How To Spend 48 Hours in Santorini

Updated: Apr 3, 2021


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No trip to Greece is complete without a stop in Santorini. With it’s snowy white, hill stacked yposkafa (cave buildings and houses), it’s postcard perfect in every way. Whether you want to relax on a beach, go on a vineyard tour in the countryside, hike the cliffs or spend the day sailing, there is something in Santorini for everyone. I think three days would probably be perfect for you to experience a little bit of everything, but if you’ve read any of my previous posts regarding the legs of our grand adventure, then you know we were on a time crunch and only had two days. But we defintiely made the most of our time and enjoyed just about every second of it.


Getting To Santorini

If you’re coming from Athens you are probably going to catch a quick hour long flight to the island. We were on the first flight out in attempts to maximize our time. My only regret was that I wish I planned for an hour later. While our plane arrived at 6am, the hotel didn’t even have someone come to open until 7:30am. It was pouring and still dark out when we arrived so we had to mosey around this little convenience store for a while to stay dry. Luckily the rain died down and we were able to find a little spot to sit to watch the sunrise, complete with a gorgeous full rainbow in the caldera.

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While it was a little stressful, given how tired we were and just kind of thrown out of the loop of everything I had planned (welcome to travel) that gorgeous calm that happened after the storm turned the morning mood around.

So, my word of advice to you is don’t bother getting into Santorini earlier than 7am, it may seem like a good idea so you have more time on the island, but just go ahead and enjoy the extra hour of sleep. Granted this could have been because we travelled during off season, but still.

Where To Stay

Santorini is essentially categorized into three different parts that you could, or would want to stay in. You could of course stay in the countryside, but if you’re coming to Santorini for the cliffside experience then you’ll want to stay in either Oia (the main tourist part), Fira (the oldest part), or Imerovigli (the best part). I say that Imerovigli is the best part of Santorini to stay in because, well, it is. You are in between Fira and Oia, you have the classic stacked white cave house look no matter where you stay, you’re looking out to the caldera, but you don’t have heards of tourists marching outside your door at all hours. I couldn’t have been more happy with our decision. 

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Regardless of where you decide to stay, there is no shortage of incredibly gorgeous bed and breakfast boutiques. Depending on your budget, you could have an infinity swim out room like the ones at Pegasus Suits and Spa (where we were going to stay but decided to extend our vacation longer and stay in a cheaper place). Or if you simply need a place to rest your head, you can get reasonable accomodations that will still more than likely have a delicious breakfast and a beautiful view.

We chose the midrange option and stayed at the Hotel Sunny Villa. Besides the communication issue surriouding our ride from the airport to the hotel, the staff was very friendly and welcoming. Due to their mixuo, they even let us choose the room we wanted to stay in that was available. We got this gorgeous corner honeymoon suit with a private jacuzzi. I loved that it was a corner suite because the other rooms we looked at were less private, so if there is any way you could request that room I’d recommend it a million times. On our last night we got gyros to go and ate them in the jacuzzi while watching the sunset. It was definitely a highlight of the whole trip. Not to mention the breakfast that they brought to the room daily was to die for. Greek yogurt will never be the same when not consumed in Greece. I miss it every day.

Overall I’d recommend staying at this hotel. The price is very fair for what you get and it’s much quieter than some of the other hotels we looked at in terms of foot traffic. 

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What To Do

And real quick, what not to do: please, please, do not ride the donkeys. They are not treated well and are worked far harder than any working horse should be. If you cannot make it down the steep walkways and up again on your own, please just stay up in the main area.


Hike the Cliffside Around the Caldera

There are a couple of ways to do this depending on time, and fitness level. Of course, my suggestions will be based on if you are staying in Imerovigli. Obiously if you’re staying in either Fira or Oia you can just hike from one side to the other. It’d take probably 5 hours or so depending on how quick you were. We took our time.

1. You could hike to Fira and then hike back through Imerovigli to Oia

2. You could catch a bus to Fira and then hike through Imerovigli to Oia

3. You could just hike to one side one day and the other another day

4. We skipped Fira and just hiked to Oia. It took 3 hours, but we stopped along the way for photos and at a couple cafes for drinks. 

