Island-hopping around the Cyclades - Traveling Psychiatrist

The Cyclades. A group of 24 inhabited islands (and many more uninhabited). But which one to choose? Hedonistic Mykonos, romantic Santorini, or a lesser known one? Or, perhaps, island-hop? A Greek travel enthusiast myself, I definitely prefer island hopping, as this allows me to explore more than one islands each time… but, of course, I still have to make a choice! A couple of years ago, I followed a 13-day itinerary from Santorini to Amorgos, and then to Koufonisia and Mykonos. Certainly, a good place to start (that was my first ever holiday in the Cyclades)! I have been back to the Cyclades several times since, and here is another itinerary to follow.

Day 1 – Piraeus (Athens) to Serifos

Take the ferry from Piraeus (the port of Athens) to Serifos; Seajets and Aegean Speed are the fastest at two hours (approx. 45-50 euros). Renting a car is recommended (in peak season, do this well in advance). In case you’ve decided not to rent a car, there are regular bus services on the island.

The port of Livadi is a lively village home to some excellent waterfront restaurants and taverns. Kali’s is one of the most famous; the dish that really stood out was the salad (Salata Krasiou): green leaves topped with caramelized figs, pomegranate seeds, manouri cheese, and red wine vinaigrette. Another restaurant I’d recommend is Ydrolithos, located on a rooftop terrace. After dinner, have a cocktail at the rooftop bar Shark, or at the Yacht Club, the locals’ favorite.

Day 2 – Serifos

Like with many other Greek islands, Hora is the name of the capital of Serifos. Built on the slopes of a hill, it is a whitewashed village overlooking the port of Livadi and all the while offering panoramic views of the Aegean Sea.

Start your day at Pano Piatsa, Hora’s main square. Here you’ll find the neoclassical town hall and the Greek Orthodox church of Agios Athanasios, as well as colorful chairs and tables from the cozy cafes around the square. The turquoise ones are from ‘Stou Stratou’, the khaki ones from ‘Piazza’; both cafes are excellent choices for breakfast, brunch or coffee. Make sure you try ‘pastaki’, the chocolate dessert that Serifos is famous for.

Pano Piatsa, Hora’s main square, Serifos — Pano Piatsa, Hora’s main square

Then walk up to Kastro (Castle) and to the chapel of Agios Konstantinos to enjoy the most panoramic views of the island.

Then go to the beach. One of the most famous and my personal favorite is Agios Sostis. For this east-facing beach takes its name from the chapel overlooking the small bay. The beach is neither organized nor has any facilities (whether a beach bar, tavern or even a canteen); so make sure you bring a beach towel, a book, food, and water.

Agios Sostis, Serifos — Agios Sostis: my favorite beach in Serifos

Finish off the day where it all started: in Hora. There are several bars here inviting you to join the lively crowd and enjoy a cocktail under the moonlight sky. Vatrahos, Gaidaros, and Aerino are all great choices. In the peak season, some of these bars open early in the day to also serve brunch.

Day 3 – Serifos

Vagia is another beach, located on the south coast of Serifos. Here you can find a small beach bar offering snacks and refreshing cocktails.

In the evening, return to Hora, and take the path that goes down to Livadi. You will pass by a number of blue-domed churches and chapels (I actually lost count). Half-way down, there’s Aloni, a restaurant offering traditional Cycladic food and wonderful views of the port down below. Perfect pitstop to watch the sunset from and enjoy the local cuisine.

Day 4 – Serifos to Sifnos

Take the ferry to Sifnos; Seajets and Aegean Speed are the fastest at 25 minutes (15 euros). Renting a car is recommended (in peak season, do this well in advance). In case you’ve decided not to rent a car, there are regular bus services on the island.

The port of Kamares is a great swimming spot (awarded the Blue Flag) and home to several beach bars; my favorite are the ones further away from the port: ‘Folie’ and ‘Isalos’. I remember early evenings patiently waiting for the sun to dive into the sea, before I did the same myself. All the while, I was downing cocktails listening to Demis Roussos, Brigitte Bardot, and Dean Martin, and secretly wishing I could just be there for the rest of my life…

Day 5 – Sifnos

Apollonia, the capital of Sifnos, is an inland village in the middle of the island, a few minutes drive from the port of Kamares. Steno (which means ‘narrow’ in Greek) is the name of the main (pedestrianized) street, lined with a great number of restaurants and café-bars. It is a wonderful place to kick off your day; however, it is later in the evening when it transforms into a catwalk and really comes alive.

Make your way to the monastery of Hrysopigi (also spelled Chrysopigi), one of the top attractions of Sifnos (it doesn’t take a rocket scientist to figure out why). Built on a tiny islet just off the southeast coast of the island, it is one of the most Instagrammable places on the island. There are several (not organized) beaches on either side of the monastery; the one on the left (Apokofto) is home to the tavern ‘Lempesis’, whereas Saoures on the right is a bit more secluded. Whichever you choose, the beautiful monastery will stand tall in the background.

In the evening, return to Apollonia. With Sifnos being the island of Greek gastronomy, its capital is by no means short of restaurants. ‘Kafeneio Drakakis’ and ‘Tou Apostoli To Koutouki’ are traditional taverns with excellent Cycladic dishes, whereas ‘Cayenne Restaurant Art Gallery’ lies on the more modern end of the spectrum. Both the food and the location are gorgeous. ‘Tou Apostoli To Koutouki’ has a roof terrace offering wonderful views of the Church of Taxiarhes opposite; ‘Kafeneio Drakakis’, on the other hand, has tables off the street perfectly located for sitting back and people watching. As its name suggests, ‘Cayenne Restaurant Art Gallery’ combines gastronomy with art.

Day 6 – Sifnos

Platys Gialos is a large and organized beach (albeit not to the same extent as in Halkidiki) on the south coast of Sifnos. It is home to several beach bars (‘Notos’ was the one I chose and I would recommend), and also to ‘Omega 3’. This is a modern seaside bar-restaurant, amongst the most famous on the island. Fish and seafood may be the stars on the menu here, but items such as sushi and ceviche hint at a departure from traditional Cycladic cuisine. Due to the popularity and the small size of the venue, make sure you reserve a table (or a stool).

In the evening, go to Kastro, a traditional village (dating back to 3000 BC) and the old capital of Sifnos. Sat on top of a hill, it is located 3 km east of Apollonia. Wander around the narrow alleyways and the whitewashed houses (most of them date back to the Venetian times), but make sure you find your way to the Church of the Seven Martyrs, probably the most Instagrammable spot on the island. Sat on a rock, it reminded me of the Church of Agios Ioannis Kastri, on the island of Skopelos, where Meryl Streep got married to Pierce Brosnan in Mamma Mia! Walk around the small church for breath-taking views of the Aegean, before heading back to Kastro to enjoy a meal at ‘Nea Lontzia’ or a mojito at ‘Cavo Sunriso’, an island institution. Then continue to ‘Dolci’ for a late-night cocktail at the bougainvillea-shaded terrace.

the Church of the Seven Martyrs — The Church of the Seven Martyrs

Day 7 – Sifnos

The fishing village of Herronisos (also spelled Cherronisos) on the far north end of the island is not only a fantastic swimming spot, but also home to the waterside fish-tavern of the same name. The winding road from Apollonia offers spectacular views of the northeast coast of the island. From the church of Agios Giorgios on the top of a nearby hill, you can see the island of Serifos; it’s also a beautiful place to watch the sunset from.

The waterside fish-tavern 'Herronisos' — The waterside fish-tavern ‘Herronisos’

Return to Apollonia for dessert and drinks. Stop at the patisserie ‘3 Xanthoi Aggeloi’ for loukoumades (traditional Greek doughnuts, usually served with honey, cinnamon and ice-cream on the side). Then, it’s time for cocktails. ‘Botzi’, ‘Mandolou’, and ‘Doloma’ are intimate all-day café-bars, whereas ‘Argo’ and ‘Cosi’ have terraces with beautiful views.

Day 8 – Sifnos to Folegandros

Take the ferry to Folegandros. On Sundays, Zante Ferries takes the least time (an hour and a half) and is also the cheapest (9 euros). Renting a car is not necessary; there are regular bus services on the island.

