windmills astypalaia greece

The Perfect Two Week Travel Itinerary For Greece

Greece is without a doubt my favorite country in Europe. The combination of its fascinating ancient history, beautiful ruins, stunning beaches, and the most picturesque islands with its white house blue door combination makes it the ultimate travel destination.

180 degree sunset bar mykonos
Or you can blow your entire budget at a place like this in Mykonos that comesm with €18 cocktails

I’ve traveled extensively throughout Greece from the Cyclades islands, Ionian Islands, Athens, the north of Greece and more so I think I’m perfectly fit to help plan the two week Greece trip of your dreams.

Greece is not a big country by land mass but it packs an absolute punch with the amount of places to visit. Whether you’re a history buff wanting to soak in the ancients sights of Athens, or a beach bum with dreams of searing blue beaches, there is something for everyone. Greece is a magical place and two weeks is simply not enough to see everything.

Nevertheless, I will help you with your trip as much as I can so you can get the highlights and then start planning your trip back to this beautiful country!

Traveling in 2023: Note that I suspect tourism and crowds to be monstrous in the summer 2023 season. Book well in advance and prepare yourself for huge crowds of tourists coming from America and China. If possible, plan your trip from mid September onwards!

Table Of Contents show

Where to go in Greece for two weeks

Again, two weeks in Greece is simply not enough to see the whole country so you’ll have to be strategic with where you go. For the purpose of this itinerary, I’ll give multiple options of how to plan your trip.

Monastiraki A for Athens rooftop bar view of Acropolis

The most popular destinations in Greece are in the Cyclades islands. These islands are some of my favorite places to travel in the world. Famous for their famous and impossibly picturesque white houses with blue window frames, the Cyclades is a must visit in my opinion.

Naxos Chora
Naxos Chora

In addition, I think you should also see the north of Greece as having two weeks will allow you to mix things up a bit. The north of Greece is far different than the islands. The mountains are absolutely stunning and the vibe is distinctively more Balkan like the countries north of Greece (Bulgaria, Macedonia etc.)

With a two week itinerary to travel through Greece, I would recommend starting off in Athens and then venturing north to visiting two Cyclades islands. You don’t want to rush your trip through Greece because it’s all about enjoying your time and going slowly with the Greek way, aka eating amazing food, sipping on wines with views of the Aegean, exploring the nature side of the islands, and simply relaxing.

My other Greece Posts

I’ve spent extensive time traveling through Greece so make sure to read my other Greece related posts!

How to travel between the islands?

Well there is no island hopping without a way to get between the islands. Thankfully, Greece has one of its most extensive and serviced ferry system in the Cyclades.

Ferries are the only way to get between islands. In the summer months, they run frequently with multiple ferries coming into an island per day. There are multiple companies to choose from which is great for keeping costs reasonable.

zante ferry
Ferries in the Cyclades

Some of the most popular islands have airports like Mykonos, Santorini, Milos, Naxos etc. where you can fly into from Athens or international destinations. However, there are no flight routes (that I know of) between the islands, so you will not find any flight between Mykonos and Santorini. This is because the distances are so short that flights don’t make sense as well as there being an extensive ferry system to cover this.

Ferries in the Cyclades are generally quite big ships and are very comfortable. I took ten of them so I’ve experienced all different types of boats and for the most part, I am pretty satisfied. Most ferries start from Athens and make a route where they stop at different islands. You are essentially hopping on and hopping off depending on your point of origin and destination.

There’s so much to know about the Greek ferry system that I’ve written an entire post dedicated to this topic. Make sure to read that so you know what to expect when you arrive!

Is two weeks enough time to visit Greece?

Two weeks, or 14-16 days is a good amount of time to see the highlights of Greece. However, there is simply way too much to see in Greece for you to see so much. I spent two months traveling the Cyclades islands alone and that is just one group of islands among many!

With two weeks in Greece, I would recommend focusing on Athens and the Cyclades island chain. If you’re feeling like you want to be more active, then I would definitely combine it with a 2 night trip to Meteora. I am a big proponent of visiting the capital city of Greece but I know that want to skip the big city and go straight for the islands. My rule of thumb is to spend 3-4 days per island just so you can have ample time to explore and relax. 2 days is too rushed and just the logistics of getting into an island by ferry will eat up your free time.

Therefore, if you are combining with Athens and Meteora, I would choose two to three islands to finish out the trip.

