Traveling in Greece: A Greek Isles Odyssey

It took Odysseus ten years to sail from Troy back home to Greece. That seemed way too long back when we spent half a semester getting through The Odyssey. Now, though — after having been lured, lulled, and enchanted by the Greek Isles myself — I get how that could happen.

Across every emerald/sapphire/aquamarine strait, I’d spot another fine-looking island that I just didn’t have time for. Watching the sunset on a terrace in Santorini, my friend Manos would worry that I hadn’t seen Delos. “How could you not see Delos?” On Crete, 80-something George took a break from crafting phyllo dough to half-whisper, “The citron! You must taste the citron of Naxos.” Fired up by all of that sound advice and abundant temptation, we’ve tweaked our itinerary in the Greek Isles to include more islands, the finest sites of antiquity, white beaches beyond compare, and time with our friends everywhere who insisted that we bring you for a visit.

You start in Crete where the aforementioned George is the last baker on the island who makes tissue-thin phyllo dough by hand. He’s a marvel, and you appreciate every flaky bite of baklava all the more for what he teaches you. In the heart of her family’s olive groves, our friend Joanna waves you in to wander on the farm and taste their prize oils. On the epic side of the equation, Crete is home to magnificently preserved Knossos where an expert guide tells the tales of King Minos and the Minotaur.

Next is Naxos. There is a countryside walk here that is a fantastic amble in landscapes that have hardly changed for millennia. The island is famous for its 2,500-year-old kouros, a sculpture half-hewn from the marble quarry where it still lies. Did that sculptor wash down the dust with some citron liqueur? It’s a shame if he didn’t. You get your own taste at a small family distillery where they’ve made the bright green brew from the leaves and fruits of citron trees since the 19th century.

One all-new day on this trip is just the kind that I love best. It begins with a ferry ride to Mykonos, the Greek isle to end all Greek isles. Vibey, bustling, and hip, it’s one of those places you just need to say that you’ve seen. But even better, it’s the jumping-off point for Delos. A UNESCO World Heritage Site, Delos was the mythological birthplace of Apollo and Artemis. A private guide waits to take you on an exclusive exploration of what are regarded as the Mediterranean’s most important architectural digs. It’s startling – and absolutely typical – to see the faces of ancient civilization and contemporary culture on a single Aegean day, and it’s the kind of experience that helps you understand the real Greece.

The grand finale of your trip is a jaw-dropping stay in white-washed, blue-roofed Santorini. Throughout this trip, we find ways to avoid touristic Greece and show you the country at its best. That really matters in Santorini where cruise ships sometimes disgorge scads of tourists all at once. Our itinerary spares you that sight. You actually walk into Santorini on a path through vineyards. During your time here, you take a trip on a small boat into the waters of the volcanic caldera. For the trip back to the top, you can take the gondola or (my preference!) ride a donkey as the locals have for thousands of years. At the end of all of your island-hopping days, you find yourself in luxury 5-star hotels, but I have to say that the villa-style hotel here is my absolute favorite. It clings to the town’s steep slopes, guaranteeing you a ringside seat for views beyond compare. Every evening, I settled there with a glass of wine there to watch the sunset, but the show is so gorgeous that I kept forgetting to drink it.

Simply put, this is the best way imaginable to experience the Greek Isles. You get the impossibly blue seas, the rich antiquities, and a variety of island cultures that’s much more diverse than you ever imagined. Layer in the many chances you have to meet local people and be immersed in the lives they live, and I know you will wish your odyssey could last a few years longer!