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The Florentines, having occupied San Miniato, held a council of war to decide whether they should attack Pisa or the army of Castruccio, and, having weighed the difficulties of both courses, they decided upon the latter. The river Arno was at that time low enough to be fordable, yet the water reached to the shoulders of the infantrymen and to the saddles of the horsemen. On the morning of 10 June 1328, the Florentines commenced the battle by ordering forward a number of cavalry and ten thousand infantry. Castruccio, whose plan of action was fixed, and who well knew what to do, at once attacked the Florentines with five thousand infantry and three thousand horsemen, not allowing them to issue from the river before he charged them; he also sent one thousand light infantry up the river bank, and the same number down the Arno. The infantry of the Florentines were so much impeded by their arms and the water that they were not able to mount the banks of the river, whilst the cavalry had made the passage of the river more difficult for the others, by reason of the few who had crossed having broken up the bed of the river, and this being deep with mud, many of the horses rolled over with their riders and many of them had stuck so fast that they could not move. When the Florentine captains saw the difficulties their men were meeting, they withdrew them and moved higher up the river, hoping to find the river bed less treacherous and the banks more adapted for landing. These men were met at the bank by the forces which Castruccio had already sent forward, who, being light armed with bucklers and javelins in their hands, let fly with tremendous shouts into the faces and bodies of the cavalry. The horses, alarmed by the noise and the wounds, would not move forward, and trampled each other in great confusion.

In the early part of May 1328, the Florentines put in motion this army and quickly occupied Lastra, Signa, Montelupo, and Empoli, passing from thence on to San Miniato. When Castruccio heard of the enormous army which the Florentines were sending against him, he was in no degree alarmed, believing that the time had now arrived when Fortune would deliver the empire of Tuscany into his hands, for he had no reason to think that his enemy would make a better fight, or had better prospects of success, than at Pisa or Serravalle. He assembled twenty thousand foot soldiers and four thousand horsemen, and with this army went to Fucecchio, whilst he sent Pagolo Guinigi to Pisa with five thousand infantry. Fucecchio has a stronger position than any other town in the Pisan district, owing to its situation between the rivers Arno and Gusciana and its slight elevation above the surrounding plain. Moreover, the enemy could not hinder its being victualled unless they divided their forces, nor could they approach it either from the direction of Lucca or Pisa, nor could they get through to Pisa, or attack Castruccio’s forces except at a disadvantage. In one case they would find themselves placed between his two armies, the one under his own command and the other under Pagolo, and in the other case they would have to cross the Arno to get to close quarters with the enemy, an undertaking of great hazard. In order to tempt the Florentines to take this latter course, Castruccio withdrew his men from the banks of the river and placed them under the walls of Fucecchio, leaving a wide expanse of land between them and the river.

Shortly after this the Florentines were relieved in some degree of the pressure of Castruccio’s army, owing to his being compelled to leave his positions before Florence and march on Pisa, in order to suppress a conspiracy that had been raised against him by Benedetto Lanfranchi, one of the first men in Pisa, who could not endure that his fatherland should be under the dominion of the Lucchese. He had formed this conspiracy, intending to seize the citadel, kill the partisans of Castruccio, and drive out the garrison. As, however, in a conspiracy paucity of numbers is essential to secrecy, so for its execution a few are not sufficient, and in seeking more adherents to his conspiracy Lanfranchi encountered a person who revealed the design to Castruccio. This betrayal cannot be passed by without severe reproach to Bonifacio Cerchi and Giovanni Guidi, two Florentine exiles who were suffering their banishment in Pisa. Thereupon Castruccio seized Benedetto and put him to death, and beheaded many other noble citizens, and drove their families into exile. It now appeared to Castruccio that both Pisa and Pistoia were thoroughly disaffected; he employed much thought and energy upon securing his position there, and this gave the Florentines their opportunity to reorganize their army, and to await the coming of Carlo, the son of the King of Naples. When Carlo arrived they decided to lose no more time, and assembled a great army of more than thirty thousand infantry and ten thousand cavalry—having called to their aid every Guelph there was in Italy. They consulted whether they should attack Pistoia or Pisa first, and decided that it would be better to march on the latter—a course, owing to the recent conspiracy, more likely to succeed, and of more advantage to them, because they believed that the surrender of Pistoia would follow the acquisition of Pisa.

