Santorini is THE picturesque destination we think of when we think of Greece. The classic dome white buildings with blue rooftops, pink Bouganvillea flowers draping along the walls, and the clamoring blue sea in the close distance.
It was everything I imagined, but 10x more magical in person. Santorini definitely made the list of the most romantic places in the world.
The island itself is located on the south side of the Aegean sea and is part of a collective of islands called the Cyclades.
It’s extremely busy with tourists all year round, even during COVID-19, which is why I recommend going at the end of September (where clubs and beach clubs are just about to shut down but not quite). Late September, it’s still swelteringly hot, but not nearly as unbearable.
There are some unbeatable experiences you can’t miss out here in Santorini. Follow along for a three-day full itinerary for what to do in Santorini.
Day 1
Check into a Villa
Santorini is divided into several different ‘villages. Obviously, the main villages (think downtown) like Thira and Oia have all the nice restaurants, clubs, and shops, as well as the most luxurious hotels cascading over the ocean. Of course, you can definitely score one of those hotels with infinity pools and views of the ocean at your doorstep, but it’s going to cost you quite the fortune.
I’ve compared below the average price of the top 5 rated hotels in Santorini during peak season per night (keep in mind prices are almost halved during shoulder season ie. March).
Hotels from (left to right): Santa Marie Oia Luxury Suites & Spa, Santorini Princess Spa Hotel, Cavo Tagoo Santorini, Canaves Oia Suites, Volcano View Hotel Santorini.
If you’re looking for something more on the affordable end, I would recommend getting a hotel in another village. I stayed in Karterados and by car, it takes 5 minutes to get downtown. It didn’t cost me more than $100 CAD a night, for a private room with 3 twin beds, a dresser, and a pool right outside my doorstep.
If you have a group of people, I would recommend getting a spacious Airbnb. The amazing group of women I met on a trip rented out the most insane villa I’ve ever seen. Private beach, private pool, cave bathrooms, and a huge outdoor area complete with dining table, sofas, lounge seats. This was around a 15-minute drive to downtown, Thira.
I link this Airbnb here.
Lunchtime in Thira
After you settled in, it’s time for lunch!
I chose a restaurant that was decently priced and had a direct view of the ocean. You’ll feel like you’re having a luxurious experience without breaking the bank. You can find many souvenirs, clothing shops, and restaurants in Thira and Oia.
Food in Santorini consists of fresh, Mediterranean cuisine. Think of dips— hummus, tzatziki, eggplant spread with pita. Fresh seafood— octopus, calamari, fish, and grilled meats, salads, and pilafs. Of course, don’t forget the greek wine.
Afternoon Wine Tour
On that topic, the one thing I didn’t have time to do was a wine tour. Greece is well known for its locally produced wines. You can easily find half-day wine experiences online through GetYourGuide, Viator, and Airbnb. Engage in a half-day group tour and taste a variety of local wines. It can also be a fun way to make new friends with other travelers. There are even ones that end in Oia to catch the sunset.
The sunset in Santorini is something that you simply cannot miss. Most people, including my native Greek friend, recommend the absolute best place to see it is from Oia.
Barbeque at Home
Because eating out in Santorini can get quite expensive, another option is to buy local produce and meats, pick up a couple of bottles of wine and have your own barbeque at home. Many of these villas come with the equipment. If you have company, this can be a gorgeous way to end off a long day of exploring. You can also take a dip in the pool before or after, or during (no one’s judging here!).
Day 2
Thira to Oia Hike
Hopefully, you had a good night of rest in your new stay. I recommend waking up early and embarking on the hike from Thira to Oia.
Disclaimer: this has ought to be one of the most gorgeous hikes I’ve ever done in my entire life, and I come from British Columbia (we’re famous for our backyard of mountains and nature).
This hike officially starts at the Atlantis Hotel in Fira and will span across parts of downtown Thira, through the corridors with views of the ocean at every angle, and also parts where’s it’s more dirt road.
Early in the morning, there are not many people so you might find yourself alone in this tranquil hike. I got so lost in the sheer beauty of Santorini.
You’ll also come to a part of the hike where there’s a big cliff, which I was scared to climb all the way. If you get tired, you can stop at the mom n’ pop fruit stands for a refreshment or rent a donkey that will take you directly to Oia (for 20 euros).
Finally, enjoy a well-deserved lunch in Oia at a restaurant with a view of the ocean. Past noon, Oia will be bustling with tourists. It can get quite hot if you’re there mid-summer-early fall, so I recommend heading back to your hotel for a mid-day dip before continuing your evening plans.
For dinner, I would recommend doing something a little more interesting. Ever watched “Mama Mia!”? It’s a classic American movie about a jovial Greek family, and they play it at the open-air cinema at the restaurant Volkan on the Rocks in the evening. You can have a great dining experience while watching the movie from the projector.
Nightclubs in Thira
You have to try the night scene in Santorini! Even during the slow season, the club is bustling especially after 12 am. I loved the open concept of the club we went to called Koo Club.
There were two floors and VIP lounges all in the open. We definitely kept the champagne flowing that night, and although I can’t quite say I remember much (or have any pictures I can show on here), everyone there definitely seemed like they were having a blast.
Day 3
After a wild night out, it’s time to relax! And this time it doesn’t require you to move at all. My new friends came and picked me up in a party bus, and then took us to the port to start our catamaran cruise. This boat was quite spacious, so plenty of deck space for those Instagram photos.
This tour was all day long, meaning we got to explore different swimming spots and do the famous volcanic swim. The captain also provides a full spread of barbeque, dips, and pita for our apres-swim meal. I would definitely recommend getting this experience. It’s not every day you get to sail across the Aegean sea.
Of course, the ride ended off with watching the sun literally set over the ocean. It was mesmerizing, glorious sight.
Conclusion
That concludes my full, but still relaxing itinerary for Santorini. Santorini is definitely a timeless vacation destination, and one of those places you’ll always have fond memories of.
Let the ocean, beautiful jarring landscape, and warm people take you away. It’s one of those feelings that’s just hard to describe in words, but you just have to experience it in person.
Secret Prose 
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