The Perfect Cyclades Greek Island Hopping Itinerary

Johnny

I spent two months traveling around Greece during the times of Coronavirus. It was absolutely unreal to visit all these islands in the summer months without the typical summer crowds.

I had only been to the island of Crete before this trip which I absolutely loved so I knew coming back would the right decision. The Greek islands often times refer to the Cyclades islands which are world famous for their impossibly picturesque white houses, blue painted door and window frames, cobblestone streets, and mesmerizing beaches.Church in mykonos

Prior to visiting, I had seen countless photos of Cycladic islands throughout my travel career and now having been to a dozen islands, it more than lives up to the reputation. I had just over four weeks to travel the Cyclades and this itinerary will focus on what I did and how to plan your own trip out. Of course, not everyone will have four weeks like I did to travel but read through all the places I liked and plan your own trip accordingly with what you deem the most exciting!Mykonos Chora

 

Where I went in The Cyclades, Greece


So I had about 4 weeks to travel around the Cyclades. Prior to this, I was traveling through the Ionian islands of Zakynthos and Kefalonia (which has the most amazing beaches, more superior to the Cyclades for sure), as well as the capital of Athens (which is a must)!

Perallia Patani Beach

If you’re looking for beaches like this, you’ll need to go to the Ionian islands

shipwreck beach Zakynthos view

If you’re looking for this view, you’ll also need to go to the Ionian islands.

This is of course more than what most people will have but I thought it really helped me see all the places I wanted to without rushing through it. I also traveled during the times of Coronavirus and was able to work remotely which helped me take the additional time necessary.

octopus drying greece

Octopus Drying in front of Medousa

Don’t worry, I will help craft itineraries if you have one week or two weeks which is of course the more common route!

 

Traveling during Coronavirus

I visited Greece in the summer of 2020. Summers are the peak season travel and normally I would steer clear from all the Greek islands during these months because it gets crazy. However, in 2020, during the Coronavirus pandemic, it was probably the best decision I could have made to visit Greece.

The crowds were a fraction of what they normally see and I was able to see a Greek summer that probably hasn’t happened in decades. Places like Santorini at the end of August was still a bit of a zoo which only makes me shiver at the though of Santorini during a normal August, aka the last place on Earth I’d like to be.

Amorgos chora cycladic architecture

A lot of empty streets

In total, this itinerary is anyone that has about a week or so to dedicate to this itinerary. Of course this itinerary can be shortened or lengthened depending on your schedule. I visited the following areas on this itinerary

If these places ring a bell and sound like the places you want to visit, this is the perfect itinerary for you!

 

What do I need to know about traveling in the Cyclades?


The Cyclades archipelago is one of the most famous and beautiful parts of Greece. It’s very developed and is quite easy to travel through. Regular ferry connections are possible between the islands and there are nice paved roads in every place.

The food in Greece is among the best in the world so no matter where you go, you will be well fed with fresh Greek food and delicious Greek wines.

Greek salads

One thing is for certain, you will eat like a king all day every day.

Generally, most people come to Greece in the summer months which are its warmest and busiest. However, if you aren’t into big crowds, traveling during the shoulder months might suit you better.

There are a ton of different factors to know about the Cyclades that it can be its own post. And what do you know? I have done exactly that. Make sure to read my ultimate guide to traveling the Cyclades in conjunction with this itinerary to understand all the nuances of traveling here!

 

How to structure your island hopping trip?

Structuring your trip properly can mean saving an extra day or two just from catching the ferries correctly. The itinerary I will list out is indeed the islands I visited but not in the order that I visited. What I will write on this post is the optimal route for traveling the Cyclades. I did not do this optimal route opting to kind of go all over the place.

While I visited all these islands, I kind of went to one corner before coming back to another corner and so on. I could have saved a lot of time and money if I just followed the route correctly.

If possible, I’d recommend structuring your island hopping trip to visit the islands closest to each other and kind follow the logical path forward.

For example, if you’re flying in and out of Mykonos, you should try and do a circular route so to minimize the distance you need to travel by ferry. This would mean something like

Mykonos > Naxos > Paros > Sifnos > Milos > Folegandros > Ios > Santorini > Amorgos > Mykonos

Generally, I like to spend 3-4 nights in each island. Two nights is enough to see the highlights but I think even the smallest island deserves three nights to really relax and fully explore the island by scooter/ATV.

 

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!

