Iraklia is the westernmost of the Small Cyclades, the chain of little islands that lies between Naxos and Amorgos, and the smallest of them by area. Fewer than 200 people live there year-round. There is no big resort, no airport and very little traffic, which is exactly why people make the long journey from Athens to reach it.
The direct ferry from Piraeus is the simplest way to get there with luggage, because it removes the need to change boats at Naxos. You board in Athens' main port and step off in Agios Georgios, the island's harbour, which is also its main village. It is a day at sea rather than a quick hop, so treat the crossing as part of the trip and plan a relaxed first evening.
Two operators appear on this route in our data. Blue Star Ferries runs the big conventional ships that carry cars and serve the Small Cyclades from Piraeus, and Seajets adds faster sailings in the warmer months. The trade-off is simple: the conventional ship takes longer but has open decks, space and room for vehicles, while the high-speed boat saves hours at a higher price.
Because departures are not daily all year, build your trip around the boat rather than the other way round. Pick your sailing first, then book your room, and allow a spare day before any flight home. Iraklia also works well as the first stop on a hop through Schinoussa, Koufonisia and Naxos.