Current suggestions about the antiquity of Chiaramonte Gulfi say that it is located at the site of the ancient town of "Akrillai" - of which more below, but first we look at the history of 'modern' (post-Roman) Chiaramonte Gulfi.
Byzantines, Normans and Angevins in Chiaramonte Gulfi
The Byzantine art is visible in the cave of “Santa Margherita” although the frescoes are largely lost because of moisture; the cave was "dug into an alluvial soil, which has, in part, caused the collapse of it" 
With regard to Norman times at Chiaramonte Gulfi we do not have significant historical data; in fact, F. Maurici notes that:
"the only evidence of the existence of a feudal lordship and the possible presence of a Norman fortress in ancient times is the mention of a knight called 'miles Serlo filius Roberti de Gulfo” [Serlo, son of Robert of Gulfi], as documented in 1120" .
Around 1120 therefore a knight named Robert enfeoffed Gulfi. Among other things, it was in 1120 that the Normans began to introduce the feudal system in Sicily, and this shows that Gulfi "was one of the first fiefdoms of the island" .
The most critical moment for the city was the War of the Vespers, when Chiaramonte Gulfi was besieged and almost destroyed by the Angevins: "It was brutally destroyed by hordes commanded by the Angevin Ruggero Lauria" . The site continued to be inhabited until the early 14th century:
"when these places were totally abandoned, because the people moved to the new town of Chiaramonte Gulfi" .
The founder of the new town was Manfredi I Chiaramonte, Count of Modica and the town in mid-1300 was contained in the County of Modica, which included Modica, Ragusa, Scicli, Santa Croce Camerina, Pozzallo, Ispica and Chiaramonte Gulfi.
The city passed to the Spanish crown until the early 18th century when it entered Austrian domination. It then passed under Bourbon rule until the Unification of Italy in 1861.
Origins and history of ancient Akrillai
With regard to ancient 'Akrilla(i)', it was perhaps a 'chorion' (=small village) of Akrai that has been identified as Akrillai in the archaeological site near the modern Chiaramonte Gulfi - about this there is a brief outline in Stephen of Byzantium (6th century AD) , who used to derive his data from reliable sources, especially from Philistus of Syracuse (432-356 BC), and according to most reliable studies, Akrillai arose from the expansionist aims of Syracuse against the Sikels:
"There can be no doubt that with the foundation of Akrai Syracuse placed a bulwark to defend the coastal plains against the Sikel threats (…) The foundation of Kamarina and Akrillai, presumably founded at the same time or not long after Kamarina, created the conditions for which all the plain east of the Dirillo river were under the control of Syracuse" .
The communications link between the various sub-Syracusan colonies of Akrai, such as Kasmene and Akrillai was insured by a road that led to Selinunte.
In Roman times, after the conquest of the island, the Romans prolonged this road to Lilybaeum. The Roman conquest of Akrillai occurred as part of the servile wars, when the uprising of Euno-Antiochus forced the Roman government to restructure the 'Provincia' of Sicily by separating the various cities that were amalgamated by Syracuse, and thus dangerous for Rome.
The dismemberment of the vast territory of Syracuse took place between 213 and 210 BC, when Acrilla was conquered by Consul Marcellus (196 BC), and the same Akrai, on which Acrilla depended, was made autonomous with the ability to mint its own currency .
In Roman times the small town had a certain economic prosperity and it was undoubtlely an important junction and commercial road. It was mentioned by Plutarch (46-127 AD), Stephen of Byzantium (in "Etnikà"), in which he called it "Akrilla") and Livy [59 BC-17 AD], according to whom the town was situated along the road between Agrigento and Siracusa. B. Peace spoke of:
"[...] (the presence of a large number of Roman burials) grew in Roman times along the main roads crossing the plain, when the site of Kamarina remained almost deserted (...) while according to memorials and the archaeological remains Acrilla, Caucana and Bidi seem real small towns" .
Origins of the name Chiaramonte Gulfi
With regard to the first part of the name, there is no doubt - it derives from the name of its founder, Manfred I Chiaramonte (died 1391), who in the early 14th century founded a new town not far from the older site of Gulfi. More problematic is identifying the meaning of "Gulfi". The most reliable studies attest that it is of Arab origin:
"Given its location, it is very likely that the first contacts of Akrillai with the Arab occupants date back to 827, when Asad ibn al Furat began the siege of Syracuse. It is impossible to determine the development of the town under the Arabs, because they left only a little evidence such as some coins and objects. But the presence of many place names of Arab origin in the region and the presence in the local dialect of words derived from Arabic, clearly show that Islamic culture penetrated deeply into the town ...
... The place names of Norman origin in Sicily constitute real exceptions (...) and so it seems to me well-accepted the hypothesis of an Arab origin of Gulfi, and perhaps we can search a derivation of the name from the root of the [Arabic] adjective ‘galafa’, which gives the plural ‘gulf’, with the meaning of 'place covered by a rich and untouched vegetation.'
... the place where the ancient 'Akrillai' was situated in the 9th century BC or later qualifies since there were many springs in the area and extensive forests near the Dirillo river until the 17th century AD. And a trace of the original Arabic name of 'Gulf' was also found in a notarial document in Latin of the 14th century, mentioning a place called 'De Gulphis'" .
After the Roman era the later presence of the Byzantines can be considered very important, if only because its name was changed to Gulfi. In fact, Antonino de Vita points out that:
"between Stephen of Byzantium and 1120 several centuries elapsed and the original Greek name may have changed during the Byzantine domination , which left many traces of itself, rather than in Arab times, as evidenced by the Christian-Byzantine burial area around it and stretching south from the city; it also suggests the presence of a small church (rectangular, 7 meters x 4.30)" .
L. Chiavola Birnbaum points out that:
"in 4th century CE a Christian community arose at Akrillae. Catacombs of southeast Italy (...) are more numerous than those of Rome” .
See the Chiaramonte Gulfi for a travel guide.
1. See Antonino de Vita, “Ricerche archeologiche in territorio di Chiaramonte Gulfi (Acrillae),” 1954, pp. 87-88.
2. See “Epigraphica,” 2003, p. 12
3. See P. Anello, “L'ambiente greco”, in “Il guerriero di Castiglione di Ragusa”, Roma, 2002, pp. 67-68
4. On these aspects of the ancient Roman military strategy in the early third century BC, See G. Manganaro, “Per una storia della Sicilia Romana”, in "Aufstieg und Niedergang der romischen Welt: Geschichte und Kultur Roms im Spiegel der neueren Forschung," 1972, Vol I, pp. 451-452
5. See B. Pace, “Arte e civiltà della Sicilia antica, ”1935, Vol I, pp. 455-456
6. De Vita, p. 87
7. De Vita, p. 35
8. See L. Chiavola Birnbaum, “Dark Mother: African Origins and Godmothers”, 2001, p. 99
9. See “La grotta di S. Margherita a Chiaramonte Gulfi”, in “le arti figurative nella Sicilia bizantina”, 1962, p. 268
10. See F. Maurici, “Castelli medievali di Sicilia ...”, Sellerio, 1992, p. 306
11. See R. La Franca, “Architettura judaica in Italia: ebraismo, sito, memoria dei luoghi”, Flaccovio, 1994, p. 216
12. De Vita, p. 88
13. De Vita, p. 37