14 Day Cycladic Island Hopping Itinerary 

Greece is the perfect place to experience island hopping with its endless array of islands. There are 227 inhabited Greek islands which can make it tricky to choose from as they each offer a unique landscape and atmosphere. In this guide you will discover the best Cycladic islands to visit over a 12 day stay, including some of the best places to visit, stay and eat at on each island. 

The Cyclades are a group of islands located in the south-east of the Aegean Sea. The islands are most known for their volcanic landscapes, sandy beaches, and whitewashed architecture. Even though the Cycladic islands are one of Greece’s most popular destinations, many islands remain unknown to many tourists. To maintain balance, I have focused the guide on the most popular Cycladic destinations as well as islands off the beaten track.  

Weather

The weather in the Cycladic islands is Mediterranean with dry summers and mild winters. The best time to visit the Cyclades is between May and October to avoid rain. The hottest months of the year are July and August with an average temperature of 24 degrees Celsius in the month of July. The summer months tend to be packed with tourists so if you are interested in avoiding the crowds the best months to visit the Cyclades are June and September. The weather tends to be less extreme in these months and the accommodation as well as flight prices are usually lower than in high season. 

The Meltemi winds are north-westerly winds characteristic to the Greek islands during the summer months. The winds are strong and dry, helping bring down the temperatures on the Cycladic Islands to a bearable level. However, they may sometimes cause ferry delays which is why travel insurance is a necessity when island hopping in the Cyclades. 

Ferries

There are several different ferry companies to choose from when planning an island-hopping holiday in the Cyclades. These include Sea jets, Blue Star Ferries, Minoan Lines, Fast Ferries, Golden Star Ferries and Zante Ferries. Sea jet ferries are the fastest option; however, the price of the tickets is also higher. The most popular option is Blue Star Ferries whose tickets vary in price depending on the class chosen.  

I would highly recommend buying a ticket with a numbered seat instead of economy if choosing Blue Star Ferries, especially for longer journeys as the ferries get very crowded during the summer months and finding a seat may be difficult. If you are a student, purchasing a digital ISIC card can save you 50% when travelling on any of the Greek ferry lines. The ferry tickets can be purchased directly from the official websites as well as from third party providers such as: 

  • Goferry.com 
  • Ferryhopper.com 
  • Directferries.com 
  • Ferries.gr 
  • Greeka.com 

Interrail Fairy Pass

Another option worth exploring is the Interrail Greek Ferry pass which can be purchased on the interrail.eu website. There are two options when buying a ferry pass which include a 4 day and 6-day pass. Both passes can be used on any day within 1 month, with an unlimited number of journeys per day. The pass can be purchased in first and second class and discounts are provided for people between the ages of 12 and 27. The four-day pass is available in a mobile version, while the 6-day pass is delivered to your address. It is important to buy the physical 6-day pass at least one month in advance of the trip to ensure that it is delivered in time.  

Plane

The fastest way to reach the islands is by plane which takes between 20 minutes to an hour. However, it is important to bear in mind that not all the islands have an airport. The flights to the Cycladic islands are typically taken from Athens and islands such as Mykonos, Santorini, Naxos, Milos, Syros, Rhodes, Crete, Astypalaia, and Paros. There are many airlines to choose from when flying from Athens to islands with international airports. Olympic Air and Aegean airlines offer several flights to the Cycladic islands each day. A recent addition is Fly Cycladic which is an airline dedicated to island hopping. It is best to book the flights directly from the airlines instead of third-party providers. 

Public Transport

The easiest way to get around Athens is by train and metro. The ISIC student card provides a 50% discount for students travelling by train from the airport to the centre of Athens. When it comes to transport on the island’s buses are often frequent and reliable even on the smaller Cycladic islands. However, if your goal is to visit destinations off the beaten track renting a car, scooter or ATV is a good option. Prices tend to be lower when bookings are made in advance. It is important to note that a credit card and a full driving license is needed to rent all forms of transport including scooters and ATVs in Greece. 

The Itinerary

Day 1-2: Athens

Athens is the perfect place to begin your island-hopping itinerary as all islands can be reached from here. Athens has three ports including Rafina, Lavrio and Piraeus which is the biggest port in all of Greece. Both domestic and international flights can also be taken from the El. Venizelos airport located just outside of Athens.  

Things to Do

The Parthenon

The Parthenon is a must-see attraction in Athens. The temple is located in Acropolis, right in the heart of the city centre. It is dedicated to the Greek Goddess Athena Parthenos and was built in the mid-5th century BC. The temple served many religions over the years, originally being used to serve ancient Greek gods. During the 5th century AD it became a Christian temple dedicated to Hagia Sophia and the Virgin Mary. It was eventually used as a mosque during the Ottoman Empire. The Parthenon is now an open museum and is no longer used for religious purposes. 

The Parthenon is definitely worth a visit even for the view of Athens seen from the top of Acropolis. Many other monuments can also be found near the Parthenon such as The Odeon of Herodus Atticus, the Theatre of Dionysus, The Temple of Athena Nike and The Erechtion. The tickets can be purchased either online or on the spot, with combo tickets available that allow entry into all sites. It is important to bear in mind that the walk up to the Acropolis is quite steep and the path can be uneven at times. It is best to plan your visit in the early morning to avoid crowds and high temperatures.  

Plaka

Plaka is a colourful and picturesque neighbourhood in the centre of Athens. It is worth a visit during your short stay in Athens to explore the various tavernas, cafes, boutique hotels and souvenir shops lining the narrow streets. Plaka is the oldest district in Athens and has a long history dating back to ancient times. During the Ottoman Empire the district was known as the Turkish quarter which is why many of the buildings such as the Fethiye Mosque feature architecture dating back to this time. In general, the buildings found in Plaka showcase a neoclassical style. 

Plaka is located right next to the Acropolis which makes the two areas easy to visit in one day. Many museums are also located in the vicinity such as the Frisirras Museum, The Benizelos Mansion, Museum of Pavlos and Alexandra Kanellopoulou, The Athens University Museum and The Jewish Museum just to name a few. The Roman Agora built between 19-11 BC is also situated near Plaka and is worth a visit. If you are interested in shopping, Plaka has a wide selection of artisan goods such as high-quality Greek olive oil, soaps, ouzo as well handmade jewellery. 

Day 2-5: Syros

Ermoupoli

The first stop on the itinerary is Syros, the administrative capital of the Cyclades. Syros is a lesser-known Cycladic Island which has allowed it to remain unspoilt. It does not resemble what first comes to mind when thinking about a Cycladic Island due to its Venetian architecture. Ermoupoli which is the capital of Syros was built as an extension to the medieval settlement of Ano Syros built by Venetians in the 13th century.  

The picturesque town is full of narrow alleyways dotted with small souvenir shops, cafes, and restaurants. The focal point of Ermoupoli is The Town Hall and Plateia Miaouli where most of the venues can be found in the streets leading out of the main square. The blue domed Agios Nikolaus church, the Agios Georgios Cathedral and the Apollon Theatre are one of the most iconic monuments on island and a must see for all visitors.  

Beaches

When in comes to beaches, Syros boasts an array of options. Galissas in the West of island is situated in a sheltered cove and features crystal clear waters. Kini is another popular beach near Ermoupoli that is also the location of the island’s top seafood tavernas. Finikas although slightly crowded in peak season as well as Delfini which is more secluded are also worth a visit. 

Day 5-10: Naxos 

The second stop on the itinerary is Naxos which is the Cycladic Island. Although not as popular as Santorini and Mykonos, the island is slowly gaining popularity amongst travellers. The island is characterised by its roofless whitewashed buildings decorated with blue windows. Most of the traditionally built houses on the island can be found in the Kastro which is the old Venetian town of Naxos (Chora). Inside the Kastro, narrow alleyways called sokakia can be found, showcasing a multitude of small shops, churches, mansion houses and tavernas. 

I would recommend renting a car, scooter, or ATV for your stay in Naxos as it allows for easy transportation to some areas that may be difficult to reach using a bus. To avoid paying a high price for accommodation, I would advise staying outside the Town of Naxos if renting a vehicle is an option. 

What to Do 

Old Market and Port 

Visit the Old Market in the Old Town of Naxos and wander around the winding alleyways to discover an array of artisan shops selling handmade jewellery and art pieces. Explore some of the best tavernas in Naxos hidden in the maze that is the Old Market. Even though, Naxos is not known for having a very prominent nightlife scene, the port is still a hotspot for some of the best bars and restaurants on the island. Although bear in mind that the prices tend to be higher here than in the streets leading away from the main port of Naxos. 

Beaches 

Naxos offers some of the best beaches in the Cyclades with their soft sands and crystal-clear waters. Agios Georgios beach is located in Naxos Town; however, it tends crowded during the summer months. It is a great beach for families as the water is shallow and a number of tavernas, bars and cafes can be found here as well. Another popular beach near Naxos Town is Agios Prokopios which is surrounded by a variety of venues as well providing the option of renting a sunbed. If more secluded beaches are your preference, Plaka, Mikri Vigla and Alyko are all must see beaches. 

Mountain Villages 

In the centre of Naxos, you will find mountains with miniature quaint villages dotted across the landscape. Both Apiranthos and Halki are worth exploring during your visit to Naxos. The villages are approximately a 30-minute drive away from Naxos (Chora), offering stunning panoramic views of Naxos along the way. If you are unable to rent a car for your trip, bus tours of the island which feature the mountain villages of Naxos can be purchased instead.  

The villages showcase Venetian style buildings and towers covered in brightly coloured flowers and ornaments. While in Apiranthos, it is worth visiting the church of Panagia Apirathitisssa, the Archaeological Museum, the Museum of Folk Art or the Geological Museum. Meanwhile, Halki is famous for its Byzantine churches and Kitro liquor produced at the Vallindta distillery. The distillery is open to the public and provides free samples. Even though the village of Halki is quite small, the cafes and tavernas offer some of the best food and drink on the island.  

Day 10-12: Santorini 

Santorini is the most popular Cycladic Island, followed closely by Mykonos. The island is known for its wide offer of boutique hotels and is known as a luxury travel destination. The main towns in Santorini are Fira, Oia and Imerovigli. The prices of food accommodation, food and beverage is amongst the highest in the Cycladic islands, particularly the closer a venue is to the Caldera. However, it is still possible to visit the island on a budget. To get the best prices, book your accommodation several months in advance. Another option is booking your stay in Karterados which is the closest area to the town of Thera. It is only a 10-minute bus ride away and offers a multitude of accommodation options at a fair price.  

Thera 

Santorini is a destination highly worth visiting for the incredible views from the Caldera. The Caldera itself is a volcanic depression which collapsed following an eruption during the Minoan era. Besides the incredible views, the streets of Fira are where you will find beautiful chalky Cycladic style buildings, cobblestone streets and the azur coloured dome of the Three bells of Fira. The Museum of Prehistoric Thera, the Cathedral of Saint John the Baptist, the Orthodox Metropolitan Cathedral, The Mati Art Gallery and the Old Port are all also all a must see. 

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