Ready for Greece? Where to First?

With more than 200 inhabited islands for a lifetime of summer escapes, it’s hard to know where to start with Greece. If you’ve only heard of an island in Greece, it’s likely to be Santorini or Mykonos. I would avoid Mykonos entirely, for reasons explained here. Santorini truly is a bit of magic, but only if you’re visiting in early Spring or late Autumn.

I will also venture to say that I don’t think cruise ships with day-long stopovers are the best way to enjoy its islands. Nor are all-inclusive resorts designed to keep you hotel-bound. Greece is for exploring. And loving Greece, without some luxe city comforts and with its idiosyncratic ways, can be a gradual process. But once you cast-off certain seasoned traveller expectations and allow its multifaceted character to unfold, it’s hard not to love deeply.

Time is required. It would be remiss to sweep through Greece in 3 to 5 days. Also depending on where you are travelling from, and how long you take to get over jet lag, allow for at least 8 to 14 days on a large island like Crete, or on 2 or so small-ish islands within an island group. Unless you’re trying to satiate a voracious travel appetite, or have lots of time, we wouldn’t pack too many islands into a trip.

Ready to start? Here’s how:

PICK AN ISLAND GROUP

Geographically clustered and usually well-connected by ferries with near neighbours, Greece’s 6 island groups include:

• The Cyclades – This region of blue and white sugar-cube jewels set in bare rock surroundings are the country’s most popular island group. Islands with airports include Santorini, Mykonos, Milos, Paros, Naxos, and Syros.
• The Saronic Islands – The closest island group to Athens (and all without airports), these include Aegina, Spetses and Hydra.
• Ionian Islands – Famous for fantastic beaches, stunning landscapes and incredible swims in Zakynthos and Lefkada. Also of Corfu fame. Most islands here have airports.
• The Sporades – Lush and leafy, these evergreen islands include those of Mama Mia! fame like Skiathos and Skopelos. Skiathos and Skyros has an airport.
• Dodecanese Islands – Rhodos, Kos and Patmos are perhaps the most well-known here. Far-flung and requiring long ferry journeys, most visitors fly into these islands.
• The Northeast Aegean Islands – A scattering of islands in the northeast that lie outside the other island groups.

I strongly suggest the Cyclades for first-timers. While Greece brims over with beauty, the charm of Cycladic village architecture is original. Well-connected to a diverse array of neighbours by high-speed ferries, this group also lends itself well to easy island hopping. The island pairs suggested below are our personal favourites.

CYCLADIC ISLAND-HOPPING ITINERARIES

After flying into the first destination (all first destinations listed below have airports), high-speed ferry travel times to the second destination are highlighted below:

1. Santorini <> Naxos (1 hour 5 minutes)
2. Santorini <> Milos (2 hours)
3. Naxos <> Koufonisia (40 minutes) 
4. Milos <> Naxos (2 hours 20 minutes)
5. Milos <> Sifnos (50 minutes)
6. Paros<> Sifnos(55 minutes)

You can add day trips to some island pairings e.g. while on Milos, sail or ferry over to Polyaigos and Kimolos.

IONIAN ISLAND-HOPPING ITINERARIES

Striking good looks don’t stop with the Cyclades. The Ionian islands display drama and distinct personalities of their own. This would be our second island group of choice after the Cyclades. You can start by flying into Corfu, Kefalonia or Zakynthos, and continuing with your inter-island explorations by ferry.

ONE-STOP DESTINATIONS & ROAD TRIPS

If car travel sounds more appealing than braving the sea, fly into the first destination listed below and continue with a road trip:

1. Crete: In its expanse, you won’t get bored even for 2 weeks on the island. Combine Crete (departing from Heraklion) with Santorini (1 hour 50 minutes via high-speed ferry) and other Cycladic destinations if you like.
2. Athens > Messinia, Peloponnese (3 hours and 30 minutes by car). Enjoy luxe hotels? An opulent string of properties (Mandarin Oriental, W Hotel and The Westin) have sprung up on Costa Navarino just 15 minutes from impressive Voidokilia beach nearby. Stop by ancient Mycenae of King Agamemnon fame on the way.
3. Thessaloniki > Halkidiki (1 hour 30 minutes by car), with some of the best beaches in the Mediterranean.
4. Athens > Lefkada (4 hours and 15 minute by car). There are just two islands connected to the mainland by land – Lefkada and Evia. Lefkada’s beaches are far more impressive. Make a stop at Corinth Canal en route.