“It takes a lifetime to discover Greece, but it only takes an instant to fall in love with her,” the famed US author and artist Henry Miller once said, and boy was he right.
With an estimated 1,200-6,000 islands it could actually take several lifetimes to truly discover Greece, but you can still experience the glory of the Hellenic Republic, which is often referred to as the “cradle of Western civilization” in a paltry two weeks.
So, the question is, where to start? Well, luckily we’re here to help you plan your perfect big fat Greek getaway.
Start at the heart
Athens is both the modern-day capital and the heart of Ancient Greece. The country’s largest city is one of the world’s oldest, with a recorded history spanning 3,400 years and a human population dating back to somewhere between the 11th and 7th millennium BC. Now, that’s OLD.
Not surprisingly, Athens is home to a slew of classical architecture, including its iconic Acropolis, an ancient citadel built sometime in the 5th century on a craggy, walled hill, as a home for Athena, the patron goddess of the city.
The Acropolis incorporates several ancient buildings, including the Parthenon, The Propylaia, The Temple of Athena Nike and The Old Temple, in addition to two museums housing sculptures, jewelry, vases, statues and other antiquities that weren’t looted and stolen by the Turks and Brits over the centuries.
Athens is a city of extreme contrasts: stunning beauty and outright ugliness; the modern and the ancient; the sea and the mountains. It’s noisy, crowded, polluted, and since the financial crisis of 2008, it’s been victim to an array of social and economic issues, and decay.
That said, there are more than enough archaeological sites, restaurants, bars, shops and museums to keep you occupied for a couple of days, and it’s a great starting point to launch your island hopping vacay.
Around 200 of the Greek Islands are inhabited, and each of them has its own unique vibe, there’s literally an island for whatever floats your boat, and with an amazing ferry system in place it’s easy to jump from one to another.
Here’s a brief guide to our favorite islands to help you plan your pick.
Get your party on
Mykonos is a 24-hour party island, it’s like Ibiza’s Greek sister, and in addition to its vibrant and pulsing nightlife, it’s also one of the world’s most LGBTQ-friendly holiday destinations.
Mykonos has been a bohemian beach bum favorite since the 1960s, but over the years it’s turned from hippie hotspot to supermodel and superyacht playground. You can get your glam on with fabulous drag queens and oiled-up bodybuilders in super hip beach bars and clubs; stay in the hottest new hotels; dine-in fabulous five-star restaurants, and watch the spectacular sunset over Super Paradise bay.
If all the glitz and glamor gets too much for you, then you can visit the charming traditional old town, or take a breather by cruising to the tiny island of Delos, an archaeological sanctuary with a temple dedicated to Apollo, the Greek god of light.
Skopelos achieved cinematic fame when it was used as the backdrop for the 2008 rom-com Mama Mia, but it’s been a popular holiday destination for families and couples for decades.
Located between Skiathos and Alonissos, Skopelos’ picture-perfect scenery and breathtaking views of the Aegean Sea make it Instagram perfect, complete with traditional old villages such as Town and Glossa perched on top of hills.
Life on Skopelos is decidedly chill, with snorkeling and scuba diving in the crystal clear ocean; lazing in the sunshine and dining in one of the many little local tavernas making up the main ways to while away the hours.
In addition to being Greece’s top tourist spot, Santorini is the number one pick for couples and honeymooners alike–it’s romance central, as well as jaw-droppingly beautiful.
The island has some of the most dramatic ocean views in the world, in addition to psychedelically colored cliffs; natural hot springs; a flooded volcanic crater; narrow cobblestoned streets with perfect whitewashed cave-like houses and windmills; blue-domed churches and a variety of amazing little boutique hotels and shops.
Santorini even has an ancient city, called Akrotini, which was perfectly preserved under layers of ash after the Island’s volcano exploded 3,500 years ago, also causing its distinct and unique white, red and black sand beaches.
Located in the heart of the Ionian sea, and accessible from the mainland by car via a small bridge, Lefkada is the go-to Island for surfers and watersports enthusiasts.
Lefkada is one of the most breathtaking of the Greek islands and with its stunning golden beaches, mesmerizing turquoise waters and wild, natural landscapes it’s easy to understand how it earned the nickname of the “Caribbean of Greece”.
Watersports are the name of the game on Lefkada, with scuba diving, kitesurfing, windsurfing, paragliding, snorkeling and surfing opportunities a-plenty, but it’s also a great pick for any sailing lovers with the opportunity to charter boats and sail around the surrounding islets.
Go big or go home
Crete is the largest of the Greek islands, and Rhodes is the fourth (behind Euboea and Lesbos).
Although the islands have their own unique charms, both offer picturesque villages, buzzing towns, vibrant nightlife opportunities, stunning golden beaches and plenty of tourism options.
Crete is a stone’s throw from Spinalonga, a beautiful Islet that was transformed into a leper colony from 1903-1957, where anybody in the region afflicted with the disease was stripped of their assets and banished to, without any medical care or assistance. At its peak, Spinalonga was home to 400 lepers, and its last inhabitant, a priest, didn’t leave until 1962. The Greek government attempted to hush up the sad history of Spinalonga for decades, but these days it’s possible to tour the island with a number of boats sailing there daily.
Rhodes is home to an amazing ancient Acropolis perched on top of a 380-foot high rock with historic walls, battlements, a Hellenistic stoa, and a temple dedicated to Athena Lindia. Not surprisingly, you can enjoy absolutely breathtaking views of the surrounding ocean and island while there, in addition to taking a fascinating step back in history.
The two islands are also home to international airports, allowing the option to fly there directly.
Corfu is the most cosmopolitan and multicultural of the Greek islands, having been strongly influenced by the English, Venetian and French colonialists over the centuries.
With its lush green hills; expansive sandy beaches; charming squares; pastel villages; luxurious resorts; rolling olive groves; amazing architecture; wild natural landscapes; fascinating museums, and pulsing nightlife, it’s also one of the “most likely to please” islands, with something for every traveler, from singles, to couples, to families.
The Island varies from region to region, with the North-East side favored by the jet-set and glitterati, and the center and old town a haven for culture-vultures and foodies.
Unless you like to drink your beer by the bucket followed by endless Jägerbombs, all whilst enjoying a wet T-shirt contest, you’d do best to give the south of Corfu a wide berth though, especially Kavos, every football hooligan’s favorite haunt.