Destinations / Greece • Santorini

How To Explore Every Inch of Santorini in 3 Days

April 17, 2019

When my friends and I stepped off the ferry in Santorini at the port of Fira, the world came into sharper relief. Clumsily dragging my suitcase behind me, I gazed in wonder at the towering cliffs that surrounded us, white-washed buildings clustered along the edges and climbing up towards the bluest skies I’ve ever seen.

I didn’t know it at the time but I was in the cauldron-like hollow of the island called a caldera which forms following the evacuation of a magma reservoir. Meaning, when one of the largest volcanic eruptions happened in Santorini  around 3,600 years ago the centre collapsed and filled with water, forming the landscape that exists today.

As our local driver zipped along the narrow, winding streets up the caldera, he kept mentioning “Thira.” Nodding politely, I assumed he had a lisp and was referring to the capital, Fira.

So you can avoid looking like an utter idiot (like I did) Thira is the official name of Santorini. Why the capital and name of the island are so similar is beyond me.

Did the naming committee think it’d be cute if they rhymed like twins in matching outfits?

I’m sure there’s a reasonable explanation so if you find out what that is (history buffs: I’m looking at you!) let me know.


Descending the 1.000 stairs down the caldera to Ammoundi Bay



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Santorini is one of those rare places that is actually even MORE gloriously beautiful IRL than it is portrayed in glossy Hollywood films (and by “Hollywood films” I mean The Sisterhood of the Traveling Pants). When you think of the huge budgets of these movies, that’s quite an impressive feat.

You don’t need a lot of time to explore this island end to end, it just requires having a plan of action. From the overlooked Akrotiri to active Fira to quiet Oia, here’s an itinerary that will help you to explore every inch of Santorini in only 3 days:



Duration: 3 Days

Day 1:  Red Beach, Wine Tours, + Ruins in Akrotiri
Day 2: Fira Town, Argo Restaurant, + Sailing the Aegean Sea
Day 3: Admire beautiful Oia + Seafood feast in Ammoudi Bay

Day 1: Akrotiri

Overlooked in favour of the conveniently central Fira and idyllic Oia, the Akrotiri peninsula is mostly known for the famous ruins from the Minoan period. I’m not going to lie – I wasn’t planning on staying in Akrotiri until a random stroke of good luck resulted in a stay at a luxury villa but I’m so glad it did! It ended up being the most perfect day.

Read: When Bad Luck Turns Into A Stay At Adelante 88, A Luxury Villa in Santorini

Prehistoric Town of Akrotiri

Tucked away on the southernmost part of the island in the village of Akrotiri, this Bronze Age settlement was considered so sophisticated for the time that it’s rumoured to be the inspiration for Plato’s Atlantis. When the volcano that Santorini sits on erupted, the matter engulfed the Minoan town, preserving the buildings and its contents, leaving it largely intact. This is an ideal activity for history and architecture buffs.


Red Beach

Right up the street from the Prehistoric Town of Akrotiri is Santorini’s most unique beach. The saturated hills of the Red Beach is a striking sight, contrasting against the deep blue Aegean Sea and bright blue skies that are characteristic of Greece.

As you make your way down to the beach to soak up some vitamin D, make sure you keep your flip-flops on to protect your feet from the black and red pulverized volcano rock that the shore is comprised of.



Home-Cooked Meal at The Good Heart

This family-run taverna stands the middle of an open field, a calm oasis beyond the hustle and bustle of Fira and Oia.

Serving up traditional Greek cuisine – homemade with the freshest ingredients – revel in the cozy atmosphere at The Good Heart while dining on classics like dolmades (stuffed grape leaves) drenched in rich olive oil, taramasalata (salted and cured cod roe dip), stewed octopus and capers atop fava bean and roasted white eggplant, a rare product of Santorini soil.   

My favourites: taramasalata + dolmades!


Wine O’Clock

My favourite kind of history lesson is the kind that’s on wine and where better to educate myself than in one of the oldest wine-producing regions of the world – Greece!

The Santorini Wine Stories tour begins with a historical overview of regional winemaking at Koutsoyannopoulos Wine Museum – complete with audio tour and creepy mannequins demonstrating the various stages of wine production –immediately followed by a tasting in their cellars.

The next stop is Estate Argyros. Established in 1903, you’re welcomed into the expansive, all-white dining room at the winery and treated to a curated wine and cheese pairing while being educated on their vino.

The tour ends at the picturesque Venetsanos Winery just in time to catch the sun set in a wash of pastels over the island. From the prime vantage point on the edge of the caldera, leisurely savour the winery’s various vintages as the sky changes from dusky pink to deep purple.  


Geeked out over the pretty wine bottle labels for the Venetsano vintages!

P.S. The rosé was fantastic! Then again, I’m partial to rosé in the summer…so festive! 

Something our tour guide mentioned that I thought was really interesting was that every family on Santorini produces their own wine, whether for personal or commercial purposes. The warm climate and soil is ideal for wine grapes to flourish.

Fancy dinner at a local fav

Since you’re on this side of the island, take advantage of your proximity to where locals assert are the best restaurants in Santorini. Get the local/authentic experience at Metaxí Mas Taverna, specializing in Santorinean and Cretan cuisine. Or for a fancy night of fine dining, visit Selene in Pyrgos.

Day 2: Fira


Being the energetic capital of Santorini, Fira is a central hub that gives you access to amazing views of the caldera as well as to the islands best cafés, bars and nightlife. It has it’s own port from where you can take a cable car up from to catch your first glimpse of the island from above.


