Exploring Santorini for 3 Days


It’s the middle of the day when my phone lights up with a text from a friend stating, “Flights to Santorini are on sale!” Pictures of the white architecture all along the calderas, against the blue waters instantly filled my head. I knew I would visit Santorini one day, but expected to fly into Athens and then go from there. I never even thought of the possibility of flying directly into Santorini due to the typical high costs, especially during the summer. So, within a few hours, I locked down a date (4th of July weekend of 2019) and convinced my sister, best friend, and my best friend’s husband to join me. The flights cost around $600 roundtrip from DC to Santorini and then I applied to the American Airlines credit card at that time, which deducted $200 from my fare.

Our trip was going to be quick because I already had other trips planned for the year and couldn’t use up too much PTO, but we’d still get 3 full days in the magical Santorini. I absolutely loved this place with all my heart. The beauty was just breathtaking where I could never get tired of it. Initially, I was worried because I hadn’t plan that many activities, but quickly discovered that simply walking around town and taking in the views was enough for me. I definitely advise visitors to do the same!

That being said, here are some details from our trip that are absolutely musts.

Stay in a Villa with a View

The extra money spent on accommodation with a private pool, balcony, or simply views of the Mediterranean Sea is well worth it. I believe it’d be hard to find a place WITHOUT stunning views, but definitely get one where you’ll wake up each money and still be in awe.

We stayed at Lilium Villas in Fira for our three night stay. I cannot recommend this place enough! The staff were all so friendly, breakfast included, free shuttle into the town of Fira, walking distance from Santo Winery, and of course the beautiful views. The rooms itself was pretty standard and plain, but each room has a large balcony. My best friend booked a room with a private hot tub, so my sister and I hung out there as well.

Upon checkout they even gave us a book to take home with us. When the staff realized that my sister and I didn’t live together, they gave us another so we both would have one! And then they proceeded to tell us that we could hang out by the pool all day until we had to head to the airport. By then we were all too tired to go back into town, so that was exactly what we wanted to hear.

Drink Wine at Santo Wines Winery

This beautiful, large winery is where you need to go to catch the sunset at least once during a stay in Santorini. Seating is plentiful here, but I would still recommend making a reservation. I reserved a table for 4 at a time where we would be able to enjoy the daylight and the sunset. Yes, that means we spent plenty of time at Santo Wines Winery. Since I selected to reserve a table on the first row where food must also be purchased, we scored the best seat in the house. We basically had a whole section to ourselves and the waiter positioned our table perfectly so that we would not be disturbed by others trying to get photos of the sunset.

We ordered two tastings, dinner, and bottles of our favorite selections. Our waiter was so knowledgeable and helpful when describing the wines we were trying, which made it an even greater experience. The wines were great even the whites, which I always lean more towards reds. There’s a store near the entrance where you can purchase bottles of varying sizes along with other souvenirs.

Have a Photoshoot Around Town

Everyone knows that Santorini is the perfect place for photo opportunities. There are so many spots that are way too gorgeous that you need to whip out a camera. Whether you snap photos of just the landscape, hire a photographer, or have your sister take your pictures (my option), taking photos is a must. I know some travelers like to emphasize living in the moment and not behind a camera lens, but just ignore that for this trip. Strike a pose and capture those beautiful moments.

Have Lunch and Watch the Sunset on a Boat

The water surrounding the island is way too perfect for visitors not to go out to sea. We booked our boat ride with Santorini Sailing for about $120 per person. This included roundtrip transportation to the port from our hotel, lunch, beer, wine, and a half day boat ride. The ride to and from the port is not for the faint of heart, so just a warning.  Lunch was surprisingly very tasty! They prepared Greek bbq on the boat as we looked upon the Oia calderas. They stopped plenty of times for guests to take a dip in the sea and then we watched the sun go down before sailing back.

Sit in a Restaurant Overlooking the Calderas

This one is hard not to do because almost every cafe and restaurant has great views. So, just make sure to snag a table along the side and relax while appreciating the beauty of Santorini. For this trip, I didn’t make any reservations to restaurants aside from Santo. Instead we simply stumbled along the walkways and stopped in any one we were drawn to.

Spot the Blue Top Churches in Oia

We caught an easy and cheap bus ride from Fira to Oia. Simply walk to the bus station in the town of Fira, hop on the bus heading to Oia, and pay for the fare on the bus. It’s a nice, clean bus and about a 30 minute ride. Usually the pictures you’ll see of Santorini is of Oia with the infamous blue tops, which signifies a church. Definitely make your way out to this town if you’re not already staying there. There are tons of shops, cafes, and restaurants to explore.

Eat a Gyro at Pito Gyros

Pronounced YEE-roh. I cannot emphasize this enough – it is my pet peeve when people pronounce it with a J. I’m craving one now as I’m writing this. You can find gyros all over, but Pito Gyros has raving reviews and recommendations. It’s cheap, filing, and so good. Pair it with a beer and you’re all set.

Walk, Walk, and Walk Some More

As I mentioned earlier, get your steps in! This island is best to explore by foot in each town (or ATV if going a far distance). Walking gives you the opportunity to stop into any place you find interesting and just allows to explore every inch of the area. Granted, it may take you even longer to get to a destination because you’ll want to stop so much to take pictures and gaze at the calderas…but it’s 100% worth it.

Eat Greek Cuisine

This is of course a given when visiting any country. You NEED to indulge in the local cuisine. However, sometimes when I visit certain places I find myself craving my go to – Asian cuisine. That was not the case here at all. I could not get enough of Greek food. Everything from salads to bread to chicken souvlaki tasted incredible. Below you’ll see two large plates of tzatziki, which normally I’d think wow that’s way too much to eat. Nope. Not the case at all. It was so fresh and light that we needed more pita to wipe the plates clean. Trust me, your stomach will be very happy during a visit to Santorini.


Santorini is more beautiful than you could even imagine. Pictures are gorgeous, yet they really don’t do it justice. You really need to go see for yourself!


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