Santorini, Greece

After leaving Athens, we spent 4 days on the Greek Island of Santorini. Once we got to the island we didn’t have much of an agenda, which is one of my favorite way to travel. We had general ideas and of course restaurants tagged, but that was about it.

We decided pretty quickly that we wanted to stay in the town of Oia (pronounced E-ah), since it is the most well know village (and arguably most picturesque) on Santorini. Unfortunately, it was the end of peak season (late August) and options in our price range were a little sparse. Thankfully we found an awesome hotel about a 5 minute walk from the edge of the city proper. The front desk worker, Ana, was one of the most memorable people I’ve met while traveling. She was so accommodating, warm and enthusiastic about her home, which is a good way to describe almost every Greek we met.

We had 4 days on the island so below I’m going to hash out what we did, saw, and of course ate.

Day 1: OIA

I’ll say it once and I’ll say it again and again, my favorite thing to do in any new city is spend my first day wandering. And wander we did. If ever there was a city to explore side streets, staircases, and small alleys—it’s Oia. Between the iconic blue domes, quaint little churches, blooming Bougainvillea, and old windmills around every turn, it’s the perfect city to get lost in. We stopped in Atlantis Books so I could find Harry Potter in Greek, ate gelato at Lolita’s, and ate an early dinner on Melitini’s terrace. We then hurried to the other side of town to get a glimpse of Santorini’s famous sunset. It was the perfect casual day to start our adventures on Santorini.

Day 2: FIRA

Our second day on Santorini we decided to be ambitious and hike from Oia to Fira. The hike is 6.5 miles and has elevation gains in both directions. I would definitely suggest doing this hike either in the morning or later in the afternoon when the sun isn’t quite so severe. We got nice & sweaty trekking the cobblestones, dirt, and paved paths. It’s all worth it though, because along the way you will have amazing views of the Caldera, small churches, and the beautiful blue water below. It took us about 3.5 hours with plenty of photo stops. You will pass through towns along the way if you need to stop for food or water, but plan accordingly especially if you are hiking during the hotter summer months.

One of the highlights of the whole hike was stopping at the Profitis Ilias Church. We met a cute older man who’s family had looked over the church for generations. Despite the language barrier, you could tell he was so proud and excited to share his love of the church. Plus it was a welcome respite from the heat.

We continued on and finally arrived in Fira which is the capital of Santorini and the largest town on the island. We wandered a bit before finding a nice bench in the shade to people (and donkey) watch until it was time for dinner. Because of our unwavering dedication to finding good food and our lack of a reservation, we camped out 30 minutes before the restaurant, Salt & Pepper, opened to ensure we got a table. We were one of the few who were able to snag a table before they started to turn people away. Definitely worth it though, because the food was delicious and the owner was a character to say the least. We left the restaurant with our purses filled with candy (given to us by said owner) and caught the bus back to Oia.

Day 3: DAY OF LEISURE IN OIA

What’s a trip to a greek island without a day lounging around? We spent the morning unwinding by our hotel pool, doing tarot spreads, and making the most of our pool side balcony. After our relaxing morning and early afternoon we tackled our goal of the day—getting a good spot to watch the sunset.

Without a doubt, sunset viewing is the number one tourist attraction of the island. We grabbed an early dinner, filled a thermos with wine and headed over to the ruins of the Castle of Agios Nikolaos. The edge of the ruins looks over the white washed city, giving you a perfect backdrop for the sun to set over the ocean. We camped out and found a spot 2.5 hours before sunset and slowly watched as the castle platform and surrounding streets filled with people for the main attraction. Thankfully the people watching was aplenty and the view was stunning, so the time went by pretty quick. When the sun finally disappeared over the horizon the crowd applauded. My travel companion, Bre, said it best, ”I hope people always clap for beautiful things like the sun.”

Day 4: BLACK BEACH & PYRGOS

Our final day in Santorini we decided to venture to the other side of the island. We took a bus to Perissa, located on the southern east coast of Santorini. Perissa sits at the base of Mesa Vouno Mountain and is famous for its dramatic Black Beach. The entire beach is made up of small volcanic pebbles giving it it’s black color. If we had more days on Santorini, we definitely would have taken advantage of the many chaise loungers for rent on the beach, instead we opted to walk the beach, go into town for lunch and then head to our second city for the day - Pyrgos.

Pyrgos wasn’t originally on our radar, but last minute we decided to add this little town to our list (mainly due to it’s proximity to a winery!). We got there by bus and were easily able to walk around the whole town. We loved the small village and it’s laid back vibe. It was nice to explore the white washed town without all the tourist traffic of Oia or Fira. Between quiet streets, cute kittens and a donkey that really worked the camera for me, Pyrgos was a delightful venture.

A quick 10 minute walk from Pyrgos brings you to Santo Wines. The winery looks over the caldera and has a huge patio to sit and enjoy some wine. We did a wine tasting as we creeped on a wedding happening on the property and enjoyed our last Greece sunset (for now).

FOOD RECOMMENDATIONS ON SANTORINI:

Lolitas (Oia): I’m not exaggerating when I say we structured days around getting gelato at Lolitas. Seriously, it’s a MUST if you go to Oia. Our favorite was the plain vanilla (because we basic), but if you are adventurous the rosewater and pink pepper was also real good. Hands down some of the best gelato I’ve had.

Melitini (Oia): This was our first dinner in Santorini and it didn’t disappoint. Melitini serves Greek tapas. Our favorite was definitely the pita bread with a variety of hummus and dips. We also finished off our meal with some killer chocolate mousse. You’ll definitely need to make a reservation here, especially if you want to sit on the rooftop patio.

Salt & Peppa (Fira): Salt & Pepper specializes in home cooked traditional Greek food. We found out about this gem of a restaurant from a friend for both the food and atmosphere. The food was excellent (seafood pasta for the win!), and the owner kept us entertained the whole evening. They only have a few tables available that they don’t reserve every night, so if you don’t make a reservation, make sure you get there early!

Vanilia (Firostefani): We stumbled upon Vanilia while searching for restaurants around Fira that would be open late (yay for 2am flights). Located in Firostefani, they have a rooftop patio that overlooks the central square and caldera. This was the best Moussaka that we had in Greece. Eggplant, beef, and bechamel sauce baked to perfection! Paired with red wine, and a chocolate mousse for dessert, it was the perfect exclamation point on our trip to Santorini.

Have you ever been to Santorini? What were your favorite places? Let me know in the comments below!