Our most recent European family vacation ended in Santorini and everyone agreed that it’s definitely worth the hype. We’ve all seen the pictures online of Santorini sunsets and the famous blue dome church, but the real-life views exceeded all expectations. Four days felt like the perfect amount of time to get some exploring in, but also some relaxation which was much needed after traveling around Europe for the last nine days. The first half day is spent traveling and there is a fifth day is built in for traveling back home, so technically you will only have 3 full days. Feel free to add on extra nights if you need some additional R&R.
Be sure to make dinner reservations at least a few months in advance, especially if you are going during their busy season. If you are wanting to eat at Pelekanos, which was very highly recommended for a sunset dinner, make those reservations at least 6 months in advance. We missed out on eating here because they were already booked 4 months out for sunset times. Important to note that 1) this itinerary is assuming you are staying in Oia and don’t need to travel to get there every day and 2) you have booked an accomodation with a pool. Both are highly recommended to get the most out of your stay.
Day 1
Arrive in Santorini this afternoon. We were traveling from Florence so we arrived by plane after a short layover in Athens.
Arrange for a private transfer from the airport to your accommodation. This was similar pricing to getting a taxi and much less stressful. We paid 55 euros total for a large passenger van for 6 of us. Transportation was arranged by our Airbnb.
Check out our Airbnb here: https://abnb.me/odIsKt5qxqb
Spend the next few hours unpacking and relaxing at the pool.
If you want to get a good spot for sunset, head over to “sunset boulevard” about 1.5-2 hours before the sun is supposed to set. Since sunset boulevard isn’t an actual street name, type in “Vitrin” to your maps app and head that way, you can’t miss all of the people lining up. The most popular viewing spot is the Castle of Oia, but you need to get there at least 2 hours before the sun sets to get a good spot. If you don’t care about getting the best seat in the house, walk over around 30-45 minutes early and find a good view, this is the option we chose most nights.
Make dinner reservations at Sphinx about 45-60 minutes after the sun sets. Make sure you book rooftop terrace seating.
If you’re in the mood for dessert, stop at Melenio. They have a restaurant up the stairs, but if you go down the stairs there’s a pastry counter for takeaway.
Day 2
Breakfast at Melenio Café. You can sit on their patio which has views of the caldera, or you can order takeaway for half price.
Spend the morning exploring Oia and checking out the shops. There is one main road through the city and there are no cars.
After you’re done shopping, spend the rest of the morning at the pool until it’s time to head to lunch.
Walk over to PitoGyros for lunch. If you want to eat at the restaurant, I recommend getting there right when they open at 11 AM. We ate here multiple times and every time we ordered at the counter and did take away and brought it back to our Airbnb to eat with a view.
After lunch, walk to the Oia Bus Terminal and get on the bus to Thira (also spelled “Fira”). You will need to pay cash but there is an ATM near the bus stop, as well as a bathroom. Pricing when we went in May 2022 was 1.60 euros one way. Time tables are available online (we used santorinisecrets.com), however, they were not always accurate so get there about 30 minutes before the bus is scheduled to leave. The line usually starts in front of Piatsa Slouvlaki Grill House (not in front of the electronic timetable or bus stop sign across the street). Sometimes the line can get long and you’ll have to wait for the next bus which could be 30-60 minutes. If you get there early enough during the busy hours they will start selling pieces of paper they use as tickets and you will be guaranteed a spot on the bus (this is not a scam). The bus is a large coach bus, not your typical public transportation bus.
Take the bus into Thira for a wine tasting. We walked to Avantis (now Anhydrous) and did the “Anhydrous Experience” tasting which came with tasting 4 wines and a generous-sized snack platter for 15 euros. We were able to walk in but they did recommend reservations during their busier times. Another winery that was highly recommended was Santo Wines due to the views. Avantis didn’t have any views but the wines were great and it was reasonably priced.
Head back to the Thira bus station and hop back on the bus to Oia. Spend the rest of the day relaxing at the pool and enjoying the views.
Make dinner reservations at Pelekanos for sunset. If you weren’t able to get into Pelekanos, Roka is another great option.
Day 3
Two options for this day depending on how you are feeling: hike or pool. Joseph and I chose to do the hike from Thira to Oia which we highly recommend! There were a few steep sections but the majority of it is very well paved and you get amazing views the entire way. The rest of the family chose to shop around Oia some more and hang out at the pool.
We went to lunch at Niko’s place this day to try another gyro place, again we got takeaway and ate at the Airbnb. However, we decided Pitogyros was better so if you don’t mind eating at the same place for lunch every day, I would go back there.
After the hike, put on your swimsuit and spend the afternoon at the pool. If you get hungry for an afternoon snack after your morning of hiking, check out Vitrin. They have great crepes and even better views. Since this is near the Castle of Oia, you could head straight there from Vitrin and camp out for sunset. Get a bottle of wine to sip on while you take in the views.
Make dinner reservations at Skala about 45-60 minutes after the sun sets.
Day 4
We went during the time of covid testing requirements, if that is still the case then go ahead and get tested this morning for your flight tomorrow. There is a pharmacy in Oia that does rapid testing for 15 euros, we were in and out in under 10 minutes.
We booked an all-day private catamaran tour this day. For 6 people, it wasn’t too much more to do a private tour than it would have been to pay for all of us to be on a boat of 30 people. We used GetYourGuide to book and we booked with Sail Away – Santorini Catamaran Sailing. The lunch that was provided was incredible and it included unlimited beer and wine. We were able to stop near the volcanic hot springs and jump in for a swim. They don’t take you into the hot springs because of how crowded it gets with all of the large boat tours, which we appreciated. We also stopped by the white and red beaches to view from afar.
The water was a little choppy on the way back so be prepared if you tend to get seasick like a few people in our group. If you don’t book with Sail Away, I highly recommend booking with a company that will arrange to pick you up from your hotel/Airbnb or at least at a nearby pickup spot if you are staying in Oia where no cars are allowed in the city center. If they offer it at an additional cost, keep in mind that additional cost likely won’t be too much more than getting a taxi there and back, and a lot less of a headache.
We were dropped back off in Oia around 4:30 PM. After we showered and changed we were in the mood for an easy dinner, of course at Pitogyros.
Choose your sunset adventure and leave at the appropriate time. On your way back to your room, go ahead and get dessert at Melenio café one last time.
Day 5
Travel day. Make sure you arrange for a transfer to take you from your accommodation to the airport so you don’t need to stress about getting a taxi or getting on the bus. Get to the airport and head home or to your next adventure.
I hope you enjoyed this 4-day Santorini itinerary! Let me know what itinerary you would like to see next.