Hora, the charming inland capital of Folegandros, will be your base to explore the island. Built on the edge of a 200-meter high cliff, Hora is where the heart of the island beats. Ditch your map (if you have one) and simply wander around the village taking in the friendly atmosphere. Color-coded tables and chairs from the inviting taverns in the squares of the village (see tip 5) provide a picture-perfect backdrop. Then, stroll around Kastro, the oldest part of Hora, before you make your way to the church of Panagia (see tip 2). Some of the houses here are a thousand-year-old.

Dedicated to the Dormition of the Virgin Mary, the whitewashed church of Panagia is the landmark of Folegandros. The ascending path is easy to climb (no more than 15 minutes from Hora), and it will reward you with panoramic views of the island. Evenings are the best time to visit, so you can watch the sunset.

Hora is no short of taverns. One of the most famous is ‘I Piatsa’; it is often fully packed, albeit for a very good reason. It scores top marks on both food and atmosphere.

After dinner, join the millennials for a drink or two in Hora. ‘Baraki’ is a charming cocktail bar, whereas ‘Astarti’ has a more retro vibe; try rakomelo, a traditional alcoholic drink made with raki, honey, and spices (cinnamon and cardamom).

Day 9 – Folegandros

Despite being a small island, Folegandros has a number of beaches perfect for swimming and sunbathing. Unlike Halkidiki, where the beaches are highly organized, or Sifnos, where you will find waterside taverns serving delicious food, beaches here have no such facilities (except for those close to the port of Karavostasis and the coastal village of Agali). So, come prepared. Your choice of beach will depend on the wind, so make sure you ask the locals first.

Katergo can be reached either by boat (10-minute ride from the port) (reason no 1 why this is my favorite beach on Folegandros), or on foot (30-minute walk from Karavostasis). There’s a small islet in the middle of the bay (reason no 2), where you can easily swim and then explore barefoot. Amongst the young crowd, you may spot a few naturalists at the far end of the beach (reason no 3 – I’m only joking!).

Day 10 – Folegandros

You can spend the day on the beach, or you can go hiking. Like Sifnos, Folegandros offers a few designated hiking trails:

From Hora, you can hike to the beach of Fira and then to Agali. On your way there, you will pass by the chapel of Agios Savvas and the church of Stavros. Jumping from terrace to terrace is also part of the route, and as fun as it sounds.

Or, you can follow the donkey trail from Hora to the village of Petousis, and then continue to the beach of Livadi and arrive at the port of Karavostasis.

The trails from Hora to the village of Ano Meria are longer; of those, the trail that passes by the beach of Livadaki is the longest, but very scenic. There’s another, shorter trail passing by the churches of Agia Paraskevi and Stavros.

From Ano Meria, there are quite a few trails worth following. You can walk towards the beach of Agios Georgios (bypassing the church of Agios Sostis), or to the beach of Ampeli (bypassing Agios Panteleimon). Another trail takes you to the beach of Livadaki and then to the Aspropounta lighthouse.

Day 11 – Folegandros to Santorini

Take the ferry to Santorini; Seajets and Golden Star are the fastest at 45 minutes (30 euros).

Get off the beaten track, avoid the crowds, rent a car and drive to Pyrgos Kallistis (or simply Pyrgos), a village built amphitheatrically at the highest point of the southernmost island of the Cyclades. You know what comes next: panoramic views of the whole island (not just the caldera). This is simply the perfect place to watch the sunset that Santorini (or Thira as is also known as) is worldwide famous for.

Afterwards, stroll through the narrow, labyrinthine streets, and then experience the Greek hospitality and local cuisine at Penelope’s Ouzeri, a small traditional eatery, or at Brusco ‘wine. coffee. deli’. Try the ntomatokeftedes (tomato balls/fritters), the locally-produced cheese (hlorotyri) and homemade desserts. Then, go to the SantoWines Winery (another good place to watch the sunset from) and try the island’s wine. Santorini and Vinsanto are both made from the indigenous grape Assyrtiko; the latter is a sweet dessert wine.

