When Ragusan nobility divided Pelješac among each other in 1344, Trpanj was sectioned into 4 parts: two and a half were given to the brothers Dobre and Luka from the Gambe family and the brothers Marko and Petar from the Bucchia family received one and a half.
Both of these families were in the maritime commerce business.
In 1352 when Dobre Gambe died, his part went to his brother Luka and in turn when Luka died in 1358 he requested that his part be sold and the proceeds be given to the monastery in Ston.
The Bucchia brothers also had no inheritors and their parts were sold at public auction in 1395 for 1501 perpers.

Trpanj became property of the Gradi family.
The exact date is not known but it must have been before 24 February 1498, since a building contract with that date describes the construction of a stone house in Trpanj for Stjepan Gradi.
Biagio Stefano Gradi left Trpanj to his son-in-law Jerolim Frano Gundulić.
Hence the Gondola family came into possession of Trpanj on 16 November 1615.
Due to a court order from 18 February 1626 the brothers i, Stefan and Frano Gundulić were ordered to return the dowry of their grandmother to her brothers Miho and Ivan Resti.
To raise the money, the brothers sold half of their Trpanj possessions to Ivan Krste Benessa on 17 July 1632 for 1,590 ducats, stipulating that if in 8 years they manage to return that sum of money to the buyer, the sale will be annulled, which probably happened as Trpanj remained in the Gondola family.

When his brothers died, Biagio found himself sole proprietor of Trpanj, and in order to ensure that Trpanj as a whole remained in his family he made Trpanj an indivisible legal entity protected by a “fideicomis”, a sort of a testamentary trust.

Frano Gondola, who was an Austrian marshal, wrote from Vienna on 22 May 1672 to his friend Marco Bassegli to ask him to get the Republic to name him Duke and as a result to name Trpanj Dukedom of St. Michael of Trpanj.
This was necessary because of his position in Vienna.
Frano died in 1700 before being able to build a summer residence in Trpanj.
Francesco Gondola left the residence in Trpanj to his son Francesco II, who died in Vienna in 1717, without male offspring.

In the spring of 1700 the Gondola family was sued in court by Slava, wife of Paolo Gozze, and the court ordered Trpanj to be divided in two.
Although court documents clearly divide the land and property, the court order was never carried out and the town remained the Gondola fideicomis.
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.

Sigismondo (*1682) died in 1758 leaving Trpanj to his son Sigismondo Domenico Gondola (1712–1800).
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.
Only the gift of olive oil still had to be delivered to the landlord.
The sum of money had to be paid by each family before the celebration of St. Michael's.
That contract was signed a second time for another period of 25 years when the first one expired.

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.
In 1807, the last Count Gondola, Sigismondo Domenico, litigated in the courts of Dubrovnik the fideicomis instituted by Biagio Gondola in 1649 by Pietro Ignazio Gio.
Sorgo-Cerva and Bernardo Caboga by the possession of Trpanj against Sigismondo Ghetaldi-Gondola.

But finally he was succeeded by the sons of Frano Agostino Ghetaldi and Catterina Gondola, Frano Ghetaldi and his sons: Sigismondo Ghetaldi-Gondola (1795–1860) and Mateo Ghetaldi-Gondola (born in 1797), and Trpanj was left to Sigismondo who was later named Baron and podestà of Ragusa for 13 years.
He had 3 children: Frano, Gino (1835–1891) and Mar
When Ragusan nobility divided Pelješac among each other in 1344, Trpanj was sectioned into 4 parts: two and a half were given to the brothers Dobre and Luka from the Gambe family and the brothers Marko and Petar from the Bucchia family received one and a half. Both of these families were in the maritime commerce business. In 1352 when Dobre Gambe died, his part went to his brother Luka and in turn when Luka died in 1358 he requested that his part be sold and the proceeds be given to the monastery in Ston. The Bucchia brothers also had no inheritors and their parts were sold at public auction in 1395 for 1501 perpers.
Trpanj became property of the Gradi family. The exact date is not known but it must have been before 24 February 1498, since a building contract with that date describes the construction of a stone house in Trpanj for Stjepan Gradi. Biagio Stefano Gradi left Trpanj to his son-in-law Jerolim Frano Gundulić. Hence the Gondola family came into possession of Trpanj on 16 November 1615. Due to a court order from 18 February 1626 the brothers i, Stefan and Frano Gundulić were ordered to return the dowry of their grandmother to her brothers Miho and Ivan Resti. To raise the money, the brothers sold half of their Trpanj possessions to Ivan Krste Benessa on 17 July 1632 for 1,590 ducats, stipulating that if in 8 years they manage to return that sum of money to the buyer, the sale will be annulled, which probably happened as Trpanj remained in the Gondola family.
When his brothers died, Biagio found himself sole proprietor of Trpanj, and in order to ensure that Trpanj as a whole remained in his family he made Trpanj an indivisible legal entity protected by a “fideicomis”, a sort of a testamentary trust.
Frano Gondola, who was an Austrian marshal, wrote from Vienna on 22 May 1672 to his friend Marco Bassegli to ask him to get the Republic to name him Duke and as a result to name Trpanj Dukedom of St. Michael of Trpanj. This was necessary because of his position in Vienna. Frano died in 1700 before being able to build a summer residence in Trpanj. Francesco Gondola left the residence in Trpanj to his son Francesco II, who died in Vienna in 1717, without male offspring.
In the spring of 1700 the Gondola family was sued in court by Slava, wife of Paolo Gozze, and the court ordered Trpanj to be divided in two. Although court documents clearly divide the land and property, the court order was never carried out and the town remained the Gondola fideicomis. 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.
Sigismondo (*1682) died in 1758 leaving Trpanj to his son Sigismondo Domenico Gondola (1712–1800). 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. Only the gift of olive oil still had to be delivered to the landlord. The sum of money had to be paid by each family before the celebration of St. Michael's. That contract was signed a second time for another period of 25 years when the first one expired.
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. In 1807, the last Count Gondola, Sigismondo Domenico, litigated in the courts of Dubrovnik the fideicomis instituted by Biagio Gondola in 1649 by Pietro Ignazio Gio. Sorgo-Cerva and Bernardo Caboga by the possession of Trpanj against Sigismondo Ghetaldi-Gondola. 
But finally he was succeeded by the sons of Frano Agostino Ghetaldi and Catterina Gondola, Frano Ghetaldi and his sons: Sigismondo Ghetaldi-Gondola (1795–1860) and Mateo Ghetaldi-Gondola (born in 1797), and Trpanj was left to Sigismondo who was later named Baron and podestà of Ragusa for 13 years. He had 3 children: Frano, Gino (1835–1891) and Mar
Trpanj