Retreat had been impossible, with the mountains on both flanks, whilst in front were their enemies, and in the rear their friends. When Castruccio saw that his men were unable to strike a decisive blow at the enemy and put them to flight, he sent one thousand infantrymen round by the castle, with orders to join the four hundred horsemen he had previously dispatched there, and commanded the whole force to fall upon the flank of the enemy. These orders they carried out with such fury that the Florentines could not sustain the attack, but gave way, and were soon in full retreat—conquered more by their unfortunate position than by the valour of their enemy. Those in the rear turned towards Pistoia, and spread through the plains, each man seeking only his own safety. The defeat was complete and very sanguinary. Many captains were taken prisoners, among whom were Bandini dei Rossi, Francesco Brunelleschi, and Giovanni della Tosa, all Florentine noblemen, with many Tuscans and Neapolitans who fought on the Florentine side, having been sent by King Ruberto to assist the Guelphs. Immediately the Pistoians heard of this defeat they drove out the friends of the Guelphs, and surrendered to Castruccio. He was not content with occupying Prato and all the castles on the plains on both sides of the Arno, but marched his army into the plain of Peretola, about two miles from Florence. Here he remained many days, dividing the spoils, and celebrating his victory with feasts and games, holding horse races, and foot races for men and women. He also struck medals in commemoration of the defeat of the Florentines. He endeavoured to corrupt some of the citizens of Florence, who were to open the city gates at night; but the conspiracy was discovered, and the participators in it taken and beheaded, among whom were Tommaso Lupacci and Lambertuccio Frescobaldi.

Castruccio, having prepared everything, had now to encourage the Florentines to persist in their desire to carry the seat of war away from Pistoia into the Val di Nievole, therefore he did not move his army from Montecarlo. Thus the Florentines hurried on until they reached their encampment under Serravalle, intending to cross the hill on the following morning. In the meantime, Castruccio had seized the castle at night, had also moved his army from Montecarlo, and marching from thence at midnight in dead silence, had reached the foot of Serravalle: thus he and the Florentines commenced the ascent of the hill at the same time in the morning. Castruccio sent forward his infantry by the main road, and a troop of four hundred horsemen by a path on the left towards the castle. The Florentines sent forward four hundred cavalry ahead of their army which was following, never expecting to find Castruccio in possession of the hill, nor were they aware of his having seized the castle. Thus it happened that the Florentine horsemen mounting the hill were completely taken by surprise when they discovered the infantry of Castruccio, and so close were they upon it they had scarcely time to pull down their visors. It was a case of unready soldiers being attacked by ready, and they were assailed with such vigour that with difficulty they could hold their own, although some few of them got through. When the noise of the fighting reached the Florentine camp below, it was filled with confusion. The cavalry and infantry became inextricably mixed: the captains were unable to get their men either backward or forward, owing to the narrowness of the pass, and amid all this tumult no one knew what ought to be done or what could be done. In a short time the cavalry who were engaged with the enemy’s infantry were scattered or killed without having made any effective defence because of their unfortunate position, although in sheer desperation they had offered a stout resistance.

During this time the Florentines, who were much enraged that Castruccio should have seized Pistoia during the truce, considered how they could tempt the city to rebel, to do which they thought would not be difficult in his absence. Among the exiled Pistoians in Florence were Baldo Cecchi and Jacopo Baldini, both men of leading and ready to face danger. These men kept up communications with their friends in Pistoia, and with the aid of the Florentines entered the city by night, and after driving out some of Castruccio’s officials and partisans, and killing others, they restored the city to its freedom. The news of this greatly angered Castruccio, and taking leave of Enrico, he pressed on in great haste to Pistoia. When the Florentines heard of his return, knowing that he would lose no time, they decided to intercept him with their forces in the Val di Nievole, under the belief that by doing so they would cut off his road to Pistoia. Assembling a great army of the supporters of the Guelph cause, the Florentines entered the Pistoian territories. On the other hand, Castruccio reached Montecarlo with his army; and having heard where the Florentines’ lay, he decided not to encounter it in the plains of Pistoia, nor to await it in the plains of Pescia, but, as far as he possibly could, to attack it boldly in the Pass of Serravalle. He believed that if he succeeded in this design, victory was assured, although he was informed that the Florentines had thirty thousand men, whilst he had only twelve thousand. Although he had every confidence in his own abilities and the valour of his troops, yet he hesitated to attack his enemy in the open lest he should be overwhelmed by numbers.

The Vitelli and Orsini having received orders to wait for the duke, and to honour him in person, sent away their men to several castles distant from Sinigalia about six miles, so that room could be made for the men of the duke; and they left in Sinigalia only Oliverotto and his band, which consisted of one thousand infantry and one hundred and fifty horsemen, who were quartered in the suburb mentioned above. Matters having been thus arranged, the Duke Valentino left for Sinigalia, and when the leaders of the cavalry reached the bridge they did not pass over, but having opened it, one portion wheeled towards the river and the other towards the country, and a way was left in the middle through which the infantry passed, without stopping, into the town.