Heraklion

This is the part that decides most trips. From Heraklion you can sail on to the islands:

• Santorini — 4 sailings, about 2 hours, on Blue Star, Minoan Lines and SeaJets.
• Milos — 5 sailings, roughly 4 h 20 m.
• Naxos, Anafi and Syros — single sailings, but they exist.

From Chania, none of these do. Combining Crete with the Cyclades in one trip means arriving or leaving through Heraklion.

Heraklion to Piraeus takes about 9 h 15 m with 5 sailings in our timetable. The ships leave at 21:00 and dock around six or seven in the morning — a night's sleep that also happens to be the journey.

At the Athens end, Crete ferries use gates E2 and E3 at Piraeus. That is worth writing down: Piraeus is enormous, the gates are far apart, and the taxi rank does not know which one you want unless you say.

On a nine-hour overnight the difference between a cabin and an airline-style seat is the difference between arriving rested and arriving wrecked at 06:00 with a full day of Crete ahead of you.

The economics usually work out anyway: a cabin replaces a hotel night at both ends of the trip. Book it early in July and August, when the Cretan routes carry as much resident and freight traffic as tourist traffic.

Knossos is fifteen minutes from the port, and the Archaeological Museum in the city holds the finds from it — the two belong together and most people see only one. Beyond that, Heraklion is the base for central and eastern Crete: the Lasithi plateau, Malia, Agios Nikolaos, and eventually Sitia at the far end.

The city itself gets skipped by visitors in a hurry to leave it, which is a fair judgement about the outskirts and an unfair one about the old harbour and the Venetian walls.

All the Piraeus ships are car ferries and Heraklion is the more straightforward Cretan port for driving off: the road network out of the city is direct in three directions, and the east of the island is only sensibly reachable from here.

If you are shipping a vehicle unaccompanied rather than driving it aboard, Heraklion is also the Cretan port that handles it — Chania does not.

A common and good itinerary: fly into Chania, work east, and sail out of Heraklion to Santorini. It avoids backtracking, uses each port for what it is best at, and turns the 150 km between them into the trip rather than a chore.

The reverse works equally well. What does not work is booking both legs through the same port because it was simpler at the time.

The Piraeus overnights run year round — they are Crete's supply line, not a seasonal service. The Cyclades links are the seasonal part, thickening from May and thinning after September, with Santorini holding on longest.

Late September is the best window here: the sea crossings are all still running, the museum and Knossos are bearable, and the island is no longer at capacity.