A Shoulder Season Excursion to the Greek Islands

Our trip began in the charming town of Chania on Crete, an easy 1-hour airplane ride from Athens. Chania features a 16th-Century Venetian lighthouse, lots of seafront restaurants, including the highly recommended Neoria Fish Tavern, and pleasant shopping streets.

Next on the agenda was a drive to the isolated town of Hora Sfakion and its neighboring village of Loutro -- which is reachable only by boat or footpath. Great places for a relaxing day or two with the opportunity to explore hiking trails close by. A rental car is useful to get there, but a variety of tour services can also be used.

Stops in Reythmno and Herkalion completed our Crete experience. Reythmno is a pleasant, tourist-oriented town which also is home to the University of Crete, so there is a lively student presence. The Melrose Hotel was reasonably priced and offered very nice rooms, a substantial breakfast, and an absolutely outstanding staff. To Pigadi restaurant in town is well worth a visit. In Herkalion, the Archeological Museum has an amazing array of relics from as far back as 4000 BCE, including the Phaistos Disc, an as-yet untranslated text from around 2000 BCE. The nearby excavation at Knossos is also worth a visit.

A ferry ride to Naxos followed (with a stop in Santorini to change ships). The boarding process for the ferries can be chaotic, with crowds of people and cars and trucks all swarming to the ship. But don't worry, everyone gets on and the ferry rides are comfortable with airline-style seats and plenty of amenities on-board.

Naxos is a mellow island, with stunning sandy beaches just outside of the port and a series of beautiful hillside villages that can be visited on a tour or with your own rental car. 1926 Taverna Naxos is right in town and has absolutely spectacular food and the usual gracious and relaxed service that is the hallmark of Greece.

If you have any questions about potential adventures in Greece, let me know and I will be happy to be of help. From boutique hotels in town to gorgeous resorts, there are a wide variety of hotel options for any trip.

The Greek Islands provide a huge variety of potential experiences, from the party world of Mykonos to the very mellow scene of Naxos or Ios. Shoulder season (May or October) lets you experience the islands with smaller crowds but with most services fully open for business. But if you can only go in the high season, there are still spectacular sunsets awaiting you.

This trip report is part of our ongoing series on travel to Greek Islands, Greece. In need of further inspiration? Check out Artemis Koutsogiorgas’s guide, Your Guide to a Dreamy Greece Honeymoon.