Greek Islands Itinerary
There are many individual ways to discover the Greek islands. However, if you could use a little guidance and want to explore the islands beneath the surface, this is the itinerary for you. With destinations bringing you the finest in historical architecture, low-key nightlife, delicious food and even windsurfing, we guarantee you a brilliant experience in your hands when you grab one of our Eurail Passes.
The Eurail Greek Islands Passes offer you two different ways to explore the majestic islands of the Aegean. One includes transfers to/from Italy and one is strictly for domestic travel between Greek Islands. Both Passes also give you a 30% discount on any additional ferry trips operated by the Attica Group during the validity of your Pass.
This is the jumping-off place for your trip, with ferries leaving from Piraeus harbor. Athens itself has a million attractions, so try to spend some time here before embarking on your journey. Stop at the Acropolis, the most important ancient site in the Western world, standing over Athens and visible from almost anywhere in the city.
Visit the Parthenon temple - meaning virgin’s apartment - built in the name of the goddess Athena and embodying the power and prestige of the city. Or go watch a film at Cine Paris, the first outdoor cinema in Athens established in the 20s on a rooftop in Plaka.
Island #1 - Syros
Syros is where you would go for a chilled out time as it has this relaxing family island vibe. As one of the only places in Greece to have experienced the Renaissance, it offers architectural gems such as the Ermoupolis city hall and the Apollo Theater, home to the island’s various cultural events, performances and operas.
If you’re in Syros, beach days are a must-do. We recommend the northern beaches but don’t hesitate to see it all. Drop by Plakostroto - a rustic tavern that serves local dishes - and enjoy delicious veggies and herbs grown by the tavern itself. Talk about refreshing!
Island #2 - Naxos
The biggest and greenest island in the Cyclades, Naxos is a gem infused with golden beaches and magnificent historic monuments. Take a trip to Portara (the great door), which used to be a temple devoted to the god Apollo and is proudly standing 2500 years later. The Chora Castle is another must-see. It’s quite a walk, so bring your water and a camera to capture the multitude of restored chapels.
If you’re craving a rush in the midst of your zen holiday, why not go windsurfing. With its shallow lagoons and great wind conditions, make sure to hit up Laguna, Agios Georgios or Plaka beach for an adrenaline-filled treat.
Island #3 - Sifnos
Sifnos is one of the greatest examples of Greek island culture with its perfect balance of beaches, nightlife, traditional architecture and - by apparent consensus - the best food in all of the Cyclades.
The most popular beaches are on the southern side of the island and are equipped with heaps of tourist facilities. There you can also visit the Monastery of Chrissopighi, the “protector of the island”. After a long day of tanning, exploring and learning, spend your evening enjoying the delicious food and the even more delicious attitude of the friendly locals.
Island #4 - Crete
While you’re here, give the “cradle of Minoan civilization” a tour with a visit to the Heraklion Archaeological Museum. In the historic realm, check out the Palace of Knossos for insights into Europe’s oldest city and to explore the largest Bronze Age archaeological site on Crete.
If you find yourself in Chania, make sure to visit the Old Venetian Harbour, filled with cafes, bars, restaurants, and bakeries. If you’re going on a family trip or simply have an interest in aquaculture, pay the CretAquarium a visit - with 200 different species it's the largest marine research complex in the Mediterranean.
Good to know...
Direct flights to Crete's airports are only available during high season (May/April - September/October)
Santorini and Mykonos airports are an option, but they have less direct international flights than Crete.
International flights are cheaper from Athens, but it will take one of your ferry trips to get back there.