Island Hopping on the Cyclades - a Two Week trip to Greece

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Island Hopping on the Cyclades - a Two Week trip to Greece

The Cyclades are a group of Greek islands in the southern Aegean Sea. They are mostly known for their towns with small streets and typical white Cycladic houses. The most famous and popular Cyclades islands are Santorini and Mykonos. We want to show you a three-week trip with island hopping to the most beautiful Cycladic islands. With our guide you will find the best photo opportunities, from the most beautiful white and red churches, to the most picturesque cobbled streets and houses planted with bouganvilia, to the most impressive viewpoints.


There are three different ways to get to the Cyclades:

  1. flight (via Athens) to one of the Cyclades islands.

  2. flight to Athens and ferry to the islands

  3. ferry from Italy (Ancona, Brindisi,Patrasso, …) to Greece (Igoumenitsa, Patras, Piraeus, …) and another ferry to the islands (for the faster way with your own car)

  4. by car overland (for those who plan a longer road trip ;))

Of course, the most comfortable and fastest option is a flight directly to one of the Cyclades islands. The journey with your own car is probably only interesting for those who plan a Greece road trip.


Between the islands

To get from one island to the next there is the possibility to fly (during our visit there were only flights via Athens between the islands no direct flights) or the easiest and cheapest option by boat. Between the Cycladic islands there is a good network of ferries, passenger floor and high-speed boats that bring you for cheap money usually at least once a day to the island of your choice. When traveling by boat, however, you will have to be patient from time to time, as due to the “Meltemi” (wind in the Cyclades) boats can break down from time to time. More susceptible to breakdowns are the high-speed boats and small passenger ferries, as they can only sail up to wind force 7-8 Beaufort. Large ferries can usually still sail with winds up to Beaufort 9. In strong winds, the journey can be postponed by one or two days. Our landlady just said “Islands, you know, slow life”.

On the islands

All Cyclades islands are very small but hilly. On most of the islands, the main sights are in the big cities, mostly where the ferries dock. In the cities themselves, it is very easy to get everywhere on foot. To explore more of the island it is worth renting a car (or quad or scooter) for a day. Free parking is available in most places. If you like it sporty you can also rent a bike. Since the distances on the island are very small, you can easily get everywhere with a bike, but you should be prepared (depending on the island) for somewhat mountainous roads and there are usually no separate bike paths.

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View at sunrise to the Sotero church on Syros


The Cyclades are a destination for the whole year. Especially for those who want to escape the gray autumn or winter in Germany, the Cyclades are perfect. Here, even in autumn and winter, many flowers are still in bloom, including the famous bouganvillias, and you feel like you are in a prolonged summer.

  • Spring (March - May): In spring there can be more rainfall. At this time of year, the islands appear a bit greener than in autumn. There are also fewer tourists before summer.

  • Summer (June - August): Summer is the main season on the islands. The weather is actually always sunny and hot and rain is a specialty. For swimming on the beaches, summer is the best time. At this time, the party islands of Mykonos and Santorini are also very crowded.

  • Autumn (September - November): In autumn it becomes increasingly colder but it is usually still pleasantly warm with 20°C in November. From November on the rainy days increase, but during our visit in November it rained only x times in 4 weeks and 90% of the days were sunny. In the low season the biggest visitor storms of the summer are over and it slowly becomes quieter (especially on the well visited islands Mykonos and Syros).

  • Winter (December - February): In winter it can cool down a bit more and there are more rainy days but you can still count on mostly nice weather. In this time there are less tourists which makes a stay on Santorini or Mykonos more pleasant for photography. However, from the middle/end of November many tavernas and restaurants close, as well as most stores that cater to tourists.

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Our island hopping trip

We chose to visit the 5 islands of Mykonos, Syros, Paros, Naxos and Santorini. A trip across the islands is easily doable in two to three weeks. We show you our trip with details about photo spots, accommodations and travel tips. Our trip starts in Mykonos and goes via Syros, Paros and Naxos to Santorini from where we flew back.

Day 1 - 3 Mykonos

🛌 Sunday Summer House (Mykonos Town) ->

📍 5 windmills by the sea, Little Venice view, Panagia Paraportiani church and church in the big square behind, windmill by Portobello Boutique Hotel, Agiou Sotera church, Agios Nikolaos church, Happiness Mykonos, Armenistis lighthouse, Panagia Tourliani monastery in Ano Mera, church by ruins with cactus (near Ano Mera).

In Mykonos, it is best to take a cab from the airport (which costs a flat rate of 15€) to the town (about 3km walk). There is also a public bus from the airport to the town (in winter, however, only once an hour). If you arrive by ferry, you usually arrive at the New Port and it is best to take a cab as well (also 15€ flat rate, also about 3km walk). Alternatively, you can take a boat shuttle (about 3€) from the New Port to the Old Port during the summer months (March to October). Our apartment the Sunday Summer House was located at the upper end of the city (a bit up the hill), from where you can enjoy a great view over the bay and the city from most of the roof terraces. In 10min you are at the Old Port and the windmills.

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Tiny churches with their red rooftops in the white village of Mykonos

The old town “Chora” of Mykonos town is not very large but crisscrossed by many small nice cobbled streets that lead past countless white Cycladic houses and colorful doors with bouganvillias. Most of the time we just let ourselves be carried through the streets and just walked along where we saw the next photo motif. But of course there are some classic photo spots in Mykonos like the 5 windmills on the water (sunrise and sunset!) and the view from there to the houses of Little Venice built on the water (very nice light at sunset). Less known are the two windmills further up in the city from where you have a great view over the white sea of houses and also on the 5 windmills on the water (nice view at sunset). A famous photo spot is also the white church Pangia Paraportiani and the Agios Nikolaos located at the old harbor. Throughout the old town you will find countless other churches with red roofs that make super photo motifs such as the church Agiou Sotera.

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If you rent a car you can make a trip to Ano Mera, where the beautiful monastery Panagia Tourliani is located. Also, a bit up the hill at Ano Mera you will find the ruins of an old Venetian fort (not much to see anymore) and next to it a nice little church framed by cacti that makes a great photo. The Armenistis lighthouse is another place for sunsets but is not so easy to photograph because of various power poles.

From Mykonos you can reach Ermoupoli on Syros with the fast boats of Sea Jets (ca. 23€, 45 min) or the ferries of Blue Star Ferries (ca. 11€ 1h 15min).

  • 1 day: Delos
  • 1 day: Tinos
Windmills of Mykonos at sunset
Windmills of Mykonos at sunset

Day 3 - 5 Syros

🛌 Fimaira Apartments (Ano Syros) ->

🍽 I Apáno Chóra (music on weekends).

📍Ermoupoli: Asteria Beach Viewpoint, Church of Agios Nikolaos, Miaouli Square and City Hall, View of the city from the port at Nesaki parking lot, Church of Metamorfosi, Church of Anastaseos tou Soteros, Ano Syros: Ekklesia Agios Georgios, windmill at Ano Terma, small church Sa Michales, view of Ermoupoli above the church Naos Agiou Nikolau tou phtochou, island tour: San Michalis, view from the road to Kini (near Alithini) over Ermoupoli, Kini Beach, red rocks at Kokkina Beach

Ermoupoli on Syros is the capital of the Cyclades. The city is unlike Mykonos or Parikia and Naoussa on Paros not completely in white but is kept in pastel colors. The houses are much higher and you can tell that almost 20,000 people live here. Just like the city, the churches here are more colorful and larger. The most famous photo motif in Ermoupoli is the church Agios Nikolaus seen from Asteria Beach, from where it stands on rocks above the sea. It is best to come to Asteria Beach in the morning or at sunrise for the best light. Two other beautiful churches in the city are the church of Metamorfosi and the church of Anasteos tou Soteros, perched on the right hill above the city. The town hall, located in Miauoli Square, and the whole town have the best light from morning to noon. For a photo of the town hall and Soteros church, it is best to walk along Elitheriou Benizelou street towards the port.

View church Anastaseos Ermoupoli Syros
View of the Sotero church in Ermoupoli on Syros
Asteria beach church Agios Nikolaus
View from Asteria beach on the church Agios Nikolaus

The old town of Ano Syros, perched on the left hill above the city, offers a great view over Ermoupoli and the Sotero church, especially at sunset. In the small alleys you can find more photo opportunities as well as a windmill.

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The old town of Ano Syros on the hill behind Ermoupoli

Leads more great views is worth a short drive across the island. In the north of the island, the road leads into sparsely populated area to San Michales. There are some small churches and deserted bays and beaches that can be reached with a little walking. Towards the west the road from Ermoupoli leads steeply up the mountain. At Alithini you have another great view from above over the whole town. On the way down towards Kini Beach you also get a great view over the coast and you can go swimming at the beach in Kini. For a long round trip you can drive from Kini down the coast via Finikas to Megas Gialos and Vari. BEi Finikas there is another photogenic beach, Kokkina Beach, which lies below red rocks.

From Syros, Blue Star Ferries sails passenger boats (approx. 11€, 1h30min) to Parikia on Paros.

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View over the bay and town of Kini Beach

Day 5 - 6 Paros

🛌 Seaside Villa Germanikia (Parikia) -> Airbnb

📍 Parikia: Church of Panagia Ekatontapyliani, Church of Agios Konstantinos, Frankish Castle, Church of Agios Nikolaos Nauossa: old harbor, jetty to the Venetian fortress, jetty of the Naoussa Marina, Church of Kimisis Theotokou, Paralia Kolimbithres, Monastery of St. John’s of Deti, lighthouse of Korakas Marpissa: church Agía Ánna, church Metamórfosi Sotíros, monastery St. Antionios Lefkes: corner house with bouganvillia, church Agia Triada

Our next island is Paros. Unlike the previous islands, there are several interesting towns here that have a lot to offer: Parikia, Naoussa, Marpissa and Lefkes. In all of them it is worth to walk through the small streets with white Cycladic houses to discover the many nice houses with bouganvillias and small churches.

