An offseason adventure through the Greek Islands

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. 

• 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. 

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. 

• 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. 

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. 

• 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. 

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. 

• 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.