Vincenzo Florio, scion of a prominent Sicilian family, longed to travel the world beyond Sicily. As soon as he could he traveled to Germany and France. While in Paris he came upon a showroom that contained a machine he had never seen before. The machine was a de Dion motor tricycles which he promptly purchased and had shipped back to Palermo. The new contraption caused quite a sensation as it was unloaded onto the dock. Unfortunately there it stayed due to the fact that there was not any gasoline available in all of Sicily! Urgent cables to Paris finally brought a shipment of the precious fuel. After the initial thrill of driving his new toy began to wear off he decided to have a race. The only problem was that his was the sole motor car on the Island which would make for a poor race. It was decided that he would organize a handicap race between his car, a cyclist and a horseman. The cyclist was the first to drop out with cramps which put Vincenzo and his car in the lead, but the lead was short lived when his engine began to over heat. Scoring one last win in the battle of horse and machine the horseman galloped past to take the victory. Rather than wallowing in defeat Vicenzo vowed to return from France with a real motor car. He tried many different cars but the hilly Sicilian countryside proved too much for the fragile cars. Finally he turned to a new Italian manufacturer, Fiat. The turn of the century Fiat was a company that believed in service and would send a representative to each customer to ensure that the customer was properly trained in the care and maintenance of their new car. To Sicily they sent a young apprentice named Felice Nazzaro who would soon make a name for himself as one of the first great racing car drivers. Nazzaro and Vincenzo became fast friends. He induced Nazzaro to stay in Sicily to take care of his growing stable of cars. Vincenzo's rich friends did not sit still while all of this was taking place, they also bought cars and had them shipped to Sicily. Soon races were organized in Favorita Park. Feeling himself sufficiently experienced he decided to order a real racing car with which he could compete in races in the rest of Europe. Fiat fearing that Vincenzo was a still to young and experienced would not sell him a car. After much searching he bought a dis-assembled Panhard and had it rebuilt. Nazzaro brought the new car up to race readiness and in its first competition, Vicenzo Florio won a speed trial in Padua. Emboldened by this easy win he prepared to enter the infamous 1903 Paris to Madrid race. His brother Ignazio, hearing of this conspired to prevent his under-age brother from leaving the island and may actually have saved his life. The race was stopped short of the end after numerous fatal accidents that took the lives of spectators and drivers including the Renault brother Marcel. The next big race on the calendar was the race in Brescia which Vincenzo entered without his older brothers knowledge and in which he finished a respectable third. After he was finally judged to be of age and no longer the responsibility of his brother, Vincenzo entered every race that he could including the Kaiserpreis, the first French Grand Prix and the Gordon Bennet cup. While competing in one of these races he met a man by the name of Henri Desgrange who was the editor of l'Auto. Desgrange suggested to Vincenzo that he should organize a international race in Sicