The Greek Islands Are Calling: Our Favorite Islands and Why We're Going in 2027

There is something about the Greek islands that gets under your skin in the best possible way. The moment you step off the ferry and feel the heat rise up from the cobblestones, smell the sea salt in the air, and hear the sound of a taverna spilling music out onto a sunlit square, something in you just exhales.

Greece has been on travelers' dream lists forever, and for good reason. But the islands are not all the same, and that is exactly what makes them so endlessly interesting. Each one has its own personality, its own rhythm, and its own particular kind of magic.

We are heading to Greece in September 2027, and we would love for you to come with us. But first, let us take you on a little tour of some of our favorite islands so you can start dreaming.

Paros: The Island That Gets Everything Right

Paros sits at the heart of the Cyclades and has a way of making every kind of traveler feel at home. It’s lively enough to keep things interesting, yet relaxed enough to slow down and truly breathe. The island offers golden-sand beaches, the charming old town of Parikia, home to a striking white-marble cathedral dating back to the 4th century, and a thriving food and wine scene that makes lingering over a meal part of the experience.

Naoussa, a picturesque fishing village on the island of Paros, has evolved into one of the Cyclades’ most captivating cosmopolitan enclaves. It’s the kind of place that invites you to linger. Wander its maze of narrow, whitewashed lanes, settle in for freshly grilled fish by the harbor, and watch the fishing boats drift in as the sun slips toward the horizon. For those seeking adventure, Paros’s Golden Beach is renowned for world-class windsurfing and kitesurfing. But the island is equally rewarding when the only thing on your agenda is finding a beautiful spot, settling in, and simply taking it all in.

Santorini: Volcanic Drama and Unforgettable Sunsets

Santorini is the Greece of a million postcards, and it earns every single one of them. Sailing into the enormous crater of its submerged volcano with the cliffs rising above you and the white cube houses stacked against the cobalt blue sky, is a breathtaking first impression—and one of those rare travel moments that stays with you long after you’ve left.

The towns of Oia and Fira offer boutique hotels carved into the cliffs, infinity pools overlooking the caldera, and seafood dinners where the sunset turns the whole world golden. For those who want to go deeper, a guided hike up the island's still-active volcano and a visit to the ancient Minoan ruins at Akrotiri add real historical depth to the experience.

A tip worth knowing: September is one of the best times to visit Santorini. The summer crowds have thinned, the weather is still gorgeous, and the island returns to something closer to its true self.

Mykonos: Glamour, Energy, and Hidden Charm

Mykonos has a reputation as the party capital of the Greek islands, and it delivers on that promise. The legendary beach clubs at Paradise and Super Paradise, and the clifftop mega-club Cavo Paradiso, draw an international crowd that knows how to have a good time.

But Mykonos is so much more than its legendary nightlife. The island’s whitewashed medieval capital, Hora, is a delight to explore, with winding lanes, bougainvillea spilling over doorways, and tiny chapels tucked between stylish boutiques and inviting cafés. Beyond the town, beaches such as Agios Sostis offer a quieter side of the island, with golden sand, crystal-clear water, and a sense of escape. And when you’re ready to venture farther, neighboring Naxos and the ancient sacred island of Delos are both easily reached by ferry, making Mykonos an ideal base for exploring more of the Cyclades.

Naxos: The Soul of the Cyclades

Naxos is the largest of the Cyclades and arguably the most underrated. It is greener and more fertile than its neighbors, with a mountainous interior full of traditional villages, olive groves, and hiking trails that most tourists never reach. The beaches are spectacular, stretching for miles of soft sand along the western coast.

Naxos’s old town, known as Chora, is dominated by a Venetian castle and offers a maze of alleys, local bakeries, and small museums to explore. Just outside the harbor stands the iconic Portara, a massive marble doorway from an unfinished temple to Apollo that dates back to 530 BCE. Standing before it, especially as the sun begins to set, is one of those travel moments that makes you pause and appreciate just how ancient, layered, and extraordinary this corner of Greece truly is.

Naxos also produces exceptional local products including cheese, potatoes, and citron liqueur, making it a wonderful destination for food lovers who want to taste the real character of an island.

Crete: The Island That Has Everything

Crete is Greece in miniature. The largest of the Greek islands, it has dramatic mountain gorges, ancient Minoan ruins, golden beaches, and harbor towns that rank among the most charming in the Mediterranean.

The Palace of Knossos, the grand capital of Minoan Crete, is a must. The walk through the wild Samaria Gorge is one of those experiences that stays with you. The Venetian harbor in Hania is perfect for long lunches and slow afternoons. And the beaches, from the rose-hued sands of Elafonisi to the palm-fringed bay at Vaï, are extraordinary.

Crete rewards those who take their time and explore beyond the coastline.

Rhodes: Where History Meets the Sea

Rhodes has been drawing travelers for millennia—and it hasn’t run out of reasons to keep them coming. The medieval walled city of Rhodes Town is a UNESCO World Heritage Site and one of the most fascinating places to walk in all of Greece. The Knights' Quarter, the Palace of the Grand Master, and the old cobblestone streets take you through layers of Byzantine, Ottoman, and medieval history in a way that feels completely alive.

Down the coast, the village of Lindos is a vision of whitewashed houses tumbling toward a turquoise bay, with an acropolis above that looks out over the Aegean sea. Rhodes is a place where every turn reveals something worth stopping for.

Kefallonia: Rugged Romance at Its Best

Kefallonia is the largest of the Ionian Islands and one of the most genuinely breathtaking. The road down to Myrtos Beach is one of the most dramatic drives in Greece, ending at a cliff-wrapped bay with near-luminous blue water. The Venetian harbor of Fiskardo in the north is postcard-perfect and wonderfully unspoiled.

This is an island for travelers who want natural beauty without the crowds, and who love the feeling of discovering somewhere that has not been overrun. It is romantic, unhurried, and quietly magnificent.

Alonissos: Underwater Wonders and Quiet Days

Alonissos is a Northern Sporades island that moves to its own gentle rhythm. There are no packed beach clubs or cruise ships here, just pine-covered hills, turquoise bays, and the largest marine park in Europe. The National Marine Park is home to dolphins, sea turtles, and the rare Mediterranean monk seal.

For travelers who love the water, the Peristera Underwater Museum offers a remarkable experience: diving down to a Classical-era shipwreck in crystal-clear waters. Above the surface, the whitewashed old capital of Hora is quiet and charming, exactly the kind of place you discover and feel lucky to have found.

Now, About That Greece Trip

We are hosting a group trip to Greece in September 2027, and the timing is intentional. September in Greece means warm days, calm seas, fewer crowds, and that golden autumn light that photographers dream about. It is simply one of the finest times to experience these islands.

Our Greece trip includes both a land portion and a sea portion, so travelers can choose to join one or both. We are still finalizing the full itinerary, but if Greece has been calling your name, this is your sign to raise your hand early.

Interest list spots go first, and we would love to have you with us.

Add your name to the Greece 2027 interest list at toastabletravel.com/greece-2027 and we will be in touch with all the details as they come together. Because some trips are too good to wait on.

Source: Walker, Kerry. "The 12 Best Greek Islands." Lonely Planet, July 30, 2026.

Greek Islands