Two weeks in Greece – Day 1-3: Athens

The ancient capital of Greece is the first stop on the 2 week Greece itinerary. It’s likely you’ll fly into Athens and it would be a total shame to skip the city if you’re already here. The city is not only chalk full of famous historical sights but it is just an amazing city with so many amazing restaurants and bars.

I would recommend at least 2-3 nights in Athens to get the proper experience. With two weeks in Greece, this will not be a problem. I’ve spent extended time in this city so I know there is plenty to offer for those that want to stay longer but 2-3 days is enough for a tourist trip.

For a list of everything to do in Athens, make sure to read my What to do in Athens guide. Here is a summary of a few of the top highlights you must do while you’re in Athens!

  • Acropolis
  • Acropolis Museum
  • Ancient Roman Agora
  • Hadrian’s Arch
  • Temple of Zeus
  • National History Museum
  • Lycabettus Hill
  • Walk around Monastiraki
  • Temple of Poseiden day trip


Without a doubt, the main sight of interest in Athens will be the Acropolis. This is one of the original seven wonders of the world and is one of the most well preserved ancient Greek monuments in the world.

The name Acropolis is Greek for the highest point in the city (Akro means high, and polis means city). Essentially, every town in Greece has an Acropolis because it is just the highest point in the town but of course Athens is a bit more famous than that.

The Acropolis consists of the Parthenon which is the iconic ancient Greek temple that is pretty much the only picture necessary to describe Greece, various other temples, and theaters. It’s very impressive and will check off all the boxes for your Ancient Greek fix. However, in the end, I’d still say the Pyramids of Giza were much more impressive.

Temple of NIke in Athens
Temple of Nike

You can spend a lot of time here depending on how into the history you are but generally I think 1-2 hours is enough. During the summers, you can expect a large crowd at all times of the day. The best way to avoid the crowds is to come here in the very early morning or stay until it closes.


It’s hard to take a bad photo here so shoot away!

Admission Cost: €20 in the summer months, €10 between Nov and Apr
Opening Hours: Monday to Sunday From 8am to 8pm
*You can purchase the Athens Pass for €30 which will allow you to visit numerous sights in Athens including the Acropolis. Definitely worth it if you plan to do most things.

Roman Agora

The Agora, while not in the Acropolis, is a must visit sight as well. It’s the most well preserved Ancient Greek temple in all of Greece. After seeing the Acropolis which is almost half gone, the Agora offered a glimpse of what these buildings looked like fully standing.

Temple of Agora Athens
Temple of Agora
Temple of Agora Athens
Temple of Agora Athens

The Agora, translating to “a place of gathering”, was once dotted with statues, shops, markets, schools and it was the place Socrates used to lecture his young disciples.

The whole complex only takes about 20 minutes to see but is well worth the visit especially if you’ve purchased the Athens Pass.

Visit the Plaka and Anafiotika

The most unique part of Athens has to be the Anafiotika neighborhood. This neighborhood is located right at the base of the Acropolis with perfect views over the city. It features houses built in the traditional Cycladic style that you’ll find on beautiful islands like Mykonos and Santorini.

24 Hours in Athens: A City Beyond the Acropolis

I love the Cyclades and everything about the islands so what a surprise it was when I could find the iconic white stone houses in the middle of Athens! In the early 19th century, King Othon hired the best builders from Greece to refurbish his palace. These builders came from the Cyclades and from the island of Anafi (hence the name). The king let the builders stay at gifted them land nearby to the Acropolis where they build homes for their families in the traditional style.

You can find the neighborhood high up in the Plaka district of Athens and it’s the perfect place for some nice photo opportunities. You’ll have to walk through Plaka to get to the Anafiotika neighborhood. Along the way, stop for a quick coffee on the idyllic steps of the Plaka at Klepsýdra or Dióskouroi and soak in the Athens air.

Enjoy rooftop drinks with views of the Acropolis

For golden hour, head to one of the many rooftops in Athens with beautiful views of the Acropolis. This is one of my favorite things to do in Athens as I think the view is absolutely beautiful.

Monastiraki A for Athens rooftop bar view of Acropolis

The best bars to do this are A For Athens and Couleur Locale. Both bars serve great drinks with a laid back vibe looking out at the Acropolis.

Dinner in the city

Finally, to end a great day, enjoy a delicious dinner of Greek food out in the city. There are countless Greek restaurants in Athens ranging from local but vibrant restaurants to upscale and fancy. Monastiraki and Psyri have endless restaurant options for you to choose from.

