Even though the mountainous area of Sfakia was very difficult to approach, it had been strongly connected with the history and civilization of the first-Minoan period (3500 2025 BC), especially the cities of Anopolis, Aradena and Askifou.
Prehistoric residents seem to have preferred the coastline (Tarra, Phoenix, Pikilassos).
Since the end of the Neolithic period there has been evidence of ancient habitation on Madares, near some mitata (small buildings where the shepherds used to rest and produce their delicious cheese).
During the Hellenistic and Classical period the people of Sfakia got away from the coast and built strong walls to protect themselves from the enemies. This was probably due to an increase in piracy and the political insecurity due to the war in the area.
During the Roman domination, coastal cities gradually started existing again, till the end of this period when there were much more.
Phoenix. An ancient city and the harbour of Anopolis and Aradena, near today's Loutro. There are remains from all historical periods as well as underground domes.
Loutro. An ancient city that owes its name to the existence of bathtubs with water channeling from Anopolis. Their remains are still there.
Aradena. It is the ancient city of Aradin or Iradin which was probably found by the Phoenicians. It was an autonomous city with its own currency. Its architectural remains and tombs still stand there among the ruins of the village.
Anopolis. The ruins of the ancient town are near today's village of Anopolis. It was an autonomous city with its own currency and it flourished mainly during the Roman and the Byzantine domination.
Tarra. An ancient coastal city built right after the exit of Samaria gorge, where today lies Agia Roumeli. It was a small but powerful city with its own currency. The coins represented the Cretan wild goat on the one side and a bee on the other. It is believed that in the wider area they made glass because in an excavation in 1959, they found tombs of the Archaic period, 5th 4th century BC, full of funeral gifts. A well fortified city that had been constantly inhabited from the Classical period till the Roman domination.
Pikilasion or Pikilassos. An ancient town between Suia (Sougia) and Tarra (Agia Roumeli) in Tripiti Gorge of Sfakia, at today's Boukelasi, built at and altitude of 400m. It was probably the harbour of Eliros. The city existed during the Archaic, the Classical and the Hellenistic periods. It was abandoned during the Roman domination and the settlement was later established in the exit of Tripiti gorge. The remains of two temples have been found along the coast.
Kaino. A small mountainous ancient city, built inside Samaria gorge near the banks of the river. The city developed in the ancient years and according to tradition it was the birthplace of Artemis the Britomartis, called Diktini, who was the daughter of Zeus. In 1991, they found an outdoor sanctuary near the church of Agios Nikolaos as well as many bronze and iron, arrows and spears. That was probably the oracle of Apollo or else, the Kirikion Andron. It is said that the nymph Akakali, wife of Hermes and daughter of Minos was worshipped there. (Hermes used to hold a cane called “Kirikion”).