The first prince to be concerned with city planning avant-la-lettre was Mircea Ciobanul (Mircea the Shepherd, 1545-1554). During his reign, the city boundaries grow more clearly defined, by oaken walls; within the city, properties and terrains are also delimited by stone marks. This prince was also an advocate of Orthodoxy, being the founder of the Church of the ancient Princely Court, among others. However, the religious fervour did not spare him the misfortune of being disavowed by the Turks in 1554, for reasons that remain unclear. Afterwards, the Ottoman army that entered the city murdered all the courtiers, looted the city and set it on fire. As we will see, such events were not rare during the ensuing century.

Bucharest is also stricly related to the reign of Mihai Viteazul (Mihai the Brave, 1593-1601), the ex-Ban of Oltenia, who will live to be the first prince who achieved national unity. Mihai preferred to reside in Tirgoviste and that for a cause: in November 1594 he sends for Turk creditors at the Bucharest treasury to acquit his debts and he murders them one by one ? we have to agree, it is quit: an efficient, if radical, manner to settle one?s accounts.

Thereon, his relations to the Ottoman empire become rather tense, and Bucharest bears the costs at their hardest. In the summer of 1595, though victor over the Turks at Calugareni (South of Bucharest), Mihai is contrived to retreat in the Carpathians, while Sinan Pasha, the ruler of the Turks, takes Bucharest over. The first measure taken by the Turks is to fortify the citadel and prepare for a lengthy stay. Mihai, with support from the army troops of Sigismund Bathory (prince of Transylvania), recuperates the city, but the Turks set it on fire before leaving it. No sooner had households been rebuilt than, in the fall of 1596, the Tartars unexpectedly strike as well and Bucharest is set on fire. From a historical perspective, these tragedies have an interesting morale: the city already manifested a remarkable dynamism tightly related to its regenerating force. All evidence points to the fact that after all the looting and setting on fire, houses and shops were restored in no time. It was more difficult to do the same with churches, because funds were not that easily raised in this case. Even if, generally speaking, Bucharest dwellers were in awe of God and in the habit of church-going, they were also practising, without even knowing it, the philosophy of liberalism.