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little church in the streets of Parikia on Paros

In Parikia the big ferries dock. We therefore decided to look for an accommodation in Parikia. The place also has some nice alleys and churches to offer and a large selection of tavernas and restaurants. Parikia is also home to the famous church Panagia Ekatontapyliani, a historic church complex that is definitely worth visiting. Other beautiful churches include Agios Konstantinos next to the Frank Castle and overlooking the bay and Agios Nikolaos. We found the small white streets and houses in Parikia even more beautiful than on Mykonos.

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a white house in Parikia topped with beautiful bouganvilliaes

More known than Parikia is on Paros the place Naoussa. The small old harbor with fishing boats framed by white Cycladic houses and the bridge to the Venetian fortress are probably the most famous photo spots in Naoussa. The best light here is in the evening. Also from the pier of the Naoussa Marina** you have a great view of the city with the church Kimisis Theotokou** which is prominently enthroned on the hill. It is also worthwhile to climb through the small streets up to the church and discover nice corners in the white tangle of streets. In the bay near Naoussa is also probably the most beautiful beach of Parikia (at least as far as the photographic aspect is concerned): Paralia Kolimbithres. The interesting rock formations offer a great opportunity for creative photography. A bit further on the headland you can visit the monastery of St. John’s of Deti or take a short hike to the lighthouse of Korakas.

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Harbour in Naoussa with view to the church on the hill
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Cat on the walkway to the old fortress in Naoussa

Marpissa is a small town on the east side of the island. The town is an insider’s tip on Paros. Here we liked strolling through the white streets the most. At every corner there were beautiful churches and photogenic house entrances. Typical for Marpissa are the many round arches that connect the churches with neighboring houses and make a super photo location. Among other things, we found the white Church Agía Ánna with the entrance with bell tower directly next to the large main church of the village Metamórfosi Sotíros most beautiful. Next to Marpissa on a steep hill there is also the Monastery of St. Antionios with a beautiful bell tower and view.

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a little church in the streets of Marpissa on Paros

The highest village on the island is Lefkes. Here you can also find the top Instagram spot on Paros, the entrance of a corner house with a beautiful bouganvillia. The most prominent building in town is the Church of Agia Triada. You can get the most beautiful view over the town from the street by the Flora restaurant or from the Paros Traditional Windmill hotel. As everywhere, it is worthwhile to stroll through the streets and find your own favorite corners.

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corner house with beautiful bouganvillea in Lefkes

From Paros you can easily get to Naxos in 45min by ferry. Due to the restrictions of Corona we did not make it to Naxos and Santorini, so in the following we only present what we have researched and hope that we can complete the article soon with our personal travel information!

  • 1 day: Antiparos

Day 6 - 8 Naxos

📍 Portara, Chora, Temple of Demeter, Chalkio lemon liqueur production, Damalas, Aperathos marble city, graffiti on ruins at the cedar forest of Alyko.

Naxos is one of the largest and therefore known as the greenest Cyclades island. The most famous photo motif here is the Portara overlooking the sea. Besides the old town of Chora, there is a lot to discover on the island, which is why it is worthwhile to get a rental car here. Next to the Portara you can visit the archaeological site of the Demeter Temple, where some things are still preserved. On Naxos you can also learn about the production of lemon liqueur in Chalkio, where guided tours are offered. Besides the Chora you can explore the towns of Damalas and Aperathos.

From Naxos you can take the ferry to Santorini in about 3h.

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cycladean cats in Ano Mera on Mykonos island

Day 8 - 13 Santorini

📍Oia(Londsa Castle, Ammoudia, Panagia Platsani, Blue Dome Church, Nikolaou Nomikou Church), Cape Coloumbo, Pyrgos (Castle, Saint Mary Church), Skaros Rocks, Megalchori(Street with Bell Tower, Heart of Santorini, Parthenios House), Imerovigli, Fira Santorini Old Harbour, Caldera Hike Oia to Fira, Kokkinopetra Beach, Akrotiri Lighthouse, Paralia Vilchada, Emporio(Windmills, Venetian Castle), Old Thera

Although Santorini is a small island, it has many great photo spots to offer. This is one of the reasons why it is so crowded in the summer. If you like it a bit quieter, it is better to come in the off-season. Besides the famous photo spots in Oia with blue church domes and white houses, Santorini also has many other great photo motifs ready. The steep rocky coast with beaches like at Kokinopetra, the Skaros Rocks, the Heart of Santorini or the beach Paralia Vilchada is also a great photo motif. In the towns like Pyrgos and Megalchori or Emporio you can find more photogenic churches, bell towers and houses. Therefore, it is definitely worth to explore the whole island.

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sunset on the shoreline of Paros near Parikia


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