 

Full Greek Islands Itinerary


This itinerary starts in Athens, Greece’s capital. There are many international flights that arrive into Mykonos and Santorini so technically you do not have to start in Athens for a Greek island hopping trip. However, it’s a travesty not to visit the capital in my opinion as it has so much to offer.

180 degree sunset bar mykonos

Everyday is an epic sunset like this.

From Athens, I took a flight to Mykonos to start my island hopping trip. The whole reason I did not take a ferry from Athens to Mykonos (which there are countless options), is because the flight was actually cheaper than the ferry and it takes less than 30 minutes. This is the only flight I took until I flew home from Santorini.

From Mykonos, I went to Naxos, the largest Cycladic island famous for its picturesque ancient villages. This is the logical next step from Mykonos because it is only 1 hour away.

From Naxos, I continued on to Paros island which has some of the cutest cycladic villages you will find. After Paros, I went to Sifnos which was absolutely beautiful for its mountainous terrain and adorable villages. Then came Milos which is known for its beaches and cuisine. Folegandros was next which is a much smaller island with some of the best views you can find. The sunsets here were unbelievable.kiki's taverna mykonos

From Folegandros, I continued to Ios which kind of the poor man’s Mykonos known for its parties and good vibes. However, in Coronavirus times, it wasn’t much of a party island but it was still home to a beautiful Chora and stunning beaches. After Ios, I went to Amorgos which had probably the most picture perfect old town, the most dramatic landscapes and by the most amazing church that was chiseled into the mountain.

Finally, I ended in Santorini which everyone and their mothers know about.

Here is a map of all the islands I went to. I know that if you’ve not been to this area before, looking at this map will confuse the hell out of you but just follow along with this map as well as the itinerary below.

 

Day 1-4: Athens


The itinerary starts in Athens, Greece’s modern day capital! Athens is an amazing city that is certainly underrated compared to the other European capitals. It’s home to so much history and wonderful monuments that you’ve probably learned about in school. The world famous Acropolis home to the Parthenon is here visible from all parts of the city.Athens acropolis parthenon sunset

The food and drinking scene in Athens is also top notch. There’s a palpable sense of energy here that you can feel as soon as you step out. I had some amazing cocktails and rooftop drinks here as well as eating some of the finest cuisine that Greece has to offer.Odeon theater show summer athens

I stayed in a beautiful Airbnb with unobstructed views of the Parthenon which I’d highly recommend. You don’t really need that much time in Athens if you’re just concerned with seeing the main sights. However, I adored the vibe and feel of the city and could have easily stayed a week here.Athens restaurant square

If you don’t plan on visiting Athens and have a direct route into the islands (like Mykonos or Santorini), then ignore this part of the itinerary and move to the next section.

Blue aegean negroni clumsies bar athens

The famous aegean negroni at Clumsies, one of the top rated bars in the world.

Read my detailed post about visiting Athens!

 

Day 4-7: Mykonos Island


From Athens, 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.Mykonos Chora

Because of COVID, the beach clubs were open but not at its full capacity. 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.

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

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. 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).Agrari beach Mykonos

Read my detailed post about visiting Athens!

 

Day 7-11: Naxos Island


From Mykonos, the logical next step is to go to Naxos Island. There are numerous ferries that run from Mykonos to Naxos every day and the journey is only one hour.Temple of Apollo Naxos

Naxos is the largest island in the Cyclades and perhaps the one with the richest history. In olden times, Naxos was the center of the Cyclades in terms of trade, culture, and civilization. Nowadays, it’s no longer the capital (that would be in Syros), but it still has palpable energy, history, and beautiful villages to boot.Temple of Apollo Naxos

The main town in Naxos is the Chora, which is also the port town. As soon as you dock into the island, you can see the beautiful main town with its white houses built around a small hill with a Venetian castle at the top. Nearby the Chora is the famous Temple of Apollo famous for its huge marble gate overlooking the city.

Chalki Village Naxos

Chalki village

Chalki Village Naxos

The Chora itself is very pretty although not as picture perfect as Mykonos.

My favorite part of Naxos was exploring the inner parts of the island. Not only is the landscape absolutely stunning but the villages are some of the most stunning I found in the Cyclades. These included Chalki, Filoti, Apeiranthos, and Koronos. A day trip to explore these villages is a must to not only get a feel for the history of the Cyclades but just taking some of the best photos you can get.Filoti Village Naxos

Naxos cycladic house

Look at that beautiful house!

