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.
At anchor 
Afternoon breeze - Image slotKleftiko by sea, Milos. Sea caves and white rock arches with no land approach at all.
- Image slotThe Ionian short hops, Paxos, Antipaxos, Meganisi. An hour between anchorages, sheltered water, and no swell to speak of.
- Image slotThe marine park, Alonnisos. Europe's largest protected sea area, monk seals, and uninhabited islets.
- Image slotThe Athos coast, Halkidiki. A thousand years of monasteries, seen only from the water.
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.
Three ways this trip is shaped
Worked examples, not products. Nothing here is booked or sold — they are simply how a trip of this kind fits together when the distances are respected.
7 days · May – October
The Saronic circuit
- Athens
- Aegina
- Poros
- Hydra
- Spetses
Short legs, sheltered water and a harbour town every evening.
9 days · May – early October
Ionian under sail
- Lefkada
- Meganisi
- Ithaca
- Kefalonia
- Paxos
Reliable afternoon breeze, no meltemi, and anchorages within two hours of each other.
8 days · June – September
Dodecanese by motor yacht
- Rhodes
- Symi
- Tilos
- Nisyros
- Kos
Medieval harbours, a live volcano crater and crossings short enough to swim twice a day.
Regions for this
Santorini, before the ships 
Naxos Chora - Image slotThe caldera by boat, not by road — Cyclades (classic). A private caïque out to the volcanic islets and the hot springs, leaving mid-afternoon and back for sunset on the water.
- Image slotAssyrtiko in the vineyard — Cyclades (classic). Basket-trained vines lying flat in volcanic ash, tasted in a cellar with the person who made it.
- Image slotDelos — Cyclades (classic). An entire uninhabited sacred island, thirty minutes off Mykonos. The most complete ancient city you can walk through in Greece.
- Image slotInland Naxos — Cyclades (classic). Marble villages, a Venetian tower, an emery mine, a kouros lying unfinished in a field where it cracked.
Cyclades (classic)
Santorini, Mykonos, Paros, Naxos. Famous for good reason, and entirely manageable if you get the hours right.
Sarakiniko, Milos 
The Sifnos paths - Image slotMilos by boat, all day — Cyclades (off-grid). Kleftiko's sea caves, Sykia's collapsed roof, and coves with no land access at all.
- Image slotThe Sifnos footpath network — Cyclades (off-grid). Two hundred kilometres of waymarked old paths between villages, monasteries and bays.
- Image slotPanagia Hozoviotissa, Amorgos — Cyclades (off-grid). A white monastery pinned to a vertical cliff three hundred metres above the sea.
- Image slotClay-pot cooking — Cyclades (off-grid). Revithada and mastelo, cooked overnight in a wood oven, eaten on Sunday like everyone else.
- Image slotThe Lion of Kea — Cyclades (off-grid). A smiling archaic lion cut from the rock above Ioulida, reached on foot in twenty minutes.
- Image slotKolona, Kythnos — Cyclades (off-grid). A sandbar with sea on both sides, best swum to from a boat before the afternoon wind.
Cyclades (off-grid)
Milos, Folegandros, Sifnos, Amorgos, Serifos, Kimolos, Kea and Kythnos. Same light, same sea, a fraction of the people.
North-east Corfu 
Off Antipaxos - Image slotA day boat to Antipaxos — Ionian (Eptanese). Two beaches with Caribbean water, twenty minutes off Paxos, empty by six.
- Image slotThe Myrtos road — Ionian (Eptanese). Kefalonia's west coast from above — one of the great European coastal drives.
- Image slotCorfu Town on foot — Ionian (Eptanese). Venetian fortresses, the Liston arcade, and a Sunday philharmonic band that has played since 1840.
- Image slotIthaca, slowly — Ionian (Eptanese). Two harbours, a hill village, and the least developed island in the group.
Ionian (Eptanese)
Corfu, Kefalonia, Lefkada, Zakynthos, Ithaca, Paxos. Green, Venetian, and the closest Greek islands to Malta.
Lindos, first entry 
Symi harbour - Image slotThe Street of the Knights, after six — Dodecanese. Walked when the ships have sailed, with a guide who can join it to Malta's own story.
- Image slotLindos acropolis at opening — Dodecanese. A Doric temple on a rock above two bays, and the village white below it.
- Image slotThe Nisyros caldera — Dodecanese. Walk onto the floor of an active volcano, hissing and sulphurous, then eat in the village above it.
- Image slotOlymbos, Karpathos — Dodecanese. A ridge village that kept its dress, its ovens and a dialect with pre-classical roots.
Dodecanese
Rhodes, Symi, Patmos, Karpathos, Nisyros. Medieval, Italian, monastic — the Aegean's most layered islands.
Koukounaries, Skiathos 
Skopelos - Image slotThe marine park by boat — Sporades. Uninhabited islets, a Byzantine monastery on Kyra Panagia, and a real chance of monk seals.
- Image slotWalking Skopelos — Sporades. Old mule paths between monasteries and plum orchards, in pine shade.
- Image slotSkyros carnival — Sporades. Goat-bell dancers and masked figures in late February — one of the oldest surviving rites in Europe.
Sporades
Skiathos, Skopelos, Alonnisos, Skyros. Pine forest to the waterline and Europe's largest marine park.
East Pelion, October 
Damouchari - Image slotThe Pelion railway — Pelion & Magnesia. A narrow-gauge line designed by Evaristo de Chirico, father of the painter, over stone viaducts.
- Image slotKalderimi walking — Pelion & Magnesia. Tsagarada to Damouchari, downhill through forest, ending at a sea you swim in.
- Image slotSki Agriolefkes, then swim — Pelion & Magnesia. A small ski centre at 1,500 metres, forty minutes from a beach. In February both work.
- Image slotA tsipouradiko in Volos — Pelion & Magnesia. Order by the round; the food arrives on its own logic.
Pelion & Magnesia
The mountain of the centaurs: chestnut forest running down to two different seas, and skiing above a beach.
Thessaloniki, evening 
Sithonia, September - Image slotEating Thessaloniki properly — Halkidiki & Thessaloniki. A morning in the markets, bougatsa, and a long evening of small plates in Ladadika.
- Image slotThe Athos coastline by boat — Halkidiki & Thessaloniki. Twenty monasteries seen from the water, some of them a thousand years old.
- Image slotVergina — Halkidiki & Thessaloniki. Descend into the tomb of Philip II, with the grave goods displayed where they were found.
- Image slotSailing Sithonia — Halkidiki & Thessaloniki. Diaporos and the islets off Vourvourou — shallow, clear, and easy water.
Halkidiki & Thessaloniki
Three peninsulas of pine and clear water, and the best eating city in Greece behind them.