Two Weeks in the Greek Islands Itinerary: Island Hopping in Cyclades

Dramatic landscapes, white-washed villages and stunning beaches – the beauty of the Greek Islands lure thousands of tourists each year. Among the most popular are the islands in Cyclades, a large group of islands in the southern Aegean Sea. The Cyclades, which includes the famous islands of Santorini (Thira) and Mykonos, refers to the Greek islands which form a circle around the sacred island of Delos. If you are still wondering what to add to your itinerary for Greece, the islands of Cyclades will not disappoint.

There is a lot of variety in this island group, from history to hiking, indulging to relaxing. Depending on how much time you have, you can easily visit different Greek Islands during one trip. We spent two weeks in the Greek Islands (during low season), focusing our itinerary on Cyclades, where we travelled by ferry from one island to another. Here are the different Greek islands that we visited in Cyclades:

Two Weeks in the Greek Islands Itinerary

Santorini

With its idyllic villages perched on cliffs overlooking the caldera, Santorini is undoubtedly the most picturesque among the Greek islands in Cyclades. Santorini offers a glimpse of the island’s volcanic past with its colourful beaches (red, white and black) and incredible geologic scenery. Embrace the stunning views of the Aegean Sea and explore the unique landscape of Santorini by taking the 4-hour walk from the main town, Fira to the sunset town, Oia.

READ MORE: The Contrasting Colours of Santorini: A Dream Destination

Ios

Famous among young people as a party island in the summer, Ios is known for its captivating beaches and wild nightlife. During our visit in the low season however, we saw a completely different scene – the beaches were nearly deserted. Despite the lack of activity, we actually enjoyed the laid back atmosphere. Have you partied in Ios or visited in summer?

If you end up partying in Ios during summer, make sure you add Mykonos to your itinerary. Mykonos is considered one of the most beautiful party destinations in the world. During low season, the ferries, unfortunately, didn’t go  as frequently to Mykonos so we didn’t have to chance to see it. Have you been to Mykonos during summer? What was it like?

Naxos

Upon entering the port, Naxos instantly enthralls its visitors with its iconic marble gate, Portara (a 6th century BC temple of Apollo) and its white-washed main village, Hora (hora is often used to refer to main town of a Greek island). The largest and greenest island in Cyclades, Naxos is home to fertile valleys, traditional villages and impressive mountain scenery. There are apparently a lot of good hikes on Naxos but we didn’t have the time to do them.

Naxos also had some of the best beaches we’ve visited in the Greek Islands. While we didn’t have time to see other villages, we had a great time with the locals while we were in the main village of Naxos. Near the port area of Hora, we enjoyed delicious souvlaki (small pieces of meat grilled on a skewer) and tried the famous raki (a traditional alcoholic beverage in Greece).

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Paros

The charm of Paros lies on its towns and villages. Wandering through the traditional fishing village, Naoussa and its beautiful capital, Parikia were some of the highlights of our trip to Paros. Apart from the nice beaches and white-washed houses, the island also has historical landmarks worth exploring. In Naoussa, it’s hard not to miss the remains of the Venetian Castle, a 15th Century fortified building. In Parikia, make sure to visit the historic Byzantine church complex, Panagia Ekatontapyliani (also known as Our Lady of the Hundred Gates).

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Antiparos

Picturesque little seaside bars and cafes welcome you as you set out into Antiparos. This island has nice beaches and has a more laid back atmosphere than Paros. Spend the day searching for celebrity houses (Tom Hanks apparently owns a property here) or simply wandering around its beautiful villages. If you have more time, make sure to visit the Cave of Antiparos which is the most popular site on the island (The Cave of Antiparos is open from April to October).

Map of the Major Islands in Cyclades, Greece

Getting In and Around the Greek Islands (Cyclades)

The islands are all linked by ferries to each other and to Athens in the mainland. Prior to your trip, check the ferry schedules online then confirm the details upon your arrival in Greece. Note that the port in Athens is called Piraeus. For our two week in the Greek Islands, we booked our ferry tickets ahead online with Blue Star Ferries. It’s a lot cheaper if you book your tickets a few weeks in advance. To give you an idea of the ferry ticket prices, the longest ferry ride we had was from Piraeus to Santorini, which took 8 hours and set us back €30 per person for economy class.

If you have more budget and short on time, you can also consider flying to the islands from Athens. There are airports on some of the bigger islands such as Mykonos, Naxos, Paros, Santorini, Syros and Milos. Some airlines even have direct flights from different parts of Europe to Santorini and Mykonos.

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When to Visit the Greek Islands

High Season in the Greek Islands is from July to September. During this time, the weather is hot and sunny and sea is warm and perfect for swimming. Expect lots of tourists and high prices for accommodation. If you’re looking to party, this is the best time to go.

Low Season in the Greek Islands is from November to April. You can save a lot of money during winter season as there are fewer tourists. Due to the lower demand, accommodation is cheaper. However, many hotels and restaurants are closed during this time and some ferry routes have limited schedules or don’t run at all. The weather in the Greek Islands is still warmer than other parts of Europe but the sea is a littl cold for swimming.

We went during low season and it was indeed very quiet. If you are travelling alone it can be way too quiet but since we travelled as a couple, we enjoyed the laid back atmosphere of the Greek Islands during winter.

Shoulder Season in the Greek Islands is from May and June, September and October. This is a great time to go considering lesser crowds and good weather. Everything is also open and ferries run nearly all of their routes.

Have you visited the Greek islands? What are your favourite islands in Cyclades? Do you have anything to add to our two weeks in the Greek Islands itinerary? Let us know.

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