Another theory draws the origin of the name from δρεπάνη : drepánē, an Ancient Greek word for sickle, which is the shape formed by the cliffs surrounding the town's harbor.

Examples of prehistoric pottery, evidence that the site may have been inhabited by an urban-type society, were found on the slopes of Gradina, the small hill overlooking the port.

Life in the area may not have been easy as it is located between barren cliffs to the north and the Miloševica, Viter and Prvač Dol hills to the south.

According to the Dubrovnik historian Jakov Lukarić, the ancient fortress, Tarpano or Tarponio, was destroyed by Julius Caesar while he was fighting the Illyrians.

During the Goth rule of Dalmatia in the 6th century, Byzantine emperor Justinian I built a series of defenses along the coast, including the one on the top of Gradina, in an attempt to reclaim the lands lost to invading tribes and to ensure safe passage of trade.

Greek vessels used the channel to transport ingredients for the production of incense to Corinth, while Romans mostly used it to trade wine in amphoras.

The Republic of Ragusa (Dubrovnik) initiated diplomatic action to gain international recognition of the newly occupied lands.

Serf daughters were sent to work as maids in noble families, thus bringing culture and fashion trends from the city to the countryside.

Sigismondo was sued again, this time by his serfs from Trpanj, in the spring of 1741, for a variety of unlawful actions ranging from requiring free fishing to confiscation of boats and other property and interference in their commerce.

In order to avoid constant lawsuits by his financially powerful serfs, he struck a deal on 4 July 1765 whereby the 70 Trpanj families were to pay a sum of money for the following 25 years, instead of performing services or giving gifts to Gundulić.

Sigismondo Domenico Gondola, who was to die in 1800, had no inheritors so he adopted his sister's (Katarina) son Frano Agostino Ghetaldi in 1787.

Trpanj remained the property of the Ghetaldi-Gondola family and its inhabitants would pay the landlord a fixed sum of money every year instead of the traditional services and gifts in nature until the Trpanj residents, the first on Pelješac, decided to legally buy their town from the landlord and relieve themselves of official serfdom in 1856.

A staircase and path that lead to the fortress and the observatory was built in 1936 although it is presently hard to gain access to, due to residential buildings that make it less obvious.

The Trpanj born bishop Dživo Natali inspected the church in 1684 and forbade mass services till main altar renovations were not carried out.

The Vručica priest don Juraj Gabrić confirms having received the gold from the state treasury and those are the oldest references found for this church.

It was a small church with probably one wooden altar displaying a group of saints: St Michael with a scale, to the right St. Peter with keys and to the left St. Paul.

Prince Joseph II of Liechtenstein who frequently came to Trpanj to hunt for čaglje (a wild dog native of Pelješac resembling a hyena) made a gift of 2 bells in 1888.

Stefan Gundulić-Gondola (the uncle of writer and Duke Ivan Gundulić) died in 1647 and the first mention of the church is found in the bishop's visitation of 29 April 1679.

It is noted that the church suffers from damage from humidity so instructions are given for two windows to be equipped with iron bars to allow free flow of air.

The town council built a dome on the church and installed a public clock and was responsible for its accuracy following a contract signed in 1874.

Bishop Milković in his 1751 visit notes that the church has a well equipped altar, a good silver chalice, and all other items of cult.

The inscription also says in Croatian: “buduci da ga bili pokrili valovi, od smrti osloboden” meaning “delivered from death having been covered by the waves [sea].” Kleme Cvitanović (1799–1877) was born in Drasnica not far from Makarska but married Frana Iveta from Trpanj and relocated there.

This church, dedicated to the protector of sailors, was built at the onset of the golden age of Trpanj's sail boats specializing in mall coastal commerce.

The Narodni List (the national Paper) in its no.89 edition from 7 November 1903 describes the marble work of art as both artistically pleasing and patriotic, as it displays elements from Croatian folklore.

Fishing's importance is evidenced from a letter from Matija Andricic who wrote to the Council in 1765 to be absolved from paying taxes that year as the total catch did not exceed 50 barrels.

In the 18th century owners of fishing vessels were from the following families: Augustinović, Andricić, Balovi, Barbica, Barac, Bergando, Belin, Butirić, Certić, Franković, Ferri, Iveta, Jerić, Klarić, Kresić, Kulišić, Mirković, Nesanović, Senko, Simonetti, Skoko and Zimić.

In February 1669, the Ragusan Senate orders that officials be sent to Trpanj to bring two sail ships with crew because they have not answered the call to transport construction material for the restoration of the place.

From 1677 to 1797 there were 41 known sailors from Trpanj in the Venetian fleet and two known ship commanders Grga Ivana Frankovic and Mato Nika Mrčić.

Many Trpanj priests were co-owners of sailships notably: Miho Fabrelli Iveta, Antun Simonetti, Mato Nesanović, Nikola Augustinović, Baldo Kresic, Andrija Kalais and Ivan Klaric-Mirkovic.

In the 18th century, in Senigallia near Ancona, merchants from Trpanj had their own warehouses for storing fish and other goods during the local fair.