Kalimera Santorini: 3 Days on a Greek Island

Laura Burgess is a Raleigh, NC native who embarked on a solo-trip all around Europe in 2015. Last year she spent 3 months on the island of Santorini and fell in love with the country and its people. It drew her back and now she is living their full time! Laura shared with DT365 her favorite itinerary and told us if she could visit Santorini for the first time again, this is what she would do! Check out Laura's Instagram to keep up with her time in Santorini @laurahamburgers.

Tripper Tips:

In the summer, the days are hot and sunny, but don’t be surprised if it gets a bit chilly at night.  Make sure to pack a sweater.  If you’re visiting the island in the spring or fall, you never know what the weather will do, so a raincoat is also essential.  Winter is not an ideal time to visit Santorini.

Laura told us that a highlight of her time on Santorini was joining Santorini Walking Tours on a week trip to 3 different islands, Amorgos, Naxos, and Iraklia. “Nikos guided a few people for the week and I went along to photograph--it was the most amazing experience. It's interesting to see the different islands and how each one is so unique. Greece is really a special place. “

Info: Santorini in Greece is a picturesque island, known for its spectacular beauty, its famous caldera, and plenty of sun and black sand.  The island itself was created from a massive volcanic eruption long ago, and the magnificent views you see in pictures are of the actual caldera of the volcano.  As you explore this enchanting island from every angle, you will be astonished at the whitewashed villages and vibrant colors of its wildlife. It’s a fascinating place with rich history and special cultural traditions, like wine production and how they make their cherry tomatoes so delicious!  Every Greek is proud to share a few stories and history of the Papadopoulos family, and will most likely invite you into their home at some point. This Cycladic Island is perfect for those looking for a bit of everything from shopping, to eating, to drinking, to being active.

Getting There: To get to Santorini, you will most likely fly into Athens and then hop on a ferry from the port of Piraeus.  The Blue Star ferry takes about seven hours, but with sea and island views the whole way there, it’s not too bad.  If you’re in a hurry to jumpstart your vacation, I recommend taking the Ryanair or Aegean flight, which takes about 45 minutes.

Where to Stay:  Choose a villa or suite on the caldera in Firostefani or Imerovigli. The villas don’t come cheap, but most come with a pool, a chef to make your breakfast, and a terrace to take in some of the most awe-inspiring views in the world.  These two neighborhoods of Santorini are next to each other and are only about a 20-minute walk to the center of Firá.  They are a bit quieter and offer guests a chance to relax just off the main path. Most celebs opt to stay in Imerovigli. A few excellent options are Santorini Perfect Villas, Altana Traditional Houses and Suites, and Med Villas. If you prefer to stay in a boutique hotel good choices include: Iconic Santorini, The Grace Hotel and Hotel Galini. Want to base yourself in Oia? Laura recommends Andronis and Esperas, two small boutique hotels.

How to Get Around: The main bus stop in Firá offers buses to the beaches, popular sites, and Oia (make sure you pronounce it correctly “EE-a” or the Greeks will make fun of you).  The bus system is not the fastest, but it does get you from point A to point B.  Just keep in mind if you wish to see more in less time, a better option would be to rent a car, which most tourists do at some point. (Or for the more daring an ATV) It’s a fun way to get around and you’re able to see more of the secluded spots that the buses don’t necessarily go to.  

Day 1

8:00 am: Walk to Firá and grab a fredo espresso (iced espresso) and a pastry at the bakery in the main square. The fredo espressos are some of the best in the region and it’s a perfect way to start a busy day. 

9:00 am: Meet your tour guide in the center of Firá who will take you on a walk of a lifetime.  Santorini Walking Tours offers four walking tours, but a must-see is the Firá to Oia Caldera hike.  You won’t be disappointed, trust me.  Details here.

1:00 pm: After you finish your walking tour, you will have landed in Oia, the colorful, boutique-y village that is one of the prettiest spots in Santorini. Definitely spend some time here eating, shopping, and exploring all the cobbled secret passageways.  Have lunch on the terrace at Melitini and enjoy more caldera views while you sit back and enjoy a nice mezze, aka tapas, style lunch and of course, a glass of wine.

3:00 pm: Oia is the place to shop with plenty of boutiques offering women’s contemporary fashion, jewelry, and artwork. Check out the world famous Atlantis Books and AK Gallery, two don’t miss stops while you are there.

6:00 pm: Grab an ice cream and head down to Katharos beach in Oia just in time for a mini-siesta and to watch the applause worthy sunset.  Katharos beach is my favorite place to watch because it’s peaceful and away from the “sunset crowd.” If you wish to be a part of the crowd, go towards the windmill and grab a seat anywhere.  As the sun sets, you will hear lots of applause.  It’s silly, but it makes me smile every time.

