Santorini - 3 Day Itinerary

We spent three full days in Santorini and felt like it was the perfect amount of time to see everything if you are planning on stopping at one or two more islands on your trip. If you want to really see Santorini you could easily stay here for a full week and explore each different town and area in so much more detail. But if you stick with this itinerary, you'll feel like you saw enough but could always come back again..

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Day 1

We wanted to get an early start for our first day in Santorini. We chose to stay in Imerovigli (more on where to stay in Santorini here) and planned to spend the full day in Oia. We decided to do this on the first day in case we felt like there was more to see on one of the next few days. We debated whether to do the few hour cliff walk from Imerovigli or take a cab but our hotel recommended renting an ATV as a good way to get around the island on our own schedule so we decided to do this. It turned out to be a great way to get around and it was nice to see more of the non-touristy areas in getting from Imerovigli to Oia. Oia is a small town so you don't need too much of a plan to get around. Once you are there you can't really get lost even if you meander down every side street there is. They all seem to wind up back at the main road. 

One of the first places to stop off the main road is for a view of the three blue domes. It will probably be crowded so best to go early in the morning. To get there, first make your way to the main square in town, where you'll see Ekklisia Panagia Platsani, a Greek Orthodox Church. With the church to your right, continue walking straight down the main street until you see a small black hanging sign for Bulgari Alexandros. Right before the Bulgari store, make a left down the small path and keep going straight until you reach a brown door and fork in the path. From here you can't go wrong in choosing left or right. The left side will give a more zoomed out view, whereas the right side will get you closer to the domes. We tried both sides to get a few different views.


I loved pretty much every view in this area. Literally every way you turn is a beautiful mix of pastel colors buildings and those blue domes! It's worth it to allow for at least 15 minutes here to get all of the views and a photo or two of yourself!

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From here we continued down the main pedestrian path which gets very crowded - so plan to potentially take a detour if you are here during the summer. We picked up beers for the walk (perfectly acceptable here) and stopped in shops along the way. One place I knew I wanted to stop in was Atlantis books. I'm a big book fan and I had read that this was such a cool book store I knew I wanted to visit it. I spent awhile here looking at all the books and ended up finding a Greek mythology book to take home.


We were starting to get hungry from here and knew that we had a hike ahead of us down to Amoudi Bay so we decided to head down the 300 steps to sea level. If you aren't up for the trek down or up, you can hire a donkey for what I expect would be a fun experience. They looked a lot more sturdy than I was feeling. We had planned on lunch at the Amoudi Bay Tavern based on reviews we read before hand and would definitely recommend it. We shared a ceviche dish, seafood pasta and a bottle of rose and finally got some sun and no wind while we ate at the waterfront.

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After all we ate, I was actually looking forward to the hike up which was actually easier than down. Our next spot was to Oia Castle which is a must if you are visiting Santorini. The spot of the old Oia Castle has beautiful views of the town and it's known to be the best spot for sunsets. When we were there it was already so crowded though, and since we loved the view of the sunset from our hotel room we scratched our plan to stay in Oia and decided we would just grab a bottle of wine and do the sunset on our balcony. Standing at the Oia Castle balcony was one of my favorite views from Greece. Seeing the town and how it is built into the rocks with all of the beautifully colored buildings was incredible. 

We spent some more time walking around some off the beaten path streets in town before heading back to Imerovigli on our ATV and popping into all the shops along the way. There are so many things to see and do here; I can see how people spend days walking around.


Day 2

We couldn't go to Greece and not spend a day on a boat! We had read that sailing was a great way to see the island from the water and booked an afternoon tour with Sunset Oia. This was definitely one of the highlights from our trip and we really lucked out with weather. The days seemed to be getting progressively warmer even as we got further into October and we were loving it. The boat was beautiful and there were only about 12 of us on board. We had splurged for a bit more expensive package with a less crowded boat and for the minimal price differential this was worth it. The boat we chose was the Amorgos Lagoon 520. One of the highlights was the lunch cooked onboard which was one of our favorite meals of the entire trip. We stopped for a few different swim spots and spent time lounging on the deck. It was a perfect way to spend an afternoon. For dinner that night we stopped for take out souvlaki near our hotel at Let's Eat which was quick, cheap and tasty.

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Day 3

Our last full day in Santorini was spent doing one of our favorite things in the morning - wine tasting. What was almost as fun was surprisingly our afternoon activity hiking from our hotel in Imerovigli to Fira town. We hadn't seen this part of the island and didn't know how the hike would be but it was such a fun way to get from here to there and the walk was incredible. We left early in the morning for our tour with Santorini Wine Adventure Tours. Our guide was so knowledgeable and is actually oenology professor at a University in Athens during the school year and wine tour guide during the summer months. The Santorini style wines weren't my favorite but we ended up loving Vinsanto, a white sweet dessert wine.

A little foggy from our morning spent in wine tasting rooms, we forced ourselves right back out the door in the afternoon to make it to Fira. We had dinner reservations at night in Fira town at Argo so we planned to stay until then. From the moment we left the hotel the walk was so scenic I couldn't put my camera down. Planning this trip, I heard so little about the other towns in Santorini outside of Oia so it was a nice surprise to find that we liked Imerovigli, Firostefani and Fira just as much.

We loved every minute of our time spent in Santorini and while we definitely could have stayed for longer, three full days was a good amount of time to see the island and get a feel for all of the towns for the first time.

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