A Local’s Island-Hopping Guide: The Cyclades and Beyond

 

When I tell people about Greece, I often say that the sea here is not just a view. It is a companion — a constant presence at every meal, in every village square, on every ferry crossing. And nowhere is that more true than on the islands. Not only the famous ones you see in photographs, but also the quiet, unassuming ones you reach with a little sea salt in your hair and a soft smile you didn’t know you had.

I wasn’t born in Greece, but I fell in love with her at nineteen. I remember weekend ferry rides from the mainland, walking barefoot on warm sand, and eating fish that had been pulled from the sea only hours earlier. Three years later, I moved there and spent the next two decades living permanently in Greece and the past 15 years visiting as often and long as possible. Its rhythms are now my rhythms. I know many of its hidden paths, its coves, and seek out new ones with every visit.  The beauty of eating at tavernas that open not just to feed travelers, but because feeding people is part of who they are. My passion for Greece and Greeks shaped what I do today: offering EVGE, the extra virgin olive oil brand rooted in honesty and heritage, and creating Be My Guest in Greece, where I help travelers experience this country the way Greeks do — slowly, warmly, and with intention.

Choosing the Right Islands

Travelers often tell me they feel pressure to choose the “best” islands for a short trip. After thirty-five years of traveling through Greece and visiting forty-six islands (so far), I can tell you with certainty that there is no single “best” island. There are only islands that are best for you — whether you love beaches or villages, hiking or food, nightlife or quiet coves, whitewashed towns or dramatic landscapes.

Most island-hopping begins from Athens, with ferries leaving Piraeus or Rafina for the Cyclades. Santorini and Mykonos are the famous names, but the Cyclades also include Paros, Naxos, Milos, Amorgos, Koufonissi, Folegandros, Serifos, Sifnos, Anafi, Donoussa, and so many others. Beyond them are the Ionians, the Dodecanese, the Sporades, the Northern Aegean Islands, the Saronics, Evia, and Crete — almost a country unto itself.

For travelers wanting a lively-and-quiet combination, I often pair Paros with Milos. For those wanting balance between vibrant landscapes and soulful simplicity, I recommend Naxos with Koufonissi or Naxos with Amorgos. Each pairing has its own charm and its own pace.

Mykonos

Mykonos has an international reputation: whitewashed houses glowing in Cycladic light, iconic windmills, a harbor full of yachts, and a nightlife that wakes just as other cities are going to sleep. Yet if you only stay one night, you miss the deeper layers of the island.

I prefer arriving in the late afternoon, settling into a seaside café, and watching the sun shift across the windmill hill. As evening approaches, I wander through Chora’s winding alleys, where the light softens and the shops begin to glow. Dinner is best away from the crowds of Little Venice — somewhere quieter, where the food is simple and fresh.

The next morning I like to escape to Ano Mera, an inland village with a peaceful square and a monastery courtyard that feels timeless. Afterward, I head toward a northern beach like Kalafatis for a swim and a relaxed meal by the sea. Mykonos at dusk has its own magic — a rising hum, a feeling of anticipation. And for those drawn to history, an early-morning boat to Delos is unforgettable. Arriving before the crowds feels almost sacred.

Paros and Milos

Paros is lively and stylish without overwhelming you. Naoussa is the island’s crown jewel — a harbor lined with whitewashed alleyways, lively cafés, and tavernas that glow in the evenings. Days move gently here, from beach dips at Kolymbithres to wandering the village streets at dusk. For travelers seeking something quieter, Piso Livadi offers a slower pace and charming seaside dining.

Paros pairs beautifully with Milos, a volcanic island known for its extraordinary natural forms and colorful landscapes. The cliffs, coves, and beaches look as though they’ve been sculpted by hand. Fishing villages like Klima, where boats rest inside carved boathouses, remain among the most picturesque in Greece. Combining Paros’s polished charm with Milos’s raw beauty makes for a wonderful, balanced trip.

Naxos With Koufonissi or Amorgos

Naxos is generous in every way — large, green, deeply traditional, and filled with some of the best food in the Cyclades. Long sandy beaches stretch toward the southwest, while inland villages rise into the mountains. I love spending at least one night inland in villages such as Apeiranthos or Melanes, where marble pathways climb toward the hills and goats wander through stone alleys as though time has paused.