Head over to a place like Lithos Taverna, Bandiera, or Maiandros and feast away. Greek food is known for its fresh ingredients, generous portions, and delicious flavors. It’s very easy to overdo it because you want to try everything.

If you still have energy after dinner, go enjoy a cocktail at one of the world ranked cocktail bars at places like Baba Au Rum or the Clumsies!

Blue aegean negroni clumsies bar athens
The famous aegean negroni

Odeon Theatre Show

If you are visiting in the summer, make sure to book a show at the Odeon Amphitheatre which was one of my favorite things in Athens.

Odeon theater
Seeing a show at the Odeon!

Free Walking Tour

I’m a big fan of free walking tours in cities and Athens is no different. The free walking tour I did here was incredibly informative and I learned things that I definitely would not have learned if I hadn’t gone.

changing of the guards
watching the changing of the guards in athens

We walked by all the main sights and got lots of stories from the guide about Greek culture, history, and food. We even visited a neighborhood adjacent to the Acropolis that is a little mini Cyclades within the city. I had no idea this existed but really it felt like I was walking through a village in Milos. This is because builders from the Cyclades were known to be the best and were brought in to construct a lot of the official buildings back in the day. They settled near to the Acropolis and were allowed to build in whatever fashion they wanted.

Athens main market
Visiting the main Athens fish market

Olympic Stadium

Olympic stadium athens

I had totally forgotten Athens was the home for the 2004 Olympics (and of course the original Olympics). They built this giant stadium modeled in the traditional sense for the opening and closing ceremonies in 2004.

It has since been largely unused and just a relic from that those games. I’m not sure why they wouldn’t use such a beautiful structure but I guess it’s the same reason they don’t want to reconstruct any of the Ancient buildings?

Nevertheless, it’s largely just a giant stadium in the middle of the city nowadays that tourists can visit. It is €5 for the entrance fee and you can walk around the stadium to your desire. There weren’t many visitors at all during the times I visited so you can bet on taking some fantastic photos.

Mount Lycabettus

Don’t miss a visit to Mount Lycabettus which is the ultimate sunset spot in my opinion. It’s near to the city center and can easily be reached by foot or taxi. You can either take a cable car from the entrance for €5 or walk yourself to the peak. From the entrance of the cable car, it is only about 200m to the top and is not a difficult hike.

Mount Lycabettus Athens
Views for days
mount lycabettus

The views here are simply stunning as you can really grasp just how massive of a city Athens is. You can even see the Mediterranean from the viewpoint.

There is a cafe and restaurant here where you can buy cocktails to enjoy the view. The restaurant is very expensive but could be worth it if you’re keen for some nice views!

Two Weeks in Greece – Day 3-5: Meteora

From Athens, the next stop on the trip is a visit to the holy monasteries of Meteora. Meteora is one of the most naturally beautiful places in Greece, and is vastly different than the islands in the south. This goes to show just how diverse and unique of a country Greece is.

How to get to Meteora from Athens

There are daily bus services from Thessaloniki and Athens to Meteora. These buses are not direct but go via Trikala. This means that you have to go from Athens to Trikala and then take another bus to Kalambaka. Buses depart from Trikala to Kalambaka almost every hour. From Kalambaka, you can go to the Monasteries of Meteora by taxi or by bus (bus works only in summertime).

The bus from Athens to Trikala/Kalambaka departs from Liossion KTEL Bus Station. To go there, passengers have to take the metro line to Attiki Station and then take the bus/taxi to KTEL Liossion. The walking time from Attiki to KTEL Liossion is about 30 min. The bus trip from Athens to Trikala lasts for 5 hours and the trip from Trikala to Kalambaka for 30 min.

Alternatively, you can rent a car from Athens and drive yourself. The roads leading up to Meteora have been recently renovated allowing for a smooth experience.

The Monasteries of Meteora

Those six monasteries, in which monks and nuns still live today, are open to visitors. The monasteries are closed again and again, but all on different days, so that some of them can certainly be visited during a visit.

If you are short on time and can’t (or don’t want to pay to) visit all the monasteries, here are my favorites in order.

  1. Varlaam
  2. Holy Trinity
  3. Great Meteoron
  4. Rousanou
  5. St Stephen’s
  6. Agios Nickolas

Of course these are just my opinions and you might feel differently. If you have the time, just go ahead and visit all of them and decide for yourself!

