Sea & sailing
Greece has around 13,700 kilometres of coastline and six thousand islands and islets, of which some two hundred are inhabited. A great deal of the best of it has no road.
About Sea & sailing
The distinction worth making is between a boat as transport and a boat as the trip. A day caïque with a skipper unlocks coves, sea caves and tavernas with no land access, and returns you to a hotel bed each night. A chartered yacht with crew makes the sea itself the destination — a different holiday, and one that rewards a week rather than three days.
Where you sail changes everything. The Ionian is sheltered, short-hop and forgiving, which makes it the family and first-timer water. The Cyclades are open, deep and windy — exhilarating, and in July and August subject to the meltemi, which can pin you in harbour. The Saronic is easy and close to Athens. The Sporades have a marine park.
For non-sailors, the underrated option is the skippered day boat repeated three or four times across a week from a single base. It gets you the same water with none of the logistics.
Where it is at its best
Kleftiko by sea
Milos
Sea caves and white rock arches with no land approach at all.
The Ionian short hops
Paxos, Antipaxos, Meganisi
An hour between anchorages, sheltered water, and no swell to speak of.
The marine park
Alonnisos
Europe's largest protected sea area, monk seals, and uninhabited islets.
The Athos coast
Halkidiki
A thousand years of monasteries, seen only from the water.
Regions for this

Cyclades (classic)
Santorini, Mykonos, Paros, Naxos. Famous for good reason, and entirely manageable if you get the hours right.
Cyclades (off-grid)
Milos, Folegandros, Sifnos, Amorgos, Serifos, Kimolos. Same light, same sea, a fraction of the people.
Ionian (Eptanese)
Corfu, Kefalonia, Lefkada, Zakynthos, Ithaca, Paxos. Green, Venetian, and the closest Greek islands to Malta.

Dodecanese
Rhodes, Symi, Patmos, Karpathos, Nisyros. Medieval, Italian, monastic — the Aegean's most layered islands.
Sporades
Skiathos, Skopelos, Alonnisos, Skyros. Pine forest to the waterline and Europe's largest marine park.
Pelion & Magnesia
The mountain of the centaurs: chestnut forest running down to two different seas, and skiing above a beach.

Halkidiki & Thessaloniki
Three peninsulas of pine and clear water, and the best eating city in Greece behind them.