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Regardless of how long you invest in this, it’s totally worth a go. Along the way we came across gorgeous churches, friendly fellow hikers, adorable local wandering guide dogs, and stunning views of the island. Some parts are easierr than others, but if you’re in even remotely good health you can manage it. I have a bum knee so coming down the sandy stones was difficult for me, but other than that it was great. It’s tiring for sure, but when you arrive in your destination of choice, find yourself a restaurant and grab a cold beer and a hefty meal for a job well done. 

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After we refuled we explored around Oia for a while, but it was far too crowded to actually enjoy much of it since we arrived around mid day. We explored Oia as much as we could take,  considering we were tired from the hike, before catching a bus back to Imerovigli. 


Sunset boat tour

This was the only planned excursion we did in all of Greece and it was amazing! We went out on a catamaran with 7 other couples and the crew. They took us to two different swimming spots around the Caldera before we sat down and to a dinner that the crew cooked. It was delicious! And did I mention it was unlimited wine and beer (and of course regular drinks). We met some really great people on that cruise, so much so that I wish we had asked for their contact info and been able to stay in touch. 

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A lot of the tours offer a day time and a sunset cruise. I can’t stress this enough, go for the sunset cruise. While everyone is making their way to Oia to be crammed against one another, you’ll be sitting pretty on the edge of a catamaran in the middle of the Caldera, wine in your hand, watching that same famous red sunset. It’s incredible. 

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Book a tour:

Morning or Sunset Cruise with Food & Drinks

The Santorini Catamaran Red Cruise with Meal & Drinks


Vineyard Wine Tasting

This is where I say three days would be perfect. Day 1: explore around the part of the island you’re staying on. Go on a gorgeous sunset boat tour. Day 2: Hike the cliffside and explore the other main parts of the island. Day 3: Get into the countryside and go on a wine tasting. Wine is huge in Santorini. It’s one of the things I’m sad we didn’t have time to do. But one of the reason why we’ll be going back at some point.


Book a tour:

Santorini: 4-Hour Sunset Wine Tour

Santorini: 4-Hour Small Group Wine Tasting Tour

Santorini: Sunset and Wine Tasting Tour by Electric Bike


Where To Eat

There is no shortage of good food around Santorini. We didn’t get to eat at as many places as I had hoped but the ones we did check out were great.

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This is the restaurant we went to after our hike so we splurged a bit and every bite was incredible.

We started with some pita and Tzatziki to calm our rumbling stomaches. 

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Of course, to feel a little healthy, we the Santorinian salad (greek salad, essentially). A bowl filled with lucious tomatoes, olives, cucumbers and onions tossed in an olive oil and spice dressing and topped with a huge slab of feta cheese, also covered in the dressing. It was the best greek salad I’ve ever had. And so refreshing after our long day.

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Next we got the Spetzofai, which is spicy stewed sausage with peppers, tomato and cheese. You can get it alone or in a loaf of bread. Obviously we went with the loaf of bread. I highly recomment, even if you’re not much of a bread eater.

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Finally, we got the “minced meat cooked with vegetables and graviera cheese.” It was probably our least favorite of the dishes, but probably only because we were getting full at that point. The baked cheese on top and the sauce the meat and veggies were cooked in was delicious.

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Obviously, we had to be rolled out at the end of our feast, Violet Beauregarde style. Do I still wish we got dessert even though we couldn’t possibly fit it in? Yes. Next time. 


Confetti - Imerovigli

This little haven was just what we needed after checking into our hotel on the first morning. Their greek yogurt with honey, almond, granola and blueberries was to die for. 

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We ended up coming back in the afternoon on our second day to try out their gelato and it was just as yummy! The decor is also super cute too!


Let's Eat - Imerovigli

A great little souvlaki place close to our hotel. This is where we grabbed gyros to go and ate them in our jacuzzi.

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But we also enjoyed dining on their patio on our first day in Santorini with a table full of yummy souvlaki.

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I hope this little itinerary helps inspire your first (or next!) trip to Santorini.

Looking for more Greece suggestions? I've added some posts below for you to peruse.


If you take any of my suggestions please let me know. Or if you have your own I’d love to hear your experiences in the comments!


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Prost,

Emily