Santorini Beyond Oia: A Roadtrip Exploring The Island

Located in the Cyclades, a group of about 220 islands southeast of mainland Greece, Santorini is the most-visited island in Greece, and certainly lives up to the visions of white-washed houses, blue domes, and bright pink flowers.  But many people come and only spend time in the famous, expensive, crowded towns of Oia and Fira—which is such a miss.

But what you’ll find if you venture outside of Oia and Fira is that it’s an island filled with unique landscapes, culture, medieval history, family-run wineries, and a much chiller vibe.  A Santorini roadtrip is the perfect way to explore the entirety of this famous island, and I’m going to share all the places you need to go!

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What to wear on your Santorini roadtrip

From a clothing standpoint, you want something breathable and loose.  If you’ll be going inside churches, you’ll need to be able to cover your shoulders and that your knees aren’t showing.  For me, I’m a dress girl so went that route.

This sundress from Amazon was super comfy (and covered my shoulders and knees).  I paired it with these cute and comfy white Olukai sneakers.  I knew white would be a little ballsy in certain spots (like the Black Beach and Red Beach), so I brought along my all-time favorite walking sandals to slip on when needed.

For my day of wineries, I wore my go-to travel pants from Athleta (their Brooklyn Ankle Pant).  They’re lightweight and breathable, dry very quickly, and are stretchy so can do active things while still looking super cute.  I paired it with a thin breathable top from Loft, and my cuter Aerosoles (like this or this) since I wouldn’t be hiking.

I brought along my trusty cross-body purse and plenty of sunscreen (here are my favorites).   It is HOT in Santorini (even in mid-September it was boiling hot) and almost never shaded, so a hat would be a good idea as well.  And obviously if you plan to spend time at the beach, a swimsuit and towel are important.

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How to get around Santorini

You can see the general shape of the island of Santorini in this photo (well, the northern half)…the island is basically a backward “C” facing a larger island (Thirassia) and some smaller islands across the caldera (the crater formed by a volcanic eruption, which in this case is filled with the Aegean Sea).

On the northern point (right side of this photo) are the towns of Oia, Imerovigli, and Fira, where most tourists stay.  In this post, we’re visiting spots in the middle and south parts of the island.  It’s not that it’s a huge island (most places are 20-25 km from Oia), but you have to go the long way around to get back to Oia so the time adds up.

Many travelers will rent an ATV, car, or motorbike for their stay or just for the day, to get around.  This is easy to do and gives you a lot of flexibility in your itinerary.  There’s also the public bus that goes from Fira to just about anywhere on the island for 2 euros.

I ended up booking a private driver to take me around, just to avoid the hassle of renting, driving, parking, and then returning a car.  I used Santo Luxury Tours, owned by Nikos Drossos.  He tailored a full day Santorini roadtrip (and my half-day of wineries) based on my desires, and we were able to make changes on the fly as well.  I highly recommend him!

Where to stay in Santorini:  I spent one night at Aspaki Exclusive Hotel, and two nights at Charisma Suites.  Both were awesome, but I HIGHLY recommend Charisma!

You can see a couple pics of my Charisma room at the end of this post (my deep-dive review here), but it is in the perfect location, service & rooms were amazing, & it was easy to get to taxis too.  And here is my deep-dive review of Aspaki, which was also great and has blue dome views.

Other Greek adventures to help you plan your trip!

Sampling The Delights Of Santorini’s Wineries

Santorini At Sunrise: Solo Hiking From Imerovigli To Oia

Where To Stay In Santorini: Oia’s Gorgeous Charisma Suites

Review: A Splurge Stay At Art Maisons Aspaki Santorini (Oia)

Where To Stay In Naxos, Greece: The Best Beach & Mountain Hotels

Review: Staying At The Unique ELaiolithos In Naxos

Exploring Rina Cave On The Perfect Naxos Boat Trip

How To Spend A Day Or Two In Naxos Town

Views For Days: Why You Have To Visit Rotonda Restaurant in Naxos

An Accidental, Awesome Discovery of Agios Mamas In Naxos, Greece

What to include on your Santorini roadtrip away from Oia

There are soooo many things you could include on a Santorini roadtrip, and I did manage to cover a lot.  Below I’ll take you through all the places Nikos took me, from amazing viewpoints like Three Bells and Akrotiri Lighthouse, to traditional villages, to volcanic beaches, and much more.

