This post contains affiliate links. This means if you use my links and make a purchase, I will earn a small commission, at no extra cost to you. You’ve seen everyone travel to Santorini. You’ve seen the stark white rooms, the hot tubs on balconies, and the sunset over the cliffs of Oia. You’ve heard mixed reviews, because some people say it’s so overrated and some say it’s the most amazing place they’ve ever been. I’m here to say that there’s something for everyone at any destination – and even the most touristy destinations can have some hidden gems. While some people want that dreamy, white building, blue roof, picture-perfect Santorini vacation, others want to go to the small beach towns and the less inhabited side of the island. I’m here to say that you can do both, and you can explore the history of the island and some spectacular views that aren’t totally overrun with tourists. With 2 full days in Santorini, here’s what we found: Night of Arrival: We arrived at almost midnight to the Santorini aiport, coming in from a late flight from London. A tiny airport, we made our way into the small arrivals area where we went to one of the few car rental kiosks and picked up our rental car for the duration of our time there. If you follow this itinerary, and if you want to go to multiple different areas of the island, definitely rent a car (or ATV!). And if you arrive late, make sure to rent a car from one of the car rental companies that stay open late enough! Night of Arrival Hotel – Olympic Hotel I cannot recommend this hotel enough. It was around 5 minutes from the airport, so it wasn’t difficult to get there in the dark in a new country, and it was pretty cheap for Santorini. While we decided to just choose a cheap yet nice option for our late arrival and our one night staying there, I think it is a great hotel for your stay. It is in the middle of the island, so there are great views of the ocean, and it has a complimentary breakfast and a pool. This is a great option for the money-conscious! Day 1 – Off the Beaten Path & Winery We started our day off early, waking up to the sunrise over the sea. It was bright orange, and it easily got me out of my bed and ready to finally see the island in the daylight. We got dressed and made our way down for our complimentary breakfast. (Let’s be honest – there’s little I love more about a complimentary breakfast – or breakfast at all). There was a nice array of food, and we sat outside on the cute patio while talking about our excitement for the day ahead. STOP 1 – VIEWPOINTS: The Heart of Santorini & Santorini Caldera – Southern Panorama View You should directly search those names on Google Maps to make it easiest to just add them to your route. The Heart of Santorini was our first stop, and I’m so glad it was. There was maybe one other couple there when we first pulled up, but they quickly left, and then it was just us exploring the viewpoint since there were multiple different views all at that one spot. The next spot was Santorini Caldera – Southern Panorama View. This spot is pretty much the same as The Heart of Santorini, but it is just less stuff going on and has more of a raw view of the cliffs where the wind just hits you as you look across at the caldera. Note: when you hear the word caldera in Santorini, it means the small island you can see in the distance when looking off the west side of the island. It is the remains of a volcanic eruption, and the caldera view is typically the more sought after places to stay! STOP 2 – AKROTIRI LIGHTHOUSE This stop is situated on the western-most tip on the south side of the island. There was no one else there when we got there, and we were able to explore around the lighthouse and see the clear blue water from very high up and just generally take in a different type of view than we had seen before. STOP 3 – RED BEACH While this is definitely far from “off the beaten path,” it fits in this category, because this itinerary covers the rest of the south side of the island, so it makes sense to visit this beach while you are down there! Just a quick drive over there (the earlier the better!) you can probably find a pretty close parking spot, and just a fair warning – it is a bit of a treacherous hike. We passed some vendors selling souvenirs, people selling food, and a musician singing along the little path. After that, there are ropes and a pretty rocky and sloping hike down to the actual sand, but it is worth it – especially if that is going to be your first chance to put your feet into the clearest blue water of the Mediterranean Sea. While it was a little too cold, and there was a little too much shade on the beach for our liking, plenty of people were setting up for a day of hanging out there, so spend as much time as you like! STOP 4 – AKROTIRI (hopefully YOU get to go!) This looked like an amazing stop to make, especially if you are intrigued by history. The sad part is that we weren’t sure where to park since a lot of spots were full and it looked like a more popular spot to visit. Essentially, Akrotiri consists of prehistoric remains of a city that has been excavated. It got covered in volcanic ash, but the area is now covered and available