On the next day, the two fleets maneuvered and fought off Gallipoli, but during the evening, Loredan managed to contact the Ottoman authorities and inform them of his diplomatic mission.

[1] The Republic of Venice, as the premier maritime and commercial power in the area, endeavoured to renew the treaties it had concluded with Mehmed's predecessors during the civil war, and in May 1414, its bailo (resident ambassador) in the Byzantine capital, Constantinople, Francesco Foscarini, was instructed to proceed to the Sultan's court to that effect.

[2] In the meantime, tensions between the two powers mounted, as the Ottomans moved to re-establish a sizeable navy and launched several raids that challenged Venetian naval hegemony in the Aegean Sea.

[3] During his 1414 campaign in Anatolia, Mehmed came to Smyrna, where several of the most important Latin rulers of the Aegean—the Genoese lords of the northeastern Aegean islands of Chios, Phokaia, and Lesbos, and even the Grand Master of the Knights Hospitaller of Rhodes—came to do him obeisance.

The Ottomans pillaged the colony's capital, Negroponte, taking almost all its inhabitants prisoner; out of some 2,000 captives, the Republic was able after years to secure the release of only 200, mostly elderly men, women, and children, the rest having been sold as slaves.

[10] Furthermore, in the autumn of 1415, ostensibly in retaliation for Zeno's attacks, an Ottoman fleet of 42 ships—6 galleys, 26 galleots, and the rest smaller brigantines—tried to intercept a Venetian merchant convoy coming from the Black Sea at the island of Tenedos, at the southern entrance of the Dardanelles.

The Venetian vessels were delayed at Constantinople by bad weather, but managed to pass through the Ottoman fleet and outrun its pursuit to the safety of Negroponte.

[12][14] The raids spread considerable panic: Lepanto on the western coast of Greece was deserted, and at Venice no one was found who wanted to contract, not even for a small sum, the right to equip merchant galleys bound for Constantinople, or the Black Sea ports of Tana and Trebizond.

Due to the lucrative trade opportunities these ports offered, the contracts ordinarily fetched prices of up to 2,000 ducats, but now the Venetian government was obliged to supply armed escorts for the merchant galleys at its own expense.

A half-percent levy was raised on goods, soldiers and crossbowmen were recruited, and the experienced Pietro Loredan was appointed Captain of the Gulf, at the head of a fleet of fifteen galleys; five were to be equipped[a] in Venice, four at Candia (Crete), and one each at Negroponte, Napoli di Romania (Nauplia), Andros, and Corfu.

[18][19] Loredan's brother Giorgio, Jacopo Barbarigo, Cristoforo Dandolo, and Pietro Contarini were appointed as sopracomiti (galley captains), while Andrea Foscolo and Dolfino Venier were designated as provveditori (commissioners) of the fleet and ambassadors to the Sultan.

[22] Loredan's appointment was unusual, as he had served recently as Captain of the Gulf, and law forbade anyone who had held the position from holding the same for three years after; the Great Council overrode this rule due to the de facto state of war with the Ottomans.

In a further move calculated to bolster Loredan's authority (and appeal to his vanity), an old rule that had fallen into disuse was revived, whereby only the captain-general had the right to carry the Banner of Saint Mark on his flagship, rather than every sopracomito.

[28] Bayezid aimed to use his warships in Gallipoli to control (and tax) the passage of shipping through the Dardanelles, an ambition which brought him into direct conflict with Venetian interests in the area.

[38][b] According to Loredan's letter, his fleet—four galleys from Venice, four from Candia, and one each from Negroponte and Napoli di Romania[c][40]—was delayed by contrary winds and reached Tenedos on 24 May, and did not enter the Dardanelles until the 27th, when they arrived near Gallipoli.

[43][44] Loredan then sent a messenger to the Ottoman fleet commander to complain about the attack, insisting that his intentions were pacific, and that his sole purpose was to convey the two ambassadors to the Sultan.

The Ottoman dignitaries reassured Thomas of their good will, and proposed to provide an armed escort for the ambassadors to bring them to the court of Sultan Mehmed.

[51] During the same night, the Turkish ships left their anchorage and deployed in a line of battle opposite the Venetians, without however making any hostile moves; but at and around Gallipoli, numerous troop movements could be observed, with soldiers boarding vessels of every kind.

Its crew offered determined resistance, and the other Ottoman galleys came astern of Loredan's ship to his left, and launched volleys of arrows against him and his men.

[62] The Venetians defeated the Ottoman fleet, killing its commander Çali Bey (Cialasi-beg Zeberth) and many of the captains and crews, and capturing six great galleys and nine galleots, according to Loredan's account.

[63] Among the captive Ottoman crews were found to be many Christians—Genoese, Catalans, Cretans, Provencals, and Sicilians—who were all executed as renegades by hanging from the yardarms, while a certain Giorgio Calergi, who had participated in a revolt against Venice in Crete, was quartered at the deck of Loredan's flagship.

[72] At Tenedos, Loredan held a council of war, where the prevailing opinion was to return to Negroponte for provisions, for offloading the wounded, and for selling three of the galleys for prize money for the crews.

He sent his brother with his ship to bring the more heavily wounded to Negroponte, and burned three of the captured galleys since they were too much of a burden—in his letter to the Signoria, he expressed the hope that his men would still be recompensed for them, his shipwrights estimating their value at 600 gold ducats.

[74] At the same time, there was no appetite for a prolonged conflict: the Republic was still menaced by the Hungarian king Sigismund in Friuli, mindful of rising Genoese influence in Greece, and wary of the expense maintaining a fleet entailed.

[76] Landing the ambassadors was delayed until July,[77] but was in the end successful, possibly via Constantinople,[78] where Loredan reports having received precious relics from Emperor Manuel II Palaiologos as a reward for his victory.

To this the Venetians, who regarded Venier's agreement as void, objected that only the old and infirm were released, while the rest had been sold to slavery; and that no comparison could be made between people captured during a raid with prisoners taken "in a just war".

While they inflicted significant damage to the fort with their missiles, the Venetians were prevented from landing due to the presence of Hamza Bey, the brother of the Grand Vizier Bayezid Pasha, with 10,000 men.

[93] Even so, during the Siege of Thessalonica in 1422–1430 and subsequent conflicts over the course of the century, "the Venetians would learn to their discomfiture that naval superiority alone could not guarantee an everlasting position of strength in the eastern Mediterranean".