Best of Santorini in 2 Days | Off the Beaten Path Itinerary
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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
Not necessarily a stop, but after eating our mouth-watering pastries for breakfast, we went back to our hotel and changed for our catamaran cruise. We chose an amazing tour that picks you up from your hotel, takes you to 3 different stops on the cruise, feeds you a “BBQ lunch,” and drops you back off at the end of the day. We booked on TripAdvisor, and I highly recommend this tour! You can check it out here: Sailing Catamaran Cruise in Santorini with BBQ, Drinks, and Transfer.
Make sure to check out the different types of cruise tours so that you know what you are getting and that it works out for you. There are all different lengths of tours, different lunch options, pickup vs not getting picked up – so choose one that works best for you. I always go through either TripAdvisor or Viator when booking tours. All you do is search by the city or by the type of activity and it comes up with SO many options to choose from so you can find what’s best for you.
We got picked up just a short walk from our hotel, and after picking up another group of girls, we made our way to the port where all the catamarans were picking up their passengers. You check in at the desk and they give you a color, and once you hear your color you go and board your ship.
The basics of the catamaran cruise: once on board, everyone will sit to listen to the rules, which is basically not to walk on the net at the front while the ship is moving. There is free wine and beer for sale, there are 2 bathrooms located on either side downstairs on the ship, and there will be 3 stops where you can get off and swim if you want.
The 3 stops we made were at the caldera, Red Beach, and a white sand beach. Each stop was picturesque, but we only decided to get off at Red Beach, because we knew we had to jump in to the Mediterranean Sea at least once! After stop 2, we had lunch – which consisted of chicken or pork skewers and a bunch of different Greek sides. It was honestly delicious. Our cruise lasted a total of 5 hours, and then they dropped us back off at our hotel.
Night 2 – Oia
Truth is, we had a full itinerary planned, and if you aren’t as lazy as us, I will share what we had planned down below. But, when we got back, we ended up showering and taking our time getting ready to go back out, because we knew the most important thing was to get to Oia by sunset.
Stops you could make on your way to Oia:
- Thera (or Fira)
- Virgin Mary Orthodox Church – Three Bells of Fira
- Skaros Rock
- Profitis Ilias
- Panagia
- St. Constantine and St. Helen Chapel
- Cape Colombo
- Santorini Brewing Company
When you drive to Oia, it is extremely hard to find parking, so get there as early as possible (if you aren’t staying there). Note: the police were walking around giving parking tickets if you were parked illegally, so just be careful about where you end up! Although you might have to walk pretty far, it is definitely worth it to see this place at sunset (or even sunrise if that’s your preference), so wear comfortable shoes and get there early.
There will be hundreds, if not thousands of people cramming the streets and cramming the walkways that look over the cliffs. Everyone wants that iconic picture, so do you best to take your picture and then relax for the rest of the time and just enjoy the view.
We actually didn’t even end up standing there for too long, because although it was beautiful, we weren’t huge fans of being surrounded by so many tourists. So, quickly we decided to just walk the streets and admire the shops, the restaurants, and the architecture of the homes in that area.
After this, we decided to get out of there before there was any traffic, so we took the scenic route out of Oia, and we remembered that we needed to go back and pay the owner at Bakery Santa Irina. We found an ATM and headed back to Perissa, where the man was very grateful that we remembered. It was way past dinner time and we needed some food, so we headed back towards our hotel, where we had passed a cute place multiple times where we remembered seeing signs for sweets (ice cream!).
If you search “Bakery Gregory” on Google Maps, it will take you to this cute place that is a mix between a cool coffee shop and a cafe. There was coffee, pastries, sweets, ice cream, coffee, and even a bunch of little quick mart type items. This was a great spot to sit and eat at the end of the night, so I would definitely recommend checking it out!
After that, we went back to our hotel and listened to the wind hitting the shutters as we fell asleep, sad to be leaving Santorini the next morning, but excited to be heading to Mykonos the next day.
Day 3: Departure to Mykonos via Ferry
We woke up the next morning and had an amazing, full breakfast provided by the hotel, and enjoyed the views one last time.
We were set to take the ferry to Mykonos (I highly recommend taking a ferry at least once while traveling in Greece!), so we had to drop off our rental car at the airport and find a method of transportation to the ferry. This could cost a little bit of money, but if you are traveling in a group it will be a little cheaper per person or you can find another group of people who need to go there or close to there, and it might make the price a little cheaper as well.
At the ferry port, there are cafes and shops around, so we sat at a cute little outdoor cafe while waiting for the time our ferry arrived. It is a little bit of a hectic process, but we finally made our way onto the ferry, and we were heading off to Mykonos!
If you are interested in knowing more about the entire trip, ferry travel, and general travel in Greece, read more about the whole trip here:
