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Winter Island Hopping: best islands

Crete ● Naxos ● Santorini ● Syros ● 01 January 2018

Island Hopping is not only for summer. Travelling in low season has many advantages, such as great accommodation deals, uncrowded places, relaxing atmosphere and time to explore every corner of the new destination. There are many Greek islands for winter that can offer you super moments. Besides, the weather is calm even in January and February, and especially in Cyclades and Crete, the chance of rain is very low. Thus, winter island hopping is a top experience for the new year. Have a look at these Greek islands that are beautiful during winter and pack now your suitcase!


Syros and its main town Ermoupolis is the capital of Cyclades. It is a large city that has many possibilities for entertainment. Restaurants, cafés, bars, shops and museums are open all year long as Syros is a vivid city. Plus, walking around the paved streets of Ermoupolis, where you will be impressed by the neoclassical houses, the imposing mansions and the buildings designed by the famous architect Ernst Chiller is enough to spend an interesting day.


After Syros, you can go to Naxos, the largest island of Cyclades, which is also a vivid Greek island. In Naxos, you can stroll around the castle and Chora and eat in the topical taverns, whose Greek cuisine is renowned all over the world. Naxos has also many beautiful inland villages, where during the off-season you will have the chance to talk to local people and feel their authentic aura. Furthermore, Naxos has significant archaeological sites and museums, such as Portara at the port, the Archaeological Museum and Kouros statues, which will turn your vacation into cultural holidays.


Two hours by boat from Naxos, you can reach Santorini, the Greek island that constitutes a totally new chapter in the book of your vacation in Greece. Santorini is very touristic during summer, and thus many shops, restaurants, bars and hotels are closed from November to April. However, Santorini has so many touristic facilities that you can easily find top accommodation to stay, which will also be much more affordable than during the high season. Moreover, you will enjoy this spectacular island away from the crowds of tourists, feel its captivating character together with local people and enjoy Oia and Fira without having to walk near thousands of travellers. Santorini has also interesting museums, such as the Archaeological and the Prehistoric Museum, as well as the ancient site of Akrotiri.


A few hours by boat from Santorini, is located Crete, which is definitely an ideal Greek island for winter. Crete has 4 large towns (Chania, Heraklion, Agios Nikolaos and Rethymnon), major ancient sites, such as Faistos and Knossos, numerous traditional seaside and mountainous villages, as well as verdant nature, rivers, gorges and mountains with wonderful hiking paths. Crete is also one of the southernmost spots of Europe, and thus its weather is mild. That means that in the spring you can definitely sunbathe and -why not- swim in the Libyan Sea.

Where to Stay

Hotel in Chania , Greece Hotel Idramon
8.4 10
Hotel Idramon
Mitropoleos square, 73100 Chania , Greece

Hotel Idramon is set in a traditional building in the historic center of Chania, just 500 meters away from the Venetian Port and 15 minutes walk from the sandy beach of Nea Chora. Chania International Airport is 17 km away.

Appartment in Paros, Greece Fivos Apartments
8.4 10
Fivos Apartments
Aliki, 84400 Paros, Greece

Fivos Apartments is located in Aliki Village, just 5 minutes walk from the beach. Paros National Airport is 3.5 km away from the property, while Paros Port is at 12 km.

Hotel in Tripoli, Greece Arcadia Hotel
Arcadia Hotel
Kolokotroni Sq., 22100 Tripoli, Greece

Arcadia Hotel is located in a very central location in Tripolis. Its location is an excellent starting point for guests who wish to explore Peloponesse. Kalamata International Airport is 76 km away.