An Island-Hopper’s Guide to the Most Enchanting Greek Isles
“Happy is the man, I thought, who, before dying, has the good fortune to sail the Aegean sea,” writes Nikos Kazantzakis in Zorba the Greek.
Once the heart of Western civilisation, Greece birthed some of our greatest early thinkers from Plato to Aristotle, and left such an epic mark on the world that even today, we’re still using the Greek alphabet in mathematics and science. And who could forget the mythology of the land? One that is so widespread and legendary that it rivals no other.
Practically every city and island within the Aegean and Ionian Seas contains a mystical story, whether of heroic originations or monstrous geneses. With a staggering upwards of 6,000 offshore islands and islets in the archipelago (inhabited and uninhabited alike), get a taste of walking through history’s most intriguing hallways, while sipping on a piña colada and getting a wicked tan on top of a speedboat. Here’s a primer to the Greek islands no vacationer should miss.
Like how Athens is the go-to city for newcomers to Greece, Santorini is typically the first stop for island-hoppers to ease into the Greek archipelago experience. Perched on a volcano, the crescent-shaped isle is most known for its idyllic architecture, specifically, those iconic white buildings with bright azure domes.
Overlooking the Aegean Sea, it’s a popular honeymoon spot that offers narrow, sloped alleys—a charming departure from the level streets of regular cities. Another awe-inspiring feature of this island is its black-sand beaches, created by thousands of years ago by volcanic eruptions. They offer a darker, more mystical backdrop to the romantic scenery, an unexpected sight in such a pristine destination.
Legend has it that Hercules, after slaughtering a bunch of giants, dumped them in a pile at the heart of Cyclades, which petrified over time to form Mykonos, the island of the winds. While rooted in the mythology of Greece, its current reputation supersedes its rich history. Today, it stands as the destination, where thrill-seekers congregate. Here, the rave culture is what defines this island’s identity, rivalling that of Ibiza.
Besides adrenaline-pumping water sports such as windsurfing, sea parachuting and jet skiing, it also serves the upper echelon of travellers with luxury hotels and lavish blowouts. Don’t be surprised to catch a celebrity sighting of Keith Richards or a Victoria’s Secret supermodel flouncing around in her bikini.
This island boasts a melting pot of cultural influences that blends the French, British and Italian. It features enchanting Venetian fortresses and medieval castles, a Paris-inspired Liston Street in the Old Town (a UNESCO World Heritage site) and decadent neoclassical villas that attract the attention of the rich and famous.
To satiate the epicureans, the Agni bay offers unparalleled gourmet treats, some of which have received a stamp of approval from the likes of George Osborne and Peter Mandelson. Besides the island’s characterful inhabitants and architecture, Corfu Island also shines as a lush, evergreen spot for nature lovers to take in the marvels of Mother Nature.
Hydra is an uncommonly curated island that follows a strict and singular aesthetic—traditional vintage. In an effort to preserve its heritage and quaint landscape dotted with historic landmarks, it has banned the construction of modern infrastructure and even the use of neon signs.
The locals here don’t travel by cars or motorcycles either. Rather, they get around on old-school bicycles and donkeys, an even more antiquated mode of transportation. Yet, that’s exactly what makes Hydra, a place where time stands still, so irresistible. The late Leonard Cohen, who once lived here, would agree. As would the throngs of artists and art collectors who have made this island a creative hub, brimming with gallery spaces, museums and exhibitions.
Beyond its off-limits beaches that protect endangered loggerhead turtles, Zakynthos Island, or Zante, is chock-full of rugged coves and cliffs, and animal sanctuaries nestled within the mountainous regions of the isle. One of the most family-friendly pit stops in the Greek archipelago, this Ionian Sea gem covers itself with dense pine forests (amidst sleepy hamlets) that lead into the sapphire ocean.
Among its multiple beaches, the one that should top your list is the Shipwreck Beach, which is also known as Smugglers Cove or Navagio Beach. Hop on a ferry to reach its pristine shores, made famous by a shipwrecked vessel that has been sitting along the coast since 1980.
While it’s beach-lounging season all year round on the largest island in Greece, this getaway is also home to snow-capped mountains—offering a visual symphony of the glaciers. Venture inland to explore the ancient ruins of the Minoan palaces and towns, religious sites that date back to the 14th century, and a smattering of modest yoga retreats.
For a more active itinerary, head for the Samaria Gorge, which spans 16km, with a few abandoned settlements and a whole lot of Instagrammable glory—from creeks to wild goats. Steer clear of the north-east and journey south instead if you’re looking for a quiet, under-the-radar escape, an antidote to tourist-infested, serenity-deprived spots.