for tours so you can walk around the area and get an idea of what it used to be. Let me know if you are able to see this spot! STOP 5 – BLACK SAND BEACH at PERISSA Driving over to the eastern side of the island next, you will find a quaint beach town called Perissa. Filled with cute hotels, quaint food spots, and a different vibe than Oia, Perissa would be a great place to stay if you want to be at Santorini but away from the major tourist hub of Oia. We made our way over to this area, and walked around a little bit before stepping onto the black sand beach and dipping our toes in the water for a little bit. If you want to make this a nice afternoon spot, you could easily throw on a swimsuit, grab a drink, and relax on the beach for a little bit! STOP 6 – HOLY MONASTERY of PROPHET ELIAS & PYRGOS I combine these two stops, because you have to drive through Pyrgos to get to the Monastery. Prygos is a vibrant little town in the middle of the island on top of a massive hill. It is home to a picturesque white church with a blue top, and it has many places to eat and walk around. You can even see both sides of the island from up there! Moving further up the mountain, you get even more views of the Mediterranean Sea on both sides, and you will drive up to the Holy Monastery of Prophet Elias. While there was a wedding while we were up there, we were still able to walk around and see the different old buildings that make up the monastery and walk around the property a little bit. STOP 7 – ANCIENT THERA Oh, man. This stop is a bit treacherous, just to warn you. To get up here, you have to drive up an almost fake-looking driveway that curves up and around multiple times. While going up, there is a stop where you can actually get out and hike a little bit to see some other remains and see the road you drove up from a distance. When you get up there, you can walk around and see more ancient ruins and read about them – not to mention get multiple views from this massive mountain that look unlike any of the typical pictures of Santorini. NIGHT 1 – CALDERA VIEW (food) and SANTO WINES WINERY After all these stops were said and done it was well into the afternoon, so we were now ready to make our way to our hotel, which was located on the southern side of the island. But first, food. On our drive that morning, we had scouted out some potential options, but we opted for eating at Caldera View, which has exactly what you would think – a perfect view looking out over the cliffs on the caldera side. We had delicious food – some more Greek than others, and then we headed out to our hotel. Now, for the whole trip in Greece, we decided to save our money and not stay at the most expensive places, because we knew we wouldn’t be spending much time there anyway. In Santorini, we wanted to splurge and get a really nice place that looked like what you would expect when seeing pictures. I really cannot recommend this place enough – Kalestesia Suites. While it has the white buildings with the hot tubs on the balcony and the view of the caldera, it was on the south side, so we got the best of both worlds – an amazing accommodation without the tourists. The only downside to this place is the road to get there is extremely narrow and extremely hard to pass through, but we made it and we got settled into our little humble abode that we would get to stay in for 2 nights. We had an upstairs suite, which meant a balcony with a hot tub, a bed on the bottom floor, and a loft with two twin beds and a balcony off the loft as well. We spent the afternoon lounging in the sun on our balcony and reading (there is a pool, but it was closed because the wind conditions were so crazy when we were there!). When it was evening, we decided to make our way back out close to Fira and go to Santo Wines Winery. One of the top recommendations when looking at Santorini is to go to a winery, and this one did not disappoint! Situated right at the side of the cliffs, we got a table looking out at the caldera, and we tasted 10 different wines, while getting to read about each wine and enjoy the sunset. That night, we wanted to watch the rest of the sunset from our hotel, so we quickly made our way back, and we sat on the edge of the hot tub and watched the sunset make its way down into the sea while looking at the colors change in the sky and the island light up at night. There is no better memory than that feeling. DAY 2 – Catamaran Cruise STOP 1 – Bakery Santa Irina Our hotel offered breakfast later than we would have to be out for our cruise, so we knew we needed to eat beforehand. We got up bright and early (before sunrise!) and made our way back to Perissa, where we found a bakery that opened super early – Bakery Santa Irina. When we got there, it was only locals, but they were extremely helpful, even telling us what was good there despite the language barrier. The whole store was lined with pastries, but just to let you know, they only take cash! We didn’t have cash, so the owner was kind enough to tell us that we could come back anytime that day and pay for it later. (How good are humans?) STOP 2 – CATAMARAN CRUISE … Continue reading Best of Santorini in 2 Days | Off the Beaten Path Itinerary