One thing to note is that the bathroom situation in the monasteries are old school drop toilets. Some are nicer than others but the only monastery with a modern toilet is the Varlaam monastery. If you are scared of drop toilets like many Westerners are, then plan accordingly!

Great Meteoron

Great Meteoron Meteora Greece

With an area of ​​60,000 square meters, Metamórphosis is now the largest monastery on the Meteora cliffs . The monastery, which was built in 1334, lives up to its name “Floating”, because until 1923 it could only be reached via rope ladders or a net that could be pulled up.

Great Meteoron Meteora Greece
Great Meteoron Meteora Greece
Great Meteoron Meteora Greece

A stone staircase with 143 steps now leads into the interior of the monastery to make it easier to visit the founding monastery. The hermit cave of the monastery founder Athanasius can still be seen at the monastery entrance and in the monastery church you can admire ornate frescoes from 1552.

Agia Triáda – Holy Trinity Monastery

Meteora Holy Trinity

The spectacular Holy Trinity Monastery was built in the middle of the 15th century and, like the Megálo Metéoro, could only be reached via winches and rope ladders. Here, too, a staircase was built in 1925, which requires quite a bit of stamina.

In addition to the centuries-old frescoes , the main church of Agía Triáda is impressed by a silver- wrapped gospel from 1539. The real reason for the worldwide fame of the monastery, however, is its role in the James Bond film “On a Deadly Mission” as the fortress of the villain .


Agios Stéphanos – St Stephen’s Nunery

St Stephen's nunery meteora
St Stephen's nunery meteora

The first hermit allegedly lived on the spectacular cliff as early as 1192 and the monastery was founded around 1400. His nickname “The Royal” recalls the visit of Andronikos III, King of Byzantium, who was so enthusiastic about the hospitality of the monks that he made generous donations to them.

St Stephen's nunery meteora

Agios Stéphanos has been a women’s monastery since 1961, can be reached by car with almost no sidewalk and is primarily worth seeing because of its mother-of-pearl decorated church lecterns.


Meteora Greece

A monastery was built here in 1518 after a hermit had lived on the rock for many years. At that time, the place was not accessible to women. Today it is the second largest of the Meteora monasteries and the only monastery church with two domes. Remnants of the elevator, which consisted of rope and net, can still be seen.

Varlaam MOnastery Meteora Greece
Varlaam MOnastery Meteora Greece

Varlaam is probably my favorite monastery. It is the most beautiful in my opinion as the monastery grounds are superly maintained. To me, it’s the “poshest” monastery in Meteora with the most upscale decorations. You can definitely tell this monastery is well funded by the Orthodox church.

Agios Nikólaos Anapavás

The monastery merges directly into the rock and is one of the most impressive buildings on the Meteora cliffs. It can be reached via the nearby village of Kastraki. The complex is, so to speak, the crypt of the Meteora monasteries , because the skulls of former monks are kept in the Church of John the Baptist. The frescoes and paintings are also worth seeing.


Varlaam MOnastery Meteora Greece

It is not known exactly when the Rousánou Monastery was founded. Its peculiarities are also in the artistic wall paintings. The monastery was renovated in the 1950s and is now exclusively reserved for nuns. Rousánou offers a spectacular photo opportunity from a rock in the valley.

Rouseanou MOnastery in Meteora

Most of the remaining monasteries have fallen into ruins. Also worth mentioning are Filakaé Monakón , according to tradition, a rock cave into which monks who did not obey the monastery rules were sent, and Moní Ypsilotéra , also called Kaligráfon because of the manuscripts he wrote there. The ascent to the uninhabited monastery ruins is very difficult and in some places dangerous. Entering the ruins is prohibited due to the risk of collapse.

Two Weeks in Greece Itinerary – Day 6-9: Mykonos Island

From Meteora, you’ll have to drive back to Athens and fly from the airport there. I flew to Mykonos where I spent the next three nights. Mykonos is probably the second most visited island after Santorini and is famous for its beautiful Chora (the main town) and its beach clubs. With two weeks in Greece, this is a great island option to start your Cyclades adventures.

Mykonos Chora

Mykonos felt like the gathering place of the European Jersey Shore crowd mixed with all the semi-pro influencers you can find. Most times it felt like people were going that extra step to look better than they normally would. It’s like the Miami of Greece in a sense. Everything is also priced accordingly and you can expect to spend 2-3x more for almost anything in Mykonos versus the other islands in the Cyclades.

Little Venice Mykonos
Hard to compete with views like this in Mykonos
mykonos cavo tagoo pool bar susnet
€18 not enough for you? How about €22 at this epic bar in Mykonos
Agrari beach Mykonos

Nevertheless, it’s easy to avoid this by simply staying away from the fancy beach clubs and that whole vibe. The Chora is absolutely beautiful to walk around during the day when people are nursing their hangovers from the night before.

Church in mykonos
A famous church in Mykonos

It’s everything you’re looking for in that typical Cycladic village with its perfectly manicured cobblestone streets, white houses, and blue doors. I also really enjoyed the sunset from the Armenistis lighthouse as well as from the 180 degree sunset bar (even if the cocktails are €18 as of 2020).

Two Weeks in Greece – Amorgos Island: Days 9-12

From Mykonos, the next stop is a much less busy island and one of my personal favorites, Amorgos. Amorgos is perhaps the most dramatic and naturally stunning island in the Cyclades. It has huge mountains that overlook the Mediterranean, one of the most picturesque Choras, and a monastery built into the face of the rocky hills.

From Mykonos, there are daily ferries with Seajets and Blue Star to this island. When you book your accommodation, just be mindful of which ferry port you are arriving in as there are two ferry terminals on Amorgos.

Visit the Chora of Amorgos

Amorgos chora cycladic architecture

The Chora of Amorgos was the medieval capital of the island. In olden times, the inhabitants preferred to move their capitals from the seaside to high up in the mountains to avoid pirate attacks that were all the rage. You can find the same trends happening in islands like Sifnos, Milos, Folegandros and more.

Amorgos chora cycladic architecture
Amorgos chora cycladic architecture

The Amorgos Chora is without a doubt one of the, if not the most beautiful old towns in all of the Cyclades. It is the most rustic and authentic looking of any island I saw as you could see so many buildings that still had its original stones in tact.

amorgos chora

The beauty of the Chora is absolutely enchanting and walking through the old town was like walking through some sort of Cycladic fairy tale. There is one main street where all the restaurants, cocktail bars, and cafes are so simply walk down this street in the mid morning for an empty tour of the town.

Amorgos chora cycladic architecture

I particularly liked the area by Apospero cafe which had the most perfect tables set out on the most perfect white cobblestone streets with the most vibrant Bougainvillea trees. If you want the cutest towns in the Aegean, look no further than Amorgos.

Amorgos chora cycladic architecture

During the day times, it’s very quiet and devoid of people for most of the day. In the summer nights, the town fills up with people enjoying some of the top notch restaurants operating in the Chora. I visited during Coronavirus times and while the typical nightlife was a big no no, it was still very lively with mainly Greek tourists.

amorgos chora

There are few side streets as well that you’ll want to explore with more cafes, rustic whitewashed houses, doors painted in a variety of colors like blue, green, and red, and so much more. I thought I saw the most beautiful villages in the Cyclades, but was blown away by the Chora in Amorgos.

Amorgos chora cycladic architecture
Amorgos chora cycladic architecture
Amorgos chora cycladic architecture

Make sure to also walk up to the Venetian castle sitting on its rocky peak. You’ll find absolutely beautiful views of the Chora, sea, and the surrounding mountain scenery.

Amorgos chora cycladic architecture

And of course, make sure to take many many photos of yourself doing your finest Instagram vanity pose. I mean, I’m a guy without long blonde hair and a flowing white dress and even I could get myself into the swing of it!

amorgos chora cyclades greece
Amorgos Chora

Enjoy the stunning landscape of the island

I’ve visited countless islands in the Cyclades and have enjoyed all of them immensely. Each island has something to offer and something that stands out above others.

Panagia Hozoviotissa Monastery amorgos greece

Amorgos is a very special island in that the scenery is absolutely just breathtaking. While most of the other islands are mountainous to a degree, Amorgos is much more mountainous than others. The whole island being long and thin, you can see the mountains from every part of the island especially as it dramatically descends steeply into the ocean.

Panagia Hozoviotissa Monastery amorgos greece

It has some of the tallest peaks in the Cyclades behind Naxos and Paros. The difference is Naxos peak was in the interior of the island whereas Amorgos’ peaks can be seen from the ocean. The contrast is absolutely stunning and reminds me of driving through the Western cape on my way to Cape Point.

Amorgos landscape

There are so many heart-stopping viewpoints on this island that it’s best just to pull over on the ATV/scooter/car at times and just soak in the views.

Panagia Hozoviotissa Monastery

This is by and far the most amazing thing to see on Amorgos. The Monastery of Panagia Hozoviotissa in Amorgos should be much more famous than it is. In fact, I barely even heard people really talking about it while I was in Amorgos.

Panagia Hozoviotissa Monastery
The monastery from afar

Nevertheless, this 1000 year old Monastery is built into the mountain wall hundreds of meters above the sea, facing the sea. The all white facade is visible from the sea. This architectural marvel immediately brought me back to my time visiting Petra in Jordan with its mind boggling buildings carved into the face of the mountains.

The monastery is close to the Chora and is an absolute must visit. Don’t skip this one!

History of the monastery

Panagia Hozoviotissa Monastery amorgos greece

The monastery was built over a thousand years ago when monks escaped from persecution in Palestine and found refuge with the people of Amorgos island. They were allowed to construct this Christian monument which started sometime in the9th century.

Panagia Hozoviotissa Monastery amorgos greece

The monastery began to be built near the ocean where the icon had been found. Yet each day the builders came to work, whatever they had done the day prior was mysteriously knocked down by mother nature. This happened for a few days. Finally, the master builder lost his tool bag. It was found hanging off a nail on the cliff above. They all believed this was a miracle and a sign from Panagia to build the monastery up higher.

Funding ran dry for the construction numerous times and was left untouched numerous times. It wasn’t until 1088 AD when Emperor Alexios Komninos of the Byzantine Empire was informed that there was a monastery unfinished in Amorgos that he sent the necessary funds and finally completed it.

All in all, it took 250 years to finish building this structure! Really crazy to think that it took the entire history of the United States to finish the construction of this church.

Walking up to the Monastery

Panagia Hozoviotissa Monastery

From the entrance of the Monastery, it’s possible to walk up to the church and visit. There are a few hundred cobblestone steps to climb all while enjoying breathtaking views of the sea. It’s not a difficult hike and takes roughly 15 minutes to reach the top.

Panagia Hozoviotissa Monastery amorgos greece

The picture opportunities here are endless so make sure to snap some photos of this magnificent white structure. Once at the entrance, it’s possible to enter the monastery for a quick tour of the inside. Men have to wear pants and a shirt but they had random offerings available. Women also can’t wear pants or shorts but they have shawls available.

Once inside, I climbed to the top for a short tour given by one of the workers which was very interesting before going into a room to sample the local Raki made by the monks that still live there.

All in all, a very great experience!

Two Weeks in Greece – Day 12 to 15: Santorini

Santorini is the most famous and most visited island in all of Greece, and maybe even the world. This island is the ultimate in stunning views and photo opportunities. For the ladies, make sure to pack your favorite dresses and a sufficiently large hat which is key.

santorini blue domes greece
Santorini oia

Even if you’ve never heard of Santorini, there’s a high chance you’ve seen a photo of its iconic blue domes floating around somewhere. Mykonos has become the defacto upscale party island of Greece whereas Santorini has become the mecca for romantic couples trips, honeymoons, and influencer photo sprees.

Santorini is unlike the other islands in that it was formed by a volcanic eruption thousands of years ago. The entire island nowadays is built on the remnants of lava hardening in the sea. The island is very beautiful in that all the houses were built on the clifftops that descend straight into the sea allowing for dramatic effects.

The main towns of Santorini are Fira and Oia with the latter being the famous town that everyone takes photographs from. I would recommend one of the beautiful resorts in Oia or if you want exclusive privacy away from all the madness, stay somewhere in between Fira and Oia.

Santo Winery

Santo Winery

No visit to Santorini is complete without visiting the world famous Santo Winery. Santorini is widely regarded as the best wine growing island in all of Greece thanks to its rich volcanic soil (remember, Santorini is the remnants of a large volcano explosion thousands of years ago). Santo Winery is the largest producer on the island dating back to the 1940s.

Santo Wines has a large compound nearby to Fira town and it has perhaps the most stunning scenery that any winery in the world could hope to have. It’s literally in the middle of the Santorini crescent and offers completely unobstructed views of the sea.

Santo winery
Indoor seating
SAnto winery santorini
Outdoor seating
santo winery
More outdoor seating
SAnto winery santorini

The estate is set up with a modern interior perfect for wine tasting as well as numerous large outdoor patios for you to enjoy the breathtaking view. Santo Wines is actually popular for weddings and who could blame them?

We did a wine tasting here which included 12 of their wines (6 red and 6 white) for roughly €40. I actually thought this was crazy expensive considering I had been getting wine at restaurants for €4 for a half liter. Nevertheless, the wine here is of top notch quality but in reality you’re mostly paying for the view. The view is absolutely out of this world and is a must visit for this reason alone.

santo winery drinking wine
Drinking wine and enjoying the views
santo winery
Santo winery

The sun sets directly in front of the estate so it’s a hugely popular place for sundowners. A reservation is an absolute must if you want to come here for the sunset. Even during coronavirus times, this winery was packed full. If you come in the summer months in normal times, I’d make a reservation at least a week beforehand. Otherwise, you can still come here during the daytime without much issue. The sun is super hot so most people wait until sunset to come here in big numbers.

Do the Fira to Oia hike

If you want to mix up the Instagramming and upscale dining with some physical exercise (light of course), look no further than the hike from Fira to Oia.

I’m not sure I would really call this a proper hike as more of a long walk. It’s not very challenging as the terrain is novice and almost all of it is done on paved road. Nevertheless, if you want to get a good feel of what Santorini has to offer in terms of views and landscape, the hike from Fira to Oia is it. Fira is located in the center of the island while Oia is located at the northwest tip. Doing this hike essentially means you’ve walked half of the island. Not only will you be able to see the breathtaking views Santorini is famous for, but you’ll also walk through some of the lesser known towns in Santorini (which are also very worthwhile).

The hike can be done at any time of the day as there is no entrance fee you need to pay. You simply start in Fira, Santorini’s capital, and walk along the edge of the town until you find the start of the footpath that goes towards Oia. You can see Oia from Fira so really if you’re just walking along the sea towards Oia, you’re going in the right direction. If all else fails, just ask someone!

I recommend starting from Fira because the hike towards Oia is slightly less of an incline than the other way around. Of course, you can hike from Oia to Fira as well but just be prepared for more uphill. The next two towns are Firostefani and Imerovigli which are almost like suburbs of Fira and are on this footpath (you can’t miss it). Both are much lower key than Fira and because they are not as easily accessible for the swarms of cruise ship tourists.

To return to your starting point, simply take the frequent bus that goes between the two towns. This bus leaves every half hour so you will never have to wait that long. Alternatively, if you’re staying in Oia, take the bus to Fira first, and then walk back home. I’d recommend doing this hike in the morning hours as the sun can be very unforgiving after 11am.

The walk is approximately 10kms (6 miles) long and will take you through a variety of landscapes along the way. Make sure you set aside a decent amount of time to complete so you are not in a rush. Generally, it should take between 3-5 hours depending on fitness level, stops and the temperature.

The path changes terrain from everything such as loose scoria, concrete, sand and rocks. Good walking shoes with plenty of support is a must.

Day by Day Two week Greece Itinerary breakdown

Here is a breakdown of the day by day itinerary for spending two weeks in Greece.

Day 1: Land in Athens and explore the city
Day 2: Full day in Athens
Day 3: Athens to Meteora
Day 4: Full day Meteora
Day 5: Meteora back to Athens, Flight to Mykonos
Day 6: Full day Mykonos
Day 7: Full day Mykonos
Day 8: Mykonos to Amorgos
Day 9: Full day Amorgos
Day 10: Full day Amorgos
Day 11: Amorgos to Santorini
Day 12: Full day Santorini
Day 13: Full day Santorini
Day 14: Fly home

What If I don’t want to visit Mykonos or Santorini?

If visiting Mykonos and Santorini are not at the top of your list, what other islands should you consider? I know Mykonos and Santorini get all the recognition and the FOMO from first time Greece visitors but I can absolutely assure you that there are much more beautiful islands in the Cyclades to visit at a fraction of the cost.

Folegandros sunset
Sunset from Folegandros

For the purpose of a two weeks Greece itinerary, I will recommend you to choose from the following islands:

These are some of my favorite islands in the Cyclades and they are easily accessible from Athens by flight or ferry (depending on the island).

A popular option to to replace Mykonos and Santorini would be to combine islands like Naxos and Paros. Milos and Folegandros is another great option. Finally, Naxos and Amorgos might be my favorites. Amorgos is probably my favorite island in the Cyclades and definitely the most breathtaking.

Panagia Hozoviotissa Monastery amorgos greece
The views on Amorgos

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