Koronos Naxos town

Beautiful Koronos

Koronos Town Naxos

Naxos is also famous for its many beaches. You’ll find long sandy strips with calm sea all around the island. From Naxos, you can also take day trips to the Lesser Cyclades islands which I sadly did not have the time to visit! These include Iraklia, Koufonisi, Schoinousa, and Donousa. These very small islands are renowned for their incredible beaches and quaint villages. You will see plenty of day trip operators that operate an island hopping trip from Naxos to Koufonisia.

Read my detailed post about visiting Naxos!

 

Day 11-15: Paros and Antiparos


From Naxos, take the ferry to the nearby island of Paros. This is probably the second largest island in the Cyclades but has an entirely different feel to Naxos.Lefkes town paros greeceNaoussa Paros Greece

The port town of Paros is an okay town but I would highly recommend basing yourself out of the much more picturesque and charming town of Naoussa in the north. This is where all the action happens as all the hip restaurants, bars, and shops are here. Naoussa also has an absolutely beautiful town center filled with all the Cycladic features you’re craving.Lefkes town paros greece

From Naoussa, it’s easy to explore the other villages on the island that are equally as picturesque if not more so. Lefkes and Marpissa are definitely the ones I recommend the most.

Marpissa town paros greece

 

Antiparos day trip

If you’re in Paros for more than 3 days, I’d definitely recommend taking one of those days to explore Antiparos. Anti, which means opposite in Greek, is the smaller island southwest of Paros. Antiparos was mostly just a fishing village throughout its history until the last few decades where it has really picked up steam with visitors. Greeks and foreigners alike have discovered Antiparos and it’s kind of become the place to go.antiparos greece

The town is incredibly charming with all the bells and whistles you’re looking for in a Cycladic village. The island also has many nice beaches which are much less busy than Paros.

antiparos greece

 

Day 15-18: Sifnos


After Paros, take the ferry again to the nearby island of Sifnos. Sifnos is one of my favorite islands in the Cyclades. It’s much smaller than Naxos and Paros but has so much charm packed in. Sifnos has a very dramatic landscape with mountains that have white churches at the top.Artemonas Town Sifnos

The port town of Kamares is charming and a perfect place to base yourself for exploration. The Chora of Sifnos is named Apollonia and is located in the center of the island up in the mountains. In olden times, the people here built their main towns in the middle of the island so it was not visible from sea in order to avoid pirates. Apparently that was a big thing back in the days.

Kamares Town Sifnos

View of Kamares Town

Nowadays, Apollonia and the nearby town of Artemonas are where the action is. All the restaurants, bars, and shops are here and it is so charming. The streets are absolutely adorable here and the island sees much fewer tourists than its neighbors.Artemonas Town Sifnos

Kastro is the third town that is a must visit. It’s the oldest village on the island with a walled in city that just screams beautiful. I couldn’t get enough of it while walking through it and enjoying a nice drink from the castle.

Kastro Town Sifnos

Look at how beautiful this is!

 

Day 18-21: Milos Island


After a wonderful few days in Sifnos, the next island in Milos. Milos is famous for its delicious food and wonderful beaches. I must admit that I had some of my best meals in Milos and perhaps the most fantastic seafood at the Medousa restaurant in the fisherman village of Mandrakia.klima milos fishing town

Milos also has one of the most charming villages in the Cyclades. The capital, Plaka checks off all the boxes when it comes to white houses, beautiful churches, cobblestone streets, and perfectly painted doors. Down the road is the impossibly quaint fishing town of Klima which is a must see as well.Plaka town milos

Milos is also blessed with an array of beautiful beaches with stunning rocky backdrops that look more like the American southwest than it does a Mediterranean seaside.Fyriplaka Beach Milos

 

Day 21-24: Folegandros Island


From Milos, it would be a travesty to not visit Folegandros, directly east of it. Folegandros is without a doubt one of my favorite Cycladic islands (have I already said this?). It’s one of the smaller islands in the archipelago with really only one town, the Chora.Folegandros Chora

Not all Choras are created equally and Folegandros has one of the most charming ones yet. Its cobblestone streets and beautiful houses make it a photographers dream. Make sure to also visit the Kastro neighborhood within the Chora for medieval houses that have stood for hundreds of years. For sunset, make sure to hike up the windy footpath of the Church of Panagia. The views from this church are absolutely stunning as the sun sets over the sea and mountains.Kastro Neighborhood Folegandros Chora

Folegandros is an island that’s much less visited than its neighbors (although summer months can still get busy) and you can tell by how the island is not set up for mass tourism.folegandros chora

The topography of Folegandros is also stunning. It’s a very mountainous island with the main road and town built in the middle at its peak. Driving down the main road will afford you with spectacular views of the sea and surrounding islands.sunset folegandros chora

I spent three nights here relaxing and taking it slow. There really isn’t that much to do in Folegandros because of how small it is so you can focus on just enjoying the little things. I did scuba dive in Folegandros one day with Sea U. While the diving itself is okay, the visibility here was out of this world.Folegandros Chora

 

Day 24-27: Ios


From Folegandros, I took another ferry to the party island of Ios.Ios Chora

Yes, Ios is known as the party island among Greeks. It’s somewhat of a poor man’s Mykonos in that Ios isn’t as flashy or fancy as Mykonos which has grown to be the international hotspot for influencers. Ios has been a party island for Greek people for decades and it doesn’t try to hide the fact.Ios Chora

The Ios Chora is still very beautiful but not as perfectly manicured as Mykonos. Instead of high end clubs, there are bars serving shots for €1. Ios is certainly geared more towards a younger crowd.

Pathos Beach Club

One of the famous beach clubs in Ios

Since I visited during the summer of Coronavirus, bars were ordered to close down early and dancing was prohibited which means the famous nightlife Ios is known for simply did not happen. I actually really enjoyed the island for its non-party vibe which included some fantastic Greek restaurants, some of the best beaches in the Cyclades, and a beautiful Chora.

 

Day 27-30: Amorgos


Amorgos is the next island on the list. There are no direct ferries from Ios to Amorgos so I had to transfer ferries in Naxos (which was still pretty easy).Amorgos Chora

Amorgos is the furthest east island in the Cyclades and it might just be my favorite island in all of the Cyclades. The landscape in Amorgos is absolutely stunning with its high peaks and steep dropoffs into the sea. The island is long (40km) but thin (5km wide) and it’s not a heavily populated island. Most of the action happens in the Chora and the two town port towns of Aegiali and Katapola.Panagia Hozoviotissa Monastery amorgos greece

The Chora is built high in to the mountains in the middle of the island. It’s perhaps the most picturesque Chora of all the towns I saw in the Cyclades. The town is much older than say the Chora in Mykonos and while it’s been very well kept up, it maintains its rustic and historic feel.Amorgos chora cycladic architecture Amorgos chora cycladic architecture

Walking down the few streets in the Chora is absolute bliss. There are more photography opportunities here than anyone can handle. The perfectly painted white houses and the abundance of pink Bougainvillea trees means that all your Cycladic needs will be satisfied here.Amorgos Chora

In addition, among the seemingly thousands of white churches throughout the Cyclades, the monastery of Hozoviotissa reigns absolutely supreme. It’s a huge church that’s chiseled into the mountains of Amorgos high up above the sea. It totally reminds me of Petra and is by far the most stunning monument I saw in the Cyclades.

Amorgos Chora

But much better during the day time!

Agia Anna beach amorgos Greece

Read my detailed post about visiting Amorgos!

 

Day 30-34: Santorini


Last but certainly not least, what long term trip through the Cyclades is complete without a visit to the mother of them all in Santorini. Santorini is the most famous and most visited island in all of Greece, and maybe even the world.santorini blue domes greece

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 oia

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 stayed in an Airbnb with direct views onto the famous three blue domes and there was an endless line of people waiting to take photos.

Santorini is extremely overwhelming during the summer months with thousands of people per day descending into the small towns. I would highly advise visiting in July and August.

 

Day by Day breakdown of my Greek island itinerary


Here is a day by day breakdown of the Greek island itinerary. It’s pretty involved each day so absolutely feel free to spread it out over more days if you have the time!

Day 1: Land in Athens, explore the city
Day 2: Explore Athens, including Acropolis
Day 3: Explore Athens
Day 4: Flight to Mykonos
Day 5: Fully day in Mykonos
Day 6: Mykonos
Day 7: Ferry to Naxos
Day 8: Full day exploring Naxos
Day 9: Explore the villages in Naxos
Day 10: More of Naxos
Day 11: Ferry to Paros, stay in Naoussa
Day 12: Explore Paros and its villages
Day 13: Beach day in Paros
Day 14: Day trip to Antiparos
Day 15: Ferry to Sifnos
Day 16: Full day in Sifnos
Day 17: Full day Sifnos
Day 18: Ferry to Milos
Day 19: Full day Milos
Day 20: Full day in Milos
Day 21: Ferry to Folegandros
Day 22: Explore Folegandros island
Day 23: Beach day in Folegandros
Day 24: Ferry to Ios
Day 25: Full day in Ios
Day 26: Beachs in Ios
Day 27: Ferry to Amorgos, via Naxos
Day 28: Explore Amorgos
Day 29: Full day in Amorgos
Day 30: Ferry to Santorini
Day 31: Full day Santorini
Day 32: Hike from Fira to Oia
Day 33: More Santorini
Day 34: Fly home

 

One week Greek Island Travel Itinerary


If you have one week to travel the Greek islands, here are some options for you to consider. Let’s just assume this week is dedicated to the islands and Athens won’t be in the picture.

Of course with just a week, you won’t be able to visit that many islands especially if you want to spend three nights in each island. Nevertheless, I think if you want to explore as much as possible, it’s totally acceptable to do two nights in an island. Just be mindful of the ferries because if you are traveling long distances (like Mykonos to Milos), this could eat up most of a day.

cycladic house paros greece

Stay in a beautiful cycladic house like this

 

See the most popular islands

Talk to anyone who’s been to Greece and they’ll probably tell you they’ve been to Mykonos and Santorini. Of course, I think these islands are worth a visit and if you can’t live with FOMO, then check these places off the list.

I would structure this trip in such a way:

Day 1: Arrive in Mykonos
Day 2: Full day in Mykonos
Day 3: full day in Mykonos
Day 4: Ferry to Santorini (many ferries each day)
Day 5: Full day Santorini
Day 6: Full day Santorini
Day 7: Fly home from Santorini

If you want to explore more than just Mykonos and Santorini, do something like this:

Day 1: Arrive in Mykonos
Day 2: Full day in Mykonos
Day 3: Ferry to Paros
Day 4: Full day in Paros
Day 5: Ferry to Santorini
Day 6: Full day Santorini
Day 7: Fly home from Santorini

 

Visit the more quaint islands

If Mykonos and Santorini aren’t a necessity, then I would do something like this. Remember, you can fly into some of the islands from Athens or take a ferry.

Day 1: Arrive in Paros
Day 2: Full day in Paros
Day 3: Ferry to Naxos
Day 4: Full day in Naxos
Day 5: Ferry to Amorgos
Day 6: Full day in Amorgos
Day 7: Ferry back to Naxos for a flight back to Athens

Or if you want to visit Milos:

Day 1: Arrive in Santorini
Day 2: Full day in  Santorini
Day 3: Ferry to Milos
Day 4: Full day in Milos
Day 5: Ferry to Folegandros
Day 6: Full day Folegandros
Day 7: Ferry back to Santorini, flight home from Santorini

 

Ten days Greek Island Travel Itinerary


With ten days (so a Friday to the following Sunday type of trip), you can add another island to the mix or just not be rushed through so many islands at once.

 

Mykonos to Santorini (or vice versa)

Day 1: Arrive in Mykonos
Day 2: Mykonos
Day 3: Naxos
Day 4: Naxos
Day 5: Amorgos
Day 6: Amorgos
Day 7: Santorini
Day 8: Santorini
Day 9: Santorini
Day 10: Fly home

 

Two week Greek Island Travel Itinerary


I think with two weeks in the Greek islands, you will be able to really get a good feel for the life here and see some things. If you’re coming on a Greek honeymoon for example, then this is the perfect time to plan a whole trip through Greece which includes Athens and then a visit to the islands. Or if you are sea-starved, just focus your entire time in the islands which is also easy to accomplish.

 

Mykonos to Santorini (or vice versa)

This itinerary will check off the two “popular” islands as well as giving you time to visit the more quaint islands in the Cyclades.

Day 1: Arrive in Mykonos
Day 2: Mykonos
Day 3: Paros
Day 4: Paros
Day 5: Paros
Day 6: Naxos
Day 7: Naxos
Day 8: Naxos
Day 9: Amorgos
Day 10: Amorgos
Day 11: Santorini
Day 12: Santorini
Day 13: Santorini
Day 14: Home

 

Western Cyclades

This itinerary will visit the western side of the Cyclades. It can either start from Mykonos or Santorini depending on your preference.

Day 1: Arrive in Mykonos
Day 2: Mykonos
Day 3: Paros
Day 4: Paros
Day 5: Paros
Day 6: Sifnos
Day 7: Sifnos
Day 8: Sifnos
Day 9: Milos
Day 10: Milos
Day 11: Folegandros
Day 12: Folegandros
Day 13: Folegandros
Day 14: Ferry to Santorini to fly home

Continue Reading:

The Perfect Cyclades Greek Island Hopping Itinerary

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