Food on Naxos is exceptional. Stuffed zucchini flowers, lamb moussaka, sun-ripened tomatoes, local cheeses, fragrant honey — everything tastes connected to the land. While Naxos isn’t a major olive-oil-producing island, tavernas use beautiful oils from Crete and the Greek mainland, and the meals feel deeply rooted in tradition.

Naxos pairs naturally with Koufonissi, a tiny island that feels like a secret. Sandy footpaths, crystalline coves, and water so clear it looks illuminated from below make it one of the most relaxing places in Greece.

For travelers wanting something more dramatic, Naxos and Amorgos is an unforgettable combination. Amorgos is wild and soulful, full of cliffs that plunge into the sea, remote walking paths, and whitewashed villages perched against the sky. The monastery of Hozoviotissa, clinging impossibly to the cliffside, is an experience that never leaves you.

Crete

Crete is not simply the largest Greek island — it is a world of its own. Mountains rise into the clouds, gorges cut through ancient rock, beaches glow with white or pink sand, and Minoan palaces lie scattered across the landscape. Culture, complexity, and warmth define everything here.

My relationship with Crete began in 1987, during a week that changed my life. The star-filled skies, the warmth of the people, and the depth of its culture inspired me to study Greek and devote myself to this land. Today, Crete remains close to my heart — especially since my son is now studying medicine at the University of Crete in Heraklion.

Crete deserves at least five nights, though longer is even better. Chania is enchanting with its Venetian harbor and access to some of Greece’s most stunning beaches. Rethymno blends charm with convenience and offers an easy base for visiting Minoan archaeological sites. Heraklion is perfect for history lovers, home to the Archaeological Museum and the ancient palace of Knossos. In the east, Agios Nikolaos and Elounda offer elegant seaside stays and a quiet sense of luxury. 

Food in Crete is philosophy. Meals often begin with raki, followed by snails in wine sauce, wild greens, fresh fish, fava, and slow-cooked lamb. Crete’s olive oil — bold, golden, and deeply fragrant — is at the heart of everything.

Getting Around and Moving at the Right Pace

Ferry travel is one of the best parts of island-hopping. I like to book the first legs in advance and leave room for spontaneity later on. Sometimes the best experiences come from taking a smaller boat to a lesser-known port, simply because the timing feels right. Choosing an island like Paros or Naxos as a home base makes exploring nearby islands easy without constant packing and unpacking. I always recommend giving yourself at least one morning with no plans at all — letting the sea decide.

Living Like a Local: Food, Taverns, and Hospitality

Traveling like a local means seeking out the tavernas where islanders eat. One night on Naxos, I found a small family taverna where the owner began singing old songs with his guitar. He brought us dessert “because you stayed long enough,” and in that moment, the meaning of Greek hospitality came alive once again.

Food is never just food in Greece. Olive oil, bread, wine, vegetables from small gardens — everything carries a story. The connections I formed with farmers and producers over the years shaped my desire to bring Greek olive oil to American families through EVGE, connecting kitchens across continents.

Why Travel With Someone Who Knows the Islands

You can absolutely travel on your own and have a beautiful experience. But traveling with someone who has lived on the islands, walked their docks in every season, tasted oil at harvest, discovered hidden beaches, and understands how to match travelers with the right islands creates a different kind of journey.

Through Be My Guest in Greece, I design trips that follow local rhythms, avoid unnecessary stress, and prioritize authentic, soulful experiences. Thoughtful guesthouses, realistic ferry schedules, balanced pacing, and meaningful local encounters all shape the trips I create.

Final Thoughts on Island Life

At the end of an island-hopping journey, something inside you changes. The sea becomes familiar. The bakery you visited once stays in your memory. And the olive oil you drizzle back home tastes like sun and soil.

Travel is not just about seeing new places — it is about letting those places see you.
In Greece, you are never just a visitor — you are a guest. And if you explore the islands with that understanding, whether you find yourself wandering Mykonos at dusk, swimming in Koufonissi’s glowing waters, savoring tomatoes in Naxos, or exploring Crete’s wild landscapes, you will return home not with souvenirs, but with memories rooted in real people, real places, and real food.