Our Santorini itinerary and magical island moments

Trying to find a Santorini itinerary for 3, 4, 5, or more days or want to know how many days to spend on the island? We were like that before going to Santorini. But then, after some research, we decided to go with the flow and be flexible and see what moments we would experience.

One week was not enough to give a proper time for encounters with all the places to visit on Santorini, but we’ve got a good glimpse of the fava island and its dry landscapes and rich culture. Every place was a special moment, and now we’re going to recap Santorini’s magic for you.

Landscapes in Santorini, Greece

Oia

During our first time on Santorini, which lasted less than a day, we mostly experienced Oia. Now it was time to give it enough time, to browse the village streets and whitewashed houses carved into the rugged clifftops, and to absorb views over the vast caldera filled with deep-blue water. Getting lost on narrow alleys and staircases without knowing if we entered another killer-view hotel property or not, finding the best way to take photos (responsibly!) of the blue domes, and making use of our sunglasses to protect our eyes from sparkling white under the scorching sun – that’s some of the charms of Santorini!

If you love books and reading, we suggest you head to Atlantis Books and dive into one of the most fascinating bookstores on Earth! There’s a boutique choice of old and original editions of world-known books, as well as a varied choice of new and modern books in more than 10 languages. Even if you don’t buy anything, you can hang out and talk with the bookseller.

Atlantis Books, Oia, Santorini, Greece

Amoudi Bay

Reached by foot via the 200 stairs from Oia or by car, Ormos Ammoudi welcomes you with delicious taverns overlooking the sunset, nice yachts for your sailing journey, and the nearby rocks for adventurous cliff diving. It’s a picturesque place right under the red rocks and white Oia.

Ammoudi Bay, Santorini, Greece

Vourvoulous beach

After the streets of Oia became unbearable to walk on and all the ice cream didn’t motivate us to keep going, we decided to retreat to a beach. And that’s how we found Vourvoulous beach. It’s a bit isolated and lesser-known, the wind can be strong and the waves too big for swimming, but it’s the perfect place to relax and sunbathe with the black pebbles and the turquoise waters.

Vourvoulous beach, Santorini, Greece

Sunset from Castro, or Oia Castle

Our local host confirmed that the best sunset spot in Oia is Oia castle or Castro. We ventured towards the old castle 1.5 – 2 hours before sunset and all the wait was worth it. Seeing the magical colors of Oia, the sunrays caressing your face, and the darkening caldera – those are moments that are easy to capture in your mind.

Thira

Thira, or Fira, is the capital of Santorini. Getting lost in the quaint cobbled streets, weaving through the cultural and commercial center of the island, is a must-do experience. If you’re lucky, you’ll stumble upon doors leading to open-air terraces with majestic views, beautiful church domes, and The Three Bells of Fira. Pay attention to little details like trees and bushes in blossom taking different shapes, the pretty local shops full of white-and-blue enchanting dresses fluttering under the soft breeze, and the sparkling cobbles reflecting the particles of sunshine.

Thira nightlife is a magnet for those seeking fun after dark. We improvised a bar-hopping session trying to find a bar that could fit us with not-so-loud but loud enough music, enough free space, and air to breathe. After a long time of lockdowns, restrictions, curfews, and whatnot, the nightlife scene in Thira was emerging as a gulp of air.

Santorini Old Harbor

Dare to walk down the more than 500 steps to the old harbor of Santorini, called Ormos Firon. You can absorb the views towards the caldera and up to Fira itself. If you don’t feel like taking the stairs (up or down or in both directions), please don’t use the poor donkeys and mules, just take the cable car. At the harbor, boats and ferries are there to take you around the archipelago, and taverns and a market are waiting to entertain you.

Sunrise at Perissa beach

Following the tradition to celebrate July Morning, we headed to the famous black Perissa beach at night. We could feel the perfectly shaped pebbles under our bare feet, the fresh and calm sea inviting us for a morning dip (swimming suits not necessary), and the first July rays of sunshine emerging from the water after a whole night of a private party. We knew we had to come back for more of this.

Sunrise at Perissa beach, Santorini, Greece

Catamaran cruise

The catamaran cruise around Santorini was one of our top 5 relaxing and recharging experiences, hands down. Here is the route we took with captain Petros:

Vlichada – Red beach – White beach – Akrotiri Lighthouse – Palea Kameni – Hot Springs – beautiful sunset over the caldera

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Here’s the link to the Santorini Catamaran Cruise with Lunch & Open Bar tour we took and highly recommend!

Megalochori village

We got to Megalochori village early enough to drive through the narrow cobbled streets, explore a cave house, and enjoy the white bell towers reflecting the sun. After we’ve absorbed enough of the village’s magic and sunshine, we decided to take a break and enjoy a delicious breakfast under the vine trellis.

Megalochori village, Santorini, Greece

Emporio village

Emporio welcomed us with winding medieval alleys leading us to the restored 15th-century Venetian Castle. Getting lost was the easiest task, and even steep staircases would only take us to almost intruding private houses. It was almost mid-day and the heat wouldn’t allow us to get lost once more, so we headed back to the tangled alleys with white-washed walls.

Emporio village, Santorini, Greece

Exo Gonia

Our shortstop in Exo Gonia was to contemplate a blue-domed Orthodox church and the view of the sea in the background. Shortly after that, we headed on a quest to find a place that opened early enough for lunch.

Exo Gonia, Santorini, Greece

Kamari beach

Kamari beach is a volcanic black sand and pebble beach, overlooked by Mesa Vouno Mountain. While there were enough tavernas and bars to satisfy our hunger and thirst, we also enjoyed the view of landing airplanes, coming close enough so you can take a good photo of the flying beasts. On the other hand, Kamari is famous for the souvlaki cafes, Irish pubs, and the party noise, if that’s what you’re looking for.

Kamari beach, Santorini, Greece

Imerovigli

We found in Imerovigli what we felt to be the peaceful Santorini vibe. The clifftop village offers mesmerizing views of the caldera and its islands, some beautiful white terraces, home to upscale hotels and fine-dining restaurants. We decided to pamper ourselves with dinner in one of the restaurants with the best sunset views and not only did we have one of the most beautiful and secluded sunsets on the island, but we also had great food at a very affordable price. The name of the place is Infinity Restaurant, it is located in Tholos Resort.

We would definitely return to Imerovigli and if we decide to treat ourselves to a stay at a cave hotel with a million-dollar view, we would consider Imerovigli before Oia.

The Greek Wedding

If you have friends and family in Greece, maybe you’ll get invited to a Greek wedding someday. You will experience traditions, great food and wine, chatting with friends, keeping up with the relatives, dancing and singing at the wedding, you might even break some plates. This will be an experiential immersion of the highest level, one of the main reasons to travel and explore.

If you don’t have wedding invitations in your mailbox, you must go to the Greek Wedding Show in Thira while you’re in Santorini. Yamas and let us know how it went. Here’s the link to book your ticket for The Greek Wedding Show in Fira.

Pyrgos

Surrounded by vineyards producing renowned Assyrtiko white wines, we knew Pyrgos will be the best choice to stay during our trip to Santorini. When we explored its steep, medieval alleys passing wine bars, tavernas, galleries, and boutiques we had the feeling we’ve traveled to the past. Gentle bouzouki music was flowing in the alleys, accompanying the view of pretty much all of Santorini. We stopped to chat with a local shop owner and time stopped as well. It was magical to explore one of the towns attracting many more locals than tourists.

Pyrgos, Santorini, Greece

Perivolos beach

It’s impossible to tell where Perissa beach ends and where Perivolos beach starts. It is quite easy and possible to enjoy the black sand with just the perfect size to comfortably walk on without sticking to your feet. Visiting in the daytime was another exciting experience – playing with the waves, hiding from the sun, and enjoying the relaxed vibes.

Art Space Winery

As the name suggests, Art Space Winery is not only an old winery with chambers carved into the pumice rock, but it’s also a center for works of art from the sphere of painting and sculpture by Greek and international artists. We had a wonderful walking tour around the cave chambers, which then turned into a world-class wine tasting. We fell more and more in love with Santorini by drinking the Vinsanto, Assyrtiko, Nychteri, Aidani, and Mavrotragano wines. The winery still uses traditional wine-making techniques.

Art Space Winery, Santorini, Greece

Akrotiri Lighthouse

One of the oldest lighthouses in Greece, Akrotiri Lighthouse is nowadays famous for its breathtaking sunset views. For one of those, we headed to the lighthouse, and even though many had done the same, there was enough magic for all of us! If you want to enjoy even a better view, go up the hill that’s right next to the lighthouse. It will open the view even more.

Akrotiri Lighthouse, Santorini, Greece

Akrotiri Archaeological Site

The only historical museum we visited on Santorini was the prehistoric city of Akrotiri. The Cycladic Bronze Age settlement was destroyed in the Theran eruption in the 16th century BC and buried in volcanic ash. That’s how many of the frescoes, objects, and artworks were preserved. The Akrotiri Archaeological Site features an excavation of part of what used to be a fisher and farming village. It’s lovely to walk around and explore the different layers and objects preserved, however, be sure to read about the place in advance or get a guide as there aren’t many informative signs and labels.

Akrotiri Archaeological Site, Santorini, Greece

Wine Museum / The Koutsoyannopoulos Winery

The Koutsoyannopoulos family created an entertaining wine museum in a cave 8 meters below ground and 300 meters long. You follow the wine road through different chambers demonstrating the wine-making process, and different facilities used in time, and gaining knowledge of the divine drink and its history on the island.

The tour ends with a wine tasting where you can choose different packages according to your taste and budget. While we enjoyed the wine cave, the wine tasting had a bit too mass-tourism vibe.

Wine Museum, Santorini, Greece

Paralia Karterados

After too much wine, we decided to chill on the beach. We found the small Karterados beach, which offered a beach bar with views of airplanes landing just behind the corner. The sea was again a bit rough, but it was so nice to watch birds circling around ships in the endless blue.

Santo Wines

For our last dinner and sunset on Santorini, we chose Santo Wines – a winery with a scenic terrace offering epic caldera views. The restaurant had several winetasting packages to choose from, paired with the right meze and a-la-carte food. I really love the fact that with your wines arrives a booklet to assist you in appreciating them and taking your own notes on the samples. Even if you’re not a wine aficionado, visit Santo Wines for the majestic views and the serene experience.

Santo Wines, Santorini, Greece

Prophet Elias Monastery and Lookout Point

We drove almost all the way up to the highest point to see all of Santorini. You can walk around the Prophet Elias Monastery, buy some of the local produce there, and take in the view from above. There is a nice spot by the road where you can sit on a cement fence and watch airplanes landing and taking off.

Prophet Elias Monastery and Lookout Point, Santorini, Greece

Messaria

We decided to go to Messaria for our last lunch in Santorini. We found Pentozali tavern on Google and that was the perfect ending to our one-week itinerary on the island. Two people from Crete opened the tavern near the school in Messaria, where you’ll most probably sit outside under the shade of eucalyptuses. The menu includes potato salad, cheese served with thyme, feta with olive oil and oregano, Cretan rye rusks, and daily freshly cooked dishes which will make you lick your fingers. Don’t forget to try the local beers, barrel wine, and aromatic raki.

Landscapes in Santorini, Greece

Where to stay on Santorini

We couldn’t recommend Ampelos Executive Houses in the outskirts of Pyrgos more! The cave houses can host up to 5 people, have gorgeous views of the vineyards, and are high enough so you can look around and see lots of Santorini. There are kitchen and dining areas (one inside and one outside the houses), and air-conditioning (which is crucial, especially in summer). Pyrgos is a great starting point to explore the whole island. And the host Manos will go beyond to make sure you have a great stay. Thank you for the bougatsa, Manos!

View from cave house in Pyrgos, Santorini, Greece

Eating out on the island

We decided to share a list of the restaurants that we really loved. We believe those places can enrich your experiences on the island.

Food and drinks of Santorini, Greece

Renting a car on Santorini

As for most of our trips to different parts of Greece, we booked our car with Rentalcars.com (sometimes we go in our car if we travel by ferry – check for tickets here). We got a car of the exact size we wanted, with many scratches from previous drivers but nothing serious. The rental company provided a great service full of trust (they just told us to leave the car and the keys in a parking lot when we were leaving), just like that. We had no issues with the car, no accidents. If you want to be flexible and have enough freedom to explore any part of the island on your itinerary in Santorini, we recommend renting a car.

Landscapes in Santorini, Greece

We hope Santorini put its spell on you through our words, photos, and magical moments. Let us know if you have any questions about your Santorini itinerary and things to do!

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