coffee shop where the waiter called a friend of his that rents ATVs but after 30 minutes he still hand’t arrived so we just decided to leave. After calling a nearby company and making sure they had availability, we grabbed a taxi to get there (stupid idea, as we paid 15€ for a 5 minute ride). Just be smarter than us and book your vehicle rent in advance.

There’s two roads that run through the island, one is on the Caldera side and the other one next to the coast. I recommend driving the Caldera road because it’s much more scenic and you’ll drive up to the top of the mountain! It’s really cool.

The drive to Oia took 20 minutes. Once we arrived the first thing we did was get some gyros as we were starving! If you’ve never tried gyros, they are the most delicious thing (kinda like a kebab but greek); and you should try them asap! We were on a mission to try all the gyros of the island and find the best one lol! The first one we tried was Niko’s Place, and would give it 7/10. Price was 3,50€.

After that we checked in at our first accommodation, Marble Sun Villa, and headed out to watch sunset. The most popular spot for sunset is the Oia Castle, but it’s always very crowded. We walked down the stairs for a bit and to the left there’s a small path were you can sit and enjoy the sunset completely alone, with the same view. Sunsets in Santorini are said to be some of the best in the worlds, so make sure to not miss any!

Once the sun was gone, we walked through town a little bit and went for dinner at Pelekanos.

Day 2: explore Oia

On our second day in Santorini we set to explore Oia in the early morning. It’s a very small town so you can walk around and see everything in 3 or 4 hours. The house we rented, Marble Sun Villa, was perfectly located below the famous blue domes so we could take pictures there at sunrise before anyone else arrived.

We got a little lazy and arrived 30 minutes late and there were already some other people there. That definitely surprised us! We are used to wake up early and being totally alone in most places.

Later, we went to some other popular locations such as Kastro House. We just walked and explored around town and it was really nice. It wasn’t very hot yet and there weren’t many people so we pretty much had Santorini all to ourselves; and enjoyed discovering all the little streets.

Get ready for a good workout though, because Oia is very steep. You’ll be walking upstairs and downstairs all the time!

After a while we got back to our house for breakfast and had a little siesta in our terrace (we were exhausted already!). It was getting really hot, so we packed our stuff and headed to Imerovigli where we were going to spend that second night.

After arriving to the second hotel, Dana Villas; they told us our room wouldn’t be ready until later around 3pm so, guess what we did? Go eat more gyros haha. This time we tried Yogi’s Gyros, they had a big queue outside but they were absolutely delicious! Would rate 9/10.

We enjoyed our gyros and did a little walk around town but it was extremely hot. We headed back to the hotel and had a quick swim at the pool before we got our room. My dreams of staying in a room with a cave pool finally became true! It was the best birthday ever.

The rate included a 15 minute massage, so we took advantage of that. We ordered some drinks to room service and spent the rest of the afternoon chilling in our pool. We also stayed for sunset because the view was amazing and the pool was heated so we never wanted to leave!

Eventually after sunset we decided to go for dinner and walked to Argo Restaurant, which is located in Thera. The walk was 15 minutes and it was extremely beautiful. It’s a path with views to the Caldera and when the little towns light up at night it’s just incredible. I was speechless! (the steep & endless stairs might have something to do with that too haha).

Day 3: explore Imerovigli

On our third day in Santorini we got to explore Imerovigli in the morning. It’s a beautiful small town very similar to Oia but without the crazy crowds! It was really hot so we went for a short walk around the area.

We found the iconic blue domed church with the bougainvillea and there was absolutely no one else there! We also wanted to do the hike to Skaros Rock and the Theoskepasti church. Due to the weather we decided to leave it for another time. However I do recommend adding it to your itinerary because it’s beautiful!

There’s a lot of bars and restaurants in the area with amazing views so we also stopped for a fresh fruit juice and an açai bowl. It’s a very beautiful place much more chilled than Oia and with a more local vibe! I loved it and wished we stayed longer in the area.

If you want to do some more sightseeing I would also recommend visiting Mesaria (it’s a nearby town that’s also very scenic little town full of bougainvillea and pretty houses) or using this day to go to the Red Beach, which is only a 30 minutes drive away but it’s very popular because of its uniqueness. There’s also the option of doing a little cruise around the Caldera which your hotel can arrange for you.

[If you followed my stories on instagram, you know we also visited Milos island during this trip. So on this day we actually took a ferry at 3pm to get to Milos, if you want to know more about that trip let me know in the comments and I’ll write a blog post about our days there! After 3 days we came back and arrived to Santorini at 1pm so for this post let’s just pretend we had a full day in Santorini instead right?!]

Since this was our last night in Santorini we decided to go back to Oia and stay in one of the most iconic spots of Santorini: the famous windmill. The historical windmill was renovated and turned into a hotel room by Charisma Suites.

We spent the afternoon at the hotel drinking cocktails and watched sunset from our private jacuzzi. The views from the room terraces are incredible and you have your own private space so it’s unbeatable!

After sunset we went for dinner to Karma. This is a very popular restaurant settled into a little charming garden and food is amazing.

Day 4: last morning in Santorini

And finally our last morning! We had an amazing breakfast in our private terrace with two very friendly cats that I wanted to adopt, one last dip in our jacuzzi, one last morning stroll around Oia and one last gyro before heading to the airport!

The airport in Santorini is really small so if you are like us and don’t need to check-in any luggage; you can arrive 30 minutes before your flight and have enough time. We arranged with our ATV rental company to pick it up from us at the airport.

Early mornings in Santorini are very peaceful and the light is magical so definitely take advantage of your last morning! I would say 3 nights is more than enough to see everything since the island is quite small.

We had very chilled days as we also like to relax when we are on vacation so if you get some FOMO then you can visit the southern part of the island which is also very beautiful. Otherwise definitely do like us and go to Milos.

Let me know in the comments if you have any questions and I’ll answer there.

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