Below I share everything in the order we went.  You can do this all in one day like we did, or just venture out to a couple places each day, and spend time by your hotel pool as well.

One thing to note is that I am NOT including wineries in this post, though they’re a common inclusion on a Santorini roadtrip—and I definitely recommend them!  I have a separate full post on visiting wineries in Santorini that you should definitely check out.

Before we dive in, I’ll mention a few places in Santorini that I didn’t get to:

• I wanted to go to Vlychada Beach with its cool cliff rock formations, but didn’t have time
• I did skip the Akrotiri ruins, often compared to Pompeii and considered one of the must-see things in Santoirini.
• I missed the traditional village of Megalochori (I was bummed about this, though visited two others)
• I didn’t spend any time in the beach towns of Kamari, Perissa, etc., though drove through
• From a restaurant standpoint, Metaxi Mas came highly recommended (reservations recommended)

Okay, let’s get started, shall we??

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Three Bells of Fira:  Prophet Elias Church & A View

Not to be confused with the famous Prophet Elias Monastery (which we’ll get to in a sec), tiny Profit Ilias Church (or Prophet Elias) is more commonly known for the Three Bells of Fira, one of the most iconic photo spots in Santorini.

The famous photos are not actually of that church, but a different one that overlooks the caldera.  You’ll often see this view in publicity images of Santorini.

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If you’re facing the Three Bells then Profit Ilias Church is at your back.  The church itself is small but cool looking.  It’s often closed, but the outside photographs nicely.  Though let’s be honest, we’re really here for that view.

However, Profit Ilias Church is absolutely STUNNING at sunrise.  I hiked the Imerovigli to Oia portion of the famous Fira to Oia hike, which this church sits along.  I was able to get here just as the sun was coming over the horizon, and it made for a pretty great photo subject.

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Profitis Ilias Monastery

When people say they’re visiting Prophet Elias, this is what they usually mean (not the church above, which is usually known as the Three Bells).  Built on the highest point of the island, the monastery of Profitis Ilias sits at the highest point of the island—about 1,800 feet above sea level. 

The monastery dates to the early 1700s—one of the oldest on the island—and is a great example of Cycladic architecture.  A few monks still live here and do the winemaking and other industries (olive oil, honey, etc.), so you can’t go into the monastery itself.

You *can* visit the chapel, however, which has Byzantine religious icons and colorful frescos.

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And even if the religious and historical side of Profitis Ilias Monastery isn’t as interesting to you, the views from the monastery’s courtyard are worth a visit.

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Traditional village of Pyrgos

Surrounded by vineyards and perched on the slopes of Mount Profitis Ilias, the medieval village of Pyrgos is a bit of a hidden gem in Santorini.  It certainly gets visitors, but is overshadowed by the famous Oia and Fira, and also a bit (in my opinion) by Megalochori village.

The beginnings of Pyrgos can be traced to the 13th century when the Venetians controlled the island, and it rose in prominence over time.  While it started off as a small town with a monastery, a large fortress was added in 1580 to be a strategic defense point, and many historians believe it was once Santorini’s capital (before it moved to Fira).

Nikos dropped me off at the base of the main town and I began climbing up on foot.  The steps wind their way around and up  the hill, giving myriad options of narrow streets and charming little shops and local restaurants.

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Let’s take a moment to appreciate the kitties of Pyrgos… 🙂

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I kept climbing toward to the town’s pinnacle, alternating between beautiful whitewashed houses and bright flowers, and glimpses of sweeping views toward the ocean.

