10-Day Cyclades Island Hopping Itinerary - Greece

While many travelers stay in the cozy but touristic Plaka, we opt for the less busy, hip Psiri district where the Athenians also like to come. You sleep in a trendy hotel but are still within walking distance of Plaka and Monastiraki. You wouldn’t know it now, but this originally working-class neighborhood used to be the slum of Athens, it’s changed a lot and is now full of street art, old craft shops, vintage shops, atmospheric restaurants and trendy bars. Besides walking, the metro is the perfect way to explore Athens and is even adorned with archeological finds discovered during its construction. Head to the parliament building or the Acropolis Museum, one of the highlights of Athens. At the foot of the Acropolis is the Dionysus Theater, the oldest theater in Europe.

Today you’ll take to the sea and sail to Naxos, the largest Cyclades island, where we’ll arrange a transfer for you to your family run hotel just south of Naxos town. Within walking distance you will find the most beautiful sandy beaches, which is most people’s main reason to come to Naxos. In the evening, you have a variety of Greek cuisine at your mercy, from the meaty delight of pita gyros, freshly prepared fish or a salad bursting with locally-sourced feta.

You’ll have the next couple of days free to do as your please, so after breakfast this morning, put your feet up, relax and unwind on the wide sandy beach that’s just minutes from your hotel. Sit with a cooling iced coffee in hand, feeling like a Greek God and maybe even treat yourself to a Loukoumadis – a kind of Greek donut. The following day, head out to discover the beauty this island has and take a fulfilling hike. Unlike most other parts of the Cyclades, the interiors of Naxos are rich with vegetation, making it a hiker’s paradise with stunning views throughout. Rent a car and drive into the interior in search of small, traditional villages, including Filoti with a cozy village square and Apiranthos where backgammon is often played in the street.

On arrival, our local representative will hold a sign with your name on it and take you to the port capital, Fira. Perched on the edge the volcano crater and its 270 meter high cliffs, this is the perfect base to explore from. After you’ve taken your things to your room, you’ll probably feel like a refreshing dip in the pool to cool off. In the evening, you can stroll through the attractively lit streets of Santorini and then have a bite to eat at one of the tucked away tavernas on a small side street.

Spend the next few days avoiding any crowds and explore the island by rental car. Oia is an authentic Greek town where you can spend hours aimlessly strolling through the narrow streets past beautiful houses. You can also tour around the less discovered spots of Santorini, passing forgotten villages in the interior, excavations in the north and lazing on a deserted black-sand beach in the south. If you fancy something more adventurous, take a day trip to the volcanic island of Nea Kameni and walk to the sulfur fuming crater. Alternatively, use this geothermic activity to relax in the hot springs on the island of Palea Kameni, only a short boat trip away.