Bitter chocolate gelato from Zotti’s

Spend the morning exploring Fira town

If you like being in the middle of all the action, the capital of Santorini, Fira, is the place to be. Located on the top of a cliff of the caldera, you’re afforded dramatic views while you hastily devour a rapidly melting gelato for breakfast (like an adult!) and let your curiosity dictate which of the many winding alleyways to explore.


Amazing Meal at Argo

When you start to get distracted by hunger pangs, head to this multi-level alfresco restaurant. Built into the side of the mountain in Fira, Argo was one of the best restaurants I ate at my entire trip and that’s saying something.

Relax amid lush plants and magenta bougainvilleas before tucking into hearty fare – cheesy pastourmas, comforting veal and onion stifado (stew) served in tomato sauce on linguine (SO GOOD!), truffle risotto and crispy white eggplant that the island is known for.

From my favourite spot on any boat…right up at the front!

Day of Sailing On The Aegean

For a different perspective of Santorini, sail the turquoise waters in a luxury catamaran with VIP Sailing. Whether you choose the day of sunset sail you’ll be picked up from Ammoudi’s Bay for several hours of sunshine on the sea.

Lazily take in the sights – the Red Beach, Mesa Pigadia, Black Mountain, Indian’s Face Rock, the Hot Springs, Thirasia’s Port, etc…– as the captain, Dionysus (you can’t make this shit up!) provides historical snippets of the landscape. Work up an appetite cannonballing off of the side of the boat before feasting on prawn linguine, Greek salad, baked Plevrotous mushrooms, fava beans and octopus as the vessel basks in the fading light.



Cocktail Hour

While you may be exhausted after a jam-packed day out on the Aegean Sea, seize the night because it’d be a shame to miss out on the lively Fira nightlife. Throw on your least wrinkled outfit and head to PK Cocktail Bar to sip a fancy concoction under the stars while marvelling at the twinkling lights of the caldera.

Locals also suggested Tango for a more club/party experience or Two Brothers Bar which will bring you back to your university  rager days.


Growing up reading Asterix comics, I always related to Obelix’s constant hunger.

Late Night Gyros

To satisfy the midnight munchies, swing by Obelix (named after a gluttonous French cartoon character), said to be one of the best spots to grab a gyro in Fira. While the menu was extensive, I stuck to the classic pork gyro – juicy tomato slices, red onion, thick cut fries wrapped in grilled pita with a generous dollop of garlicky tzatziki (ask for extra!).

Day 3: Oia

If Fira is for the party people, Oia is the romantic haven for newlyweds, couples and families to enjoy the charm of the most infamous Cycladic island. Meander through the (relatively) quiet streets (minus hoards of Asian tourist from docked day cruises) lined with white-washed buildings and find a prime spot to enjoy the incomparable sunsets.


Hike from Fira to Oia

The best part about Santorini is the incredible views from the edge of the caldera. To avoid the intense heat, aim to hike either early in the morning or around sunset. Bonus is that you’ll capture the best photos since that’s when the light is most magical.

Breakfast Break at Cafe Galini

Give your feet a break and refuel for the bulk of the hike to Oia on the terrace at Galini Cafe for the most spectacular view (are you sensing a theme? Where isn’t there an amazing view?!). Hidden away in a fancy hotel in Firostefani,

Explore the beautiful nooks & crannies of Oia

Oia (pronounced “e-yaah”) is one of those rare places that look just as beautiful IRL (if not more) as it does on Pinterest. Take your time wandering the white and pastel streets and posing for pictures at every corner and cerulean domed church.

I particularly loved poking around the charming shop, Atlantis Books.


Grab dessert from Skiza

Drool over the glass display at Skiza Cafe featuring a delectable array of desserts before grabbing a spot overlooking the caldera on the upper level.

Cheers with the local Santorini beer (Yellow Donkey) and nosh on a light salad or a savoury crepe before satisfying your sweet tooth with a Vin Santo (sweet Greek dessert wine) millefeuille. The pastry was so flaky and the cream so light that I still dream about it!

OMG, vin santo millefeuille…soo good!

Jump Off Ammoudi Bay

Watch your step! It’s all fun + games until you step into a pile of donkey poop.

After the sweaty hike from Fira, cool off by taking a refreshing dip in Ammoudi Bay. Avoid all the donkey 💩while descending the 1,000-step staircase and keep to the left of the cliff face to reach the perfect spot to dive into the crystal clear Mediterranean waters.

If you’re daring, climb the massive boulder to jump off of! Afterward, slather on some sunscreen before working on your tan.

Sunset Dinner @ Dmitris Ammoudi Tavern

Santorini is famous for unforgettable sunsets, views of the caldera and fresh seafood and Dimitris Ammoudi Taverna combines all three. Make a reservation in advance for dinner to snag one of the coveted tables by the water. You’ll be grateful for the unhindered views of the sunset.

Dig into freshly caught sardines and octopus, tomatokeftedes (fried tomato fritters) served with a creamy dip, and a satisfying dish of fava with capers for an authentic Greek feast.

Whether you have 3 days or 3 months, you’ll never have enough time in the most renown of the Greek Islands. Just drink as much of Santorini while you can and count yourself lucky for the experience.

If you’re looking for a place to stay in Santorini, this luxury villa will blow your mind!

Keep your stalking game strong and follow me @teriaki if you aren’t already!