8:30 pm: Once the sun goes down, you will probably be tempted to head back to Firá, but I recommend staying in Oia just a bit longer and grabbing a drink at MaryKay’s bar, which is right across from Atlantis Books.  They have excellent cocktails and always offer a little snack to hold you over until dinner. The buses back to Firá are chaotic and crowded just after sunset so it’s optimal to sip a tasty beverage while you wait for the crowds to disperse.

9:30 pm: Catch the bus back to Firá and head towards the main square.  Do as the locals do and grab a souvlaki and Yellow Donkey beer while you sit on the benches and people watch.  The square is always buzzing with activity and you just can’t beat Greek souvlaki! 

Day 2

9:00 am:  Enjoy your Greek coffee and hearty breakfast at your villa on the terrace and then rent an ATV.  Contact Vazaios and have your ride delivered right to you. 

10:00 am: Make sure to take a map with you and head towards the black sand beach for some well-deserved relaxation.  Go to Seaside by Notos at Perivolos and grab a lounger on the beach.  Order a fredo espresso or a cocktail if you are feeling good and take in the beautiful beach views.  Go for a swim or a walk down to Perissa beach and see the many beachside bars, tavernas, and interesting people on this side of the island.

12:30 pm: Hop back on your ride and go to Santorini Arts Factory (SAF) and explore what was once an old tomato factory.  Half of the factory is a host to an industrial museum and the other half is dedicated to performances, concerts, and events.  Check out their website for full details of everything they have to offer.

2:00 pm: After exploring SAF, go to To Psaraki for lunch. Their specialty is fresh seafood, which pairs nicely with a glass of assyrtiko, a local exquisite wine from Santorini.  Have a couple of glasses and let the excellent staff take care of you for a laid-back lunch. 

4:00 pm:  To digest properly, you will want to head down to Vlychada beach for the warm afternoon sun.  Lay your towel on the sand and let a few hours melt away with pleasure.

6:00 pm: On the way back to Firá, stop at one of the many ceramics shops and see the beautiful handcrafted pieces of pottery.  One of my favorites is 1260 Ceramic Studio.

7:00 pm: Sunset in Santorini is spectacularly unique and must be viewed every night you are on the island. Go to Venetsanos Winery for a tasting of their delicious wines while overlooking the caldera.  Order a cheese plate to go along with the evening’s drinks. This place never disappoints.

9:00 pm: Head back to your villa for a quick shower and to park your rental for the night. Once you are finished getting ready, walk to one of the oldest establishments of Firostefani, Aktaion Restaurant.  This dinner spot is a favorite among the locals so you know it will be fresh, filling, and flavorful.

11:00 pm: Your night isn’t over at dinner because a trip to Santorini wouldn’t be complete without going out in the center of Firá.  Walk through the streets and take in the sounds of Santorini’s exciting nightlife.  Go to Kira Thira Jazz Bar for your first drink, then to Tropical Bar towards the caldera for a few more, and end your night at Calderaki, a modern dance club.

Day 3

9:00 am:  Views of the caldera are reason enough to wake up early in the morning, but Greek coffee is a close second.  Definitely take advantage of the villa’s breakfast and your personal terrace.  After breakfast, drive down to Akrotiri and the red beach. 

10:00 am: You will see signs pointing you in the right direction, which will take you on a short walk to the red beach.  Enjoy the contrasting colors of the red rock, black sand, and turquoise water and then walk down the path to go for a cool dip in the Aegean Sea.  Beware of the sign warning you of falling rocks so choose your spot on the sand wisely.

11:00 am: While you’re in this area, explore the Archaeological Site of Akrotiri, a must-see in Santorini to learn about the advanced prehistoric civilization, which inspired the myth of Atlantis.  It was a nation who vanished in the super volcano over 3,000 years ago.  If you wish to gain the most out of this experience, a guided tour is recommended. 

1:00 pm: Head towards the water and on your right, have lunch at The Cave of Nikolas for authentic Greek cuisine. If you are lucky, you will get to meet the owner, Nikolas, who will share his old stories of being a fisherman back in his day.  If you are really lucky, he will tell you the story of how he discovered a fully preserved kori statue.

3:00 pm: Go for a mid-afternoon walk through the quaint village of Pyrgos.  This is a traditional Greek village and home to Kasteli, the castle of Pyrgos.  Explore the inside, narrow alleyways, and interesting Greek homes.  Before you leave, make sure to order a raki, a traditional grappa drink, at Kantouni Restaurant in the main square.

5:00 pm: I recommend ending the day with a walk to the rock of Skaros, which is off the main path in Imerovigli. This walk is not for the faint of heart, but it offers some stunning views of the island. 

6:30 pm: Have an early dinner in Imerovigli with a nice bottle of Santorini wine.  Go to Aegeon Restaurant to watch one last sunset overlooking the caldera and reflect on your amazing time on the this Greek island.  

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