Kaliakra

Kaliakra occupies a narrow peninsula that thrusts far out into the sea. The medieval town was divided into three parts by three successive lines of defence running across the cape from its eastern to its western shore: a suburb, an outer town and a citadel. Best preserved is the inner, southernmost wall, which guarded the citadel. Excavations have also revealed a medieval church and traces of lively economic life.

In the thirteenth century the centre of this district was Karvuna — the land of Karvuna is already named in Ivan Asen II's Dubrovnik charter of 1230. By the mid-fourteenth century the domain, grown from an appanage dependent on the tsar of Tarnovo, was ruled by three brothers of Bulgarian-Cuman descent — Balik, Theodore and Dobrotitsa — and was drifting ever further from Tarnovo.

The brothers entered high politics during the Byzantine civil war. In 1346 the regent Anne of Savoy asked Balik for help against John Kantakouzenos, and he sent his two brothers to Constantinople with a thousand picked soldiers. The empress received them warmly, married Dobrotitsa to the daughter of the grand duke Alexios Apokaukos and appointed him commander of the Byzantine army. At the head of combined Bulgarian and Byzantine forces Dobrotitsa attacked Selymbria, but in the battle with Kantakouzenos' troops he did not prove a good general.

By 1360 Dobrotitsa had returned home and was ruling in his brother's place — a Genoese document of 20 October 1360 speaks of "the pirate galleys of lord Dobrotitsa". His capital was Kaliakra, and his domains roughly matched today's Dobruja, which bears his name in its Turkish form. He held the title of despot — according to Ivan Biliarski probably granted by Ivan Alexander — struck his own coins and conducted himself as a Balkan ruler in his own right.

Dobrotitsa was one of the mediators in settling the great crisis of 1365–1369. Together with the Wallachian voivode Vladislav Vlaicu he took part in freeing Vidin from the Hungarians, and after Amadeus of Savoy's campaign of 1366 he received Varna, Emona and Kozyak, and around 1370 he added Drastar. With this the despot of the Dobruja held the central and northern part of the coast — Emona, Varna, Kavarna and Kaliakra.

The Black Sea coast was by now the scene of the commercial dominance of Venice and above all Genoa, and here Dobrotitsa completely displaced Tarnovo. Between 11 and 15 November 1373 his daughter married Michael Palaiologos, son of Emperor John V. The despot conceived a bold plan: with the help of Venice, which was on bad terms with Trebizond, to set his son-in-law on the throne of Trebizond in place of Alexios III Komnenos. The plan collapsed when in 1376 Dobrotitsa's son John Terter, governor of Drastar, sided with Andronikos IV and killed Michael Palaiologos.

Relations with Genoa remained strained into the 1380s; three Venetian documents of the period speak of Genoese measures against anyone who went to the despot's lands. To Constantinople Dobrotitsa remained a "barbarian": the letter-writing manual of the Ecumenical Patriarchate of 1386 notes that in addressing barbarian despots like him their name was written out. The German captive Schiltberger later wrote of "three Bulgarias", the third lying where the Danube flows into the sea, with its capital at Kaliakra.

Around 1385 Dobrotitsa was succeeded by his son Ivanko, who in 1387 concluded a treaty with Genoa granting the Genoese broad privileges. In 1388 Ali Pasha's campaign touched the despotate only in part: the attack on Varna was not seriously organised and the Turks did not enter Ivanko's lands. Soon, however, the Dobruja domain too fell to the Ottomans — shortly after the tsardoms of Tarnovo and Vidin.