Pyrgos, a village built amphitheatrically at the highest point of Santorini

Day 12 – Santorini

Start at the southwest coast of the island. Here you will find the archaeological site of Akrotiri, an ancient Minoan city that had been buried beneath volcanic ash from 1,650 B.C. up until 1967. It is estimated that the settlement was constructed around 4,500 B.C. Get there early to avoid the crowds.

From Akrotiri Beach, you can take a caique to Aspri (White) and Mavri (Black) Beach, or you can walk to Kokkini (Red) Beach and swim at the backdrop of red cliffs.

Then have lunch (fresh seafood of course) at Spilia tou Nikola (The Cave of Nikolas), a seaside fish tavern within walking distance from Akrotiri. Try the locally-produced fava (yellow split-peas) and white eggplants – delicious appetizers not normally found elsewhere in Greece.

In the evening, make your way to Oia, one of the two main settlements on the west coast of the island (Fira is the other one). Built on a steep slope of the caldera, this charming hilltop village is worldwide famous for its sunsets and can often be overcrowded with tourists. Wander around the narrow streets and admire the blue-domed churches before you stop at Atlantis Books, a bookstore that is now considered among the must-visit places in Oia. Panagia of Platsani, Saint George and Panagia Agion Panton are among the most beautiful churches and also worth a visit. Sun Spirit is a good place to sit down, enjoy a cocktail and watch the iconic sunset.

Day 13 – Santorini

Wake up early and stroll around Oia first thing in the morning, as this is when it tends to be at its quietest.

Go swimming in Vlyhada, a beach on the south coast of the island, where you can also have lunch at one of the waterside taverns around the picturesque harbor. Then have a cocktail at Theros Wave Bar, an all-day beach bar.

In the evening, go to Fira, another hilltop village on the west coast of the island. Escape the crowds and walk along the caldera-edge pathway towards the villages of Firostefani (15-minute walk from Fira) and Imerovigli (half an hour walk from Fira). Watch the sunset at the small church of Agios Georgios, or at Volkan On The Rock, a café-bar that serves coffee, as well as excellent food and cocktails (the menu is by Ergon Greek Deli & Cuisine). You can even watch a movie there, at the open-air cinema.

Another open-air cinema is Kamari, situated in the village of the same name, on the east coast of the island. Watching a movie under a sky full of stars is one of my favorite things to do in Greece in the summer, and I would highly recommend you try it.

Finally, have dinner at Metaxi Mas, a restaurant at the inland village Exo Gonia, that many consider the best one on the island. It may not be on the cliff edge, but it still offers panoramic views.

After dinner, go back to Fira, to the Kira Thira Jazz Bar.

Day 14 – Departure from Santorini

All good things come to an end, and so does this holiday. If this was your first time island-hopping in the Cyclades, I’m pretty sure it won’t be the last. Check out another 2-week itinerary around the Cyclades here.

How to get there

If you follow this itinerary, you’ll need to fly to Athens (it’s always worth spending a few days there too), then take the ferry to Serifos from Piraeus (the port of Athens).

Check out the ferries timetable here. The Eurail Greek Islands Pass is worth considering.

From Santorini, you can fly to Athens or to many European destinations, or take the ferry back to Piraeus.

When to visit the Cyclades

For me, the best time to visit the Cyclades (and the Greek islands in general) is the summer; this is when the ferries are at their most frequent, the weather at its warmest and the atmosphere at its best. July and August are the best months. However, avoid late August when the winds get too strong.

Accommodation

Serifos

Hotel Rizes and Coco-Mat Eco Residences stand out. Alternatively, rent a room or a house in Hora.

Sifnos

Apollonia is the most convenient place to stay; you could rent a room or a house/apartment there.

Folegandros

Hora is the best place to stay; you could rent a room or a house/apartment there.

Santorini

Accommodation in Santorini can be quite expensive. If your budget allows it, why not choose one of the 59 hotels with an infinity pool on the edge of the caldera. These are located on the west coast of the island (Oia, Fira, Imerovigli, Firostefani). Even if you cannot afford to stay in one of these luxurious hotels, I would strongly recommend you stay on the west coast.