This man was playing beautiful traditional music as people walked through the tunnel, and it added such a cool ambiance.

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Pyrgos is Santorini’s highest village (sitting in the shadow of Profitis Ilias Monastery), so it offers up some amazing views.  You can walk up to its peak and explore the ruins of the Venetian-style Kastelli (castle), enjoying 360-degree views across the island.

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After all that climbing in the heat, I definitely wanted a cold beverage and a bit of shade, so stopped in at Franco’s Cafe.  It’s one of a couple bars that sit at the top of Pyrgos, and I enjoyed a freddo espresso and a bit of quiet with my Kindle while soaking in the amazing views.

In fact, Pyrgos can be a great place to come for beautiful Santorini sunsets without the crowds, and with some great traditional Greek restaurants (I hear Penelope’s is good).  I’d recommend a sunset at Franco’s if you’re able to make it happen!

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Pyrgos has around forty churches scattered around the village, of slightly different styles.  It’s a great place to learn about the island’s traditional way of life, including visiting the Santorini of the Past Museum.

If you’re looking for a great spot to base yourself in Santorini that’s away from the crowds, Pyrgos would be a solid option…it’s big enough to have plenty of housing choices, and has great views and really good restaurants.

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The beach towns & south part of the island

From Pyrgos we headed to the south and drove along the coast through beach towns (with a quick stop for a coffee).  The south part of the island is very quiet compared to the insanity of Oia and Fira.

We also drove through Emporio and Megalochori but didn’t stop right then, because we had a destination in mind.  On a side note, Niko did mention that Fratzesco’s Fish Tavern in Perissa is one of the best fish restaurants in Santorini.

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Black Sand Beach

Because Santorini is an extinct volcano, it has some interesting geological sights…the black sand beaches are one of them.  It’s not just one beach, but actually a long one between Perissa and Perivolos, and then another at Kamari—all in the south of the island.

The juxtaposition of black volcanic sand and crystal-clear blue water is a big draw.  However, I should note again that Santorini is not the best traditional beach destination, and the black sand beaches especially are not the most comfy…the underwater panorama is rocky and can be dangerous for small children.

Personally I didn’t find the black sand beach terribly interesting (I thought the one in Maui along the Road to Hana was much more dramatic).  If I had to pick, I’d definitely go Red Beach over Black Beach.

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Traditional village of Emporio

Having already visited Pyrgos, I had trouble choosing between Megalochori and Emporio for my other traditional village in Santorini (I didn’t have time for all three).  Nikos suggested the latter as it’s where he’s from.

Emporio village is situated at the foot of Mount Profitis Elias, and is the largest village in Santorini.  Though there are signs of earlier settlement, historians think the castle town sprung up in the 14th century.  Note, it can be transliterated Emporio, Emborio (how it’s pronounced), Emborios, or even Nimborios.

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Like the other traditional villages, Emporio has plenty of the stereotypical whitewashed buildings, blue details, and brightly-colored flowers that you can discover along its tangle of narrow streets and alleyways.

It’s one of the best-preserved and most unique medieval castle towns in existence.  The castle and town walls were built to protect the town from pirate raids, which were common.

It also has some of the most interesting architectural designs (particularly churches) you can find in Santorini.  The first church below is Church of Our Lady Messani (or Church of Old Panaghia), the second is Palea Panagia in the Kasteli (castle), and I’m not sure what the third is.

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Snack stop!!

You all KNOW I love me some pastries, so Nikos made a quick stop at Grigori’s Bakery on our way to the Red Beach.  It was huge and had an overwhelming array of choices, from breads to sweet buns to cakes to baklava.

I decided to try out three different kinds of sweets…a chocolate baklava, a grape phyllo pastry, and a mastiha-flavored phyllo pastry.

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Red Beach

The same volcanic eruptions that gave us the Black Beach led to the formation of this vivid beach, which is very popular with tourists.  year.  The dark red and black pebbles and mostly-reddish-brown sand—framed on one side by deep reddish-brown cliffs and on the other by sparkling blue water—is quite an arresting combination.  

Also known as Kokkini Beach, the Red Beach is also on the south part of the island, very close to the ruins of Akrotiri.  It has a large parking lot (that’s often quite full), or you could visit by a catamaran tour instead.  I’m not certain what this little church complex is, but thought it was quite striking against the dark red cliffs.

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Once there, there is a small footpath that will lead you on a 7-minute walk to the beach.  The Red Beach is what they call “semi-organized”, which means it has a few umbrellas and sunbeds for rent, but does not have a beach bar.

So you should make sure to bring any necessary sun equipment, plenty of water and sunscreen (here are my fave sunscreens for travel), or buy whatever you need from the two shops right before the parking lot.

One thing to note…Red Beach is technically classified as “unsafe”, though this doesn’t deter tourists.  Landslides are common in this area and it seems like people are injured semi-frequently, so you need to be very aware of your surroundings and know that you undertake this at your own risk.

The beach’s sand is a natural color, formed from the black and red pulverized volcanic rock coming from the Santorini caldera and the bright red cliffs behind it.  Its underwater rock formations and interesting marine life make the beach ideal for snorkelers.

I just came briefly to take some photos, and moved on.  As you can see, some people plop themselves down for the day to soak up the sun.  It does get SUPER hot here at times, since the cliffs block the wind from getting in to cool you off.

If you’re looking to just chill at the beach, I don’t know that this is the most logical one in Santorini.  But if you want to get a glimpse of the dramatic beach, cliffs, and blue Aegean Sea together, this is definitely worth a stop in my opinion!

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Akrotiri Lighthouse

Akrotiri Lighthouse sits perched at the most southwestern tip of Santorini, giving it some of the best sunset views on the island (this is Nikos’s “local’s pick” for best sunset spot in Santorini).

The lighthouse itself isn’t terribly old, built in 1892.  I loved how the white building looked against the blue sky and even bluer water.

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There isn’t much to see or do here, so I didn’t spend a ton of time.  Some enterprising folks had brought a picnic lunch, which was smart.  I enjoyed the view for a few minutes and then moved on.

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Lunch at a local restaurant

And finally, lunch!!  Nikos took me to Kali Kardia (The Good Heart, also just locally known as “Anna’s Restaurant”), which sits up high on a ridge.  The dining room has a beautiful view, as a result.

Before I got to my meal, they had prepared a tray of samples from their homemade goods.  Attached to the restaurant is a small store with all sorts of products they make.  I sampled some olive tapenade, caper leaves, sun-dried tomatoes and tomato paste (Santorini is famous for its tomatoes), as well as a variety of jams and homemade wines.

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For my meal I went nuts.  I started with the local chloro cheese.  It’s a fresh Greek cheese made from goat’s milk in Santorini, characterized by a soft, creamy texture and a rich, distinctive flavor.  It’s quite hard to find, so when I saw it on the menu, I knew I had to try it.

Then I had stuffed zucchini flowers with rice inside, a piping hot moussaka, and then couldn’t pass up galactobureko for dessert.

I’ve given you tons of ideas for your own Santorini roadtrip, and hope that you take the time to explore the bottom half of the island if you’re planning a visit (including Santorini wineries).

This fascinating island has so much more to offer than just the famous bougie cliff hotels and crowded whitewashed streets of Oia (though those are great too)!

Other roadtrip explorations you’ll love:

• Exploring the Hill Towns of Northern Croatia
• A Day on Scotland’s Mystical Isle of Lewis & Harris
• Epic Road Trip Itinerary: A Guide To The Oregon Coast
• New Zealand Explorations: Nelson & Abel Tasman National Park
• Northern Israel: Caesarea, Tel-Megiddo, Sea of Galilee, & Akko

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