It’s not my fault that the Sisterhood of the Traveling Pants books and movies resulted in a lifelong urge to travel to Santorini…
I mean I went with my boyfriend, but I was really looking for Kostos. Just kidding, Davide. Kind of.
Neither of us had ever traveled to Greece and we’ve been talking about going there for our first trip for years now, but we had no clue how to choose our dream destination. Did you know that Greece has over 6,000 islands? Only about 200 are inhabited, but that’s still a lot of options, man.
For a while, we just typed in different Greek islands, stared at the Google image results and stared at each other. Then we did some eliminating, stared at our hands, and finally admitted that we both had Santorini bookmarked in our brains. Santorini is to Greece what Coca-Cola is to soft drinks or Nike is to sportswear. Top of mind.
We found a direct flight from Milan to Santorini for a good rate, and settled on a cute and affordable hotel without many bells and whistles that was walking distance from the main drag of Fira. There was no caldera view, but to my surprise we had a sweet little terrace with a view of the ocean.
We were on the island for a full week so we decided to rent a motorcycle. This alone was pure entertainment for me. I giggle like a little kid when I get to ride on the back of a Vespa or motorcycle. For Europeans or American kids with Harley Davidson-loving dads, it’s no big deal. For me, it’s the Lizzie McGuire movie come true. Are you seeing a theme here? The media of my youth shaped me.
Santorini
- In a word: Dreamy
- Famous for: Whitewashed buildings with blue domes, cliffside cities, never-ending ocean views, donkey sightings, Lena & Kostos’ young adult love story
- What to Eat: Moussaka, Darma, Fava, Tomato fritters, Lamb, Greek salads, Tzatsiki sauce, Pita bread, Greek yogurt, Baklava, Fried feta
- What to buy: Artwork, jewelry, olive oil, volcanic-derived products
- Words to know: Kaliméra (good morning), Efcharistò (thank you), Yamas (cheers!)
Where To Stay In Santorini
We found a direct flight from Milan to Santorini for a good rate, and settled on a cute and affordable hotel without many bells and whistles that was walking distance from the main drag of Fira. There was no caldera view, but to my surprise we had a sweet little terrace with a view of the ocean.
The island is small, but it takes about 45 minutes to an hour to get from one end to the other by car, ATV, or scooter. You can also take the city bus to different areas, but you’ll be at the mercy of the bus stops and limited schedule. In any case, it helps to choose your accommodation in the area that peaks your interest most of all.
If you’re like us and are absolutely clueless about what area of the island to stay in, here’s a quick and dirty guide based on what I gathered from our week of zipping around Santorini.
There are plenty of other little cities and sections to check out, but these four hubs are great starting points for doing research. If you rent a vehicle of some sort, you can basically stay anywhere and make your “commutes” a scenic part of the adventure.
What To Do
Explore the Cliffside Towns of Fira & Oia
These two cities are the characteristic backdrops of Santorini. Brimming with cliffside infinity pools, vibrant flowers, and white buildings with the typical deep blue domes, you’ll find you want to stop to snap a photo every two minutes. Both Oia and Fira have lovely promenades where you can stroll along the avenue and admire the caldera view, pop into shops, and stop for a panoramic drink or meal in a cafe. You can also wander further down into the maze of vertical hotels or trek down a ramp on foot or via donkey.
Watch the Sunset in Oia
The sun rises in the east and sets in the West and the lovely town of Oia is perched neatly on the North East corner of the city. This makes it the perfect backdrop for watching the evening sun dissolve behind the dark blue blanket of the ocean. There’s a popular vantage point in the tip top corner of Oia with a little terrace where people sit on the wall, drink a beer on occasion, and watch the sun go down. If you want to get a seat with a view, you’ll have to get there extremely early. We tried going an hour before sunset and couldn’t see worth a damn so we went back (snacks and drinks in hand) three hours early one night to stake out the perfect view.
Take a Catamaran Cruise
This is a must do. If you can allow for it, splurge on a Catamaran cruise so that you can experience Santorini and its pristine waters from the ocean. We took a five-hour sunset cruise that stopped at Red Beach, the volcanic hot springs, and a few other spots where we got to dive off the boat and swim around. They served us dinner with unlimited wine (post-swim, thank goodness) and we watched the sun sink down behind the horizon before heading home. There are different packages you can buy starting at around $75 per person so it costs a bit, but it’s worth it. We were on a more modest cruise, but we still had a blast and made friends with some cool international folk. The more you spend, typically the bigger the boat and bigger the party vibes.
Check Out the Red Beach
On our first day, we zipped down the coastline to the south of the island to explore beaches and figure out what areas we liked best. Red Beach was our first stop, and although we didn’t end up going back on our own, it’s definitely a spot worth seeing. You have to do some minor rock scaling (maybe three actual minutes of watching where you step) to arrive at the red sand beach set against a backdrop of jagged, siena-coloured cliffs. This is a great spot for snorkelers and there’s a little beach bar as well.
Spend A Day Lounging in Perissa
The area surround Perissa was by far my favorite stretch of beaches and the most beautiful spot for sunbathing and swimming in my opinion. There are abundant beach bars offering free sunbeds and umbrellas as long as you plan to eat or drink there, which I think is genius. People gotta eat, right? The sand is black in this area – a relic of the volcanic explosion from three thousand years ago – and the water is crisp, clean, and clear. A lot of the beaches on Santorini are more rugged, but this stretch is comfortable for all day sun & surf.
Hike From Fira to Oia (or vice versa)
We didn’t end up doing this since we spent most of our time zipping from here to there on the scooter, but there is a scenic hike you can take from Fira to Oia that snakes along the cliffs with the ocean below. If you want to really relish in the landscape of the island, this is a great option. The hike takes about three hours one way.
Explore the towns of Pyrgos or Megalochori
The two little towns of Pyrgos and Megalochori are traditional villages with charming little streets and a taste of real life. They’re still tourist destinations but aren’t as heavily frequented as Fira and Oia. We spent a morning wandering through the enchanting town of Pyrgos, stopping for breakfast, photos, and moments to coo over the magical scenery.
Check Out A Winery
Our hotel “concierge” or rather, the man who sat in a plastic chair in the hotel courtyard and chatted with us every morning, suggested we visit Santos Winery. It’s a bit outside the center of Fira, perched high on a hill, and he said they had fair prices, good wine, and great views. There were also several other wineries peppered around the island and grape vines that makeup the landscape attest to how much wine is a part of the Santorini culture. We didn’t get a chance to do this, but I would definitely pencil it in (and call a donkey to take me home) the next time.
If you’re more of a beer lover, Santorini produces local, craft beers called Yellow Donkey, Red Donkey, Black Donkey, Crazy Donkey…you get the gist. Adjective Donkey. There’s a little brewery 10 minutes south of Fira on the way to Kamari where you can try them out or you can find them in most of the restaurants and cafes.
Rent Something and Cruise Around
I would highly suggest renting a motorcycle or ATV for at least a day or two during your trip. Not only is it the perfect way to cruise around Santorini independently, it’s also the perfect way to feel like a movie star. I’m talking salty air, sea breeze in your hair, donkeys glaring out at you from rugged vineyards, picturesque white and blue structures springing up in tumbling waves, a volcanic island making cameos in your rearview and the expanse of the ocean circling your route. Sounds pretty dreamy right? It is.
We were on the island for a full week so we decided to rent a motorcycle. This alone was pure entertainment for me. I giggle like a little kid when I get to ride on the back of a Vespa or motorcycle. For Europeans or American kids with Harley Davidson-loving dads, it’s no big deal. For me, it’s the Lizzie McGuire movie come true. Are you seeing a theme here? The media of my youth shaped me.
Try Some Water Sports
There are plenty of aquatic entertainment options, especially around the Perissa and Kamari beaches. Davide and I rented a jet ski and I laughed like a hyena as we zoomed across the water and did sea donuts without restraint. So. Much. Fun. You can also go tubing, do the hoverboard thing, go wind surfing, or even take a horseback ride along the rocky coast.
Eat, Drink and Eat Some More
Try all of the local delights that Greece has to offer! Greek salads, moussaka, tomato fritters, Darma grape leaves wrapped around rice, tzatziki sauce, pita bread, and seafood, are all specialties of the island. Splurge on at least one hearty dinner, preferable somewhere with a view, and some wine during your trip. Greek food is so rich and culturally unique so be adventurous when ordering.
Fun Facts About Santorini
- The official name of Santorini is actually Thira. For a while, the island was also called Kalliste, which poetically translates to “the most beautiful one.”
- The island – which has somewhat of a crescent shape with an extra tail – used to be round until the volcano erupted in 1500 BC, causing chunks of land to sink down into the sea and separating it into smaller islands.
- Some sustain that the sunken part of Santorini that imploded into the sea when the volcano erupted is rumoured to be the lost city of Atlantis.
- About 15,500 people actually reside on the island while typically 2 million people visit annually.
- Caldera is the name for a volcanic crater. “Caldera views” indicate those which face the volcano.
If you head to Santorini, let me know what your favorite activity or moment from your trip ends up being in the comments. Yamas!
