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An offseason adventure through the Greek Islands

Rachel Schnalzer, Senior Writer

June 26, 2024

“Time passes like water here,” said the taxi driver as he deftly navigated the twists and turns of the arid road leading up from the Port of Santorini. 

 

Five Eurail colleagues and I had just disembarked from our fourth and final ferry ride of our offseason trip to the Greek Islands.

...



We already missed the mellow pace of life on Syros, Paros and Naxos, yet eagerly anticipated our chance to discover the white-washed villages and sapphire ocean views surrounding Santorini. 

After our experience hopping from island to island, I agreed with our taxi driver — time felt precious in the Cyclades. There were quiet moments when time stood perfectly still and others when the hours slipped away like seawater into the waves. 

In this itinerary, you’ll learn how to use the 4-day Greek Islands Pass to explore the Cyclades for yourself. We spent most of our time in the port towns, but remember – the islands hold endless gems to experience, especially when you venture off the beaten path during the offseason.

Buy your Pass, make your ferry reservations, and, no matter what time of year you visit, pack some sunscreen. The Greek Islands are calling. 

  1. Athens, Greece 🇬🇷
  2. Syros, Greece 🇬🇷
  3. Paros, Greece 🇬🇷
  4. Naxos, Greece 🇬🇷
  5. Santorini, Greece 🇬🇷

Trip details

The coastline in Syros

Syros, Greece

Why it's worth visiting:

Just four hours by ferry from Athens, stunning Syros provides a laidback start to your island-hopping adventure.

 

We stored our luggage for a small fee at the Syros Port Passengers Station, and within minutes were in the middle of Ermoupoli, searching for sunhats, books, and other island essentials in the town’s small, locally-owned shops. 

 

What to do:
  • When you arrive in Ermoupoli, you’ll see a blue-domed building — the Church of the Resurrection of Christ — beckoning from atop the hillside. In the morning, before the island heats up, take a walk up to the church and experience a quieter, more residential side of the port town.
  • After your hike, take a dip in the sea at Vaporia Beach and catch sight of the cliffside homes and Church of Agios Nikolaos perched above the water. 
  • Before boarding your next ferry, take time to relax at one of the charming cafes that line Peloponnisou, a narrow lane shaded by fuchsia bougainvillea growing overhead. 

 

Suggested route
  • From: Piraeus Ferry Terminal
  • To: Syros 
  • Average travel time: 4h 
  • Transfers: 0
  • Seat reservations: Required
tip-image
View train connections and reservation options in the timetable.
Ruins of the Temple of Athena in Paros

Paros, Greece

Why it's worth visiting:

Parikia, the main port of Paros, is a lively place, even after its famous sunsets fade into night. Still, there are plenty of quiet moments to enjoy in the busy town – from getting an up-close look at ancient history to relaxing in its tranquil blue waters. 

What to do:
  • Paros boasts several pristine beaches, but when it comes to convenience, Livadia Beach is hard to beat. The gentle waters, accessible with a 15-minute walk from the port, look almost impossibly clear. 

  • Nearby the ferry port are the remains of the Archaic Temple Of Athena, built in the sixth century BCE. The short but steep set of stairs leading up to the temple ruins offer a lovely view of the port and surrounding white-washed homes.   

  • Dive deeper into ancient history with a visit to the Archaeological Museum of Paros, which showcases finds from excavations conducted in Paros and nearby islands. 

Suggested route
  • From: Syros
  • To: Paros
  • Average travel time: 1h 
  • Transfers: 0
  • Seat reservations: Required
tip-image
View train connections and reservation options in the timetable.
Bird's eye view of white-washed buildings in Naxos

Naxos, Greece

Why it's worth visiting:

An enormous, marble gate – the only remaining part of a temple dedicated to Apollo, built in 530 BCE – greets travelers as they dock in the port of Naxos Town.

 

Home to a castle and significant archaeological sites, there are plenty of major attractions in Naxos – but make sure to experience the smaller gems hiding in plain sight, too. 

What to do:
  • Start your day by sampling Greek pastries at Sitári Shop, a jewel among Naxos’ plentiful bakeries. Don’t miss the baklava cookies, drizzled with honey and dusted with cinnamon. 

  • Pick up a book to read at the beach at Papyrus, a secondhand bookshop with a wide selection spanning at least 10 languages. There’s a jewelry section at the back of the store – and a “secret” door that leads to a winding pathway up to the Venetian Castle of Naxos.  

  • Cool off with an afternoon swim at Agios Prokopios Beach. Keep your eyes peeled for marine life and maintain your distance – on a morning swim, I saw a sea turtle swimming out to sea. 

Suggested route
  • From: Paros
  • To: Naxos
  • Average travel time: 45m 
  • Transfers: 0
  • Seat reservations: Required
tip-image
View train connections and reservation options in the timetable.
Close-up of a blue-domed church in Santorini

Santorini, Greece

Why it's worth visiting:

Welcome to our final stop: world-famous Santorini, the grand dame of the Cyclades. Though some parts of the island attract heavy crowds, offseason travelers can easily find mellower places to pause and reflect on their Greek Islands adventure. 

What to do:
  • Akrotiri, a vast archaeological site considered to be Greece’s version of Pompeii, is one of the most well-known places on the island. I recommend visiting around golden hour, when crowds flock to Oia and Fira for sunset. On a balmy, offseason evening, my fellow travelers and I had the ancient site almost entirely to ourselves. 

  • When it comes to Santorini’s beautiful white-washed towns, I favor Pyrgos, the highest village on the island. Sometimes skipped by travelers, Pyrgos is a place to unwind as you explore its narrow passageways, stairs and lookouts.   

  • Santorini’s sunsets are famous for good reason — but don’t forget to wake up early at least one morning during your trip to experience the sun rising over the eastern sea, gradually bathing the island in light. 

Suggested route
  • From: Naxos
  • To: Santorini
  • Average travel time: 2h 
  • Transfers: 0
  • Seat reservations: Required
tip-image
View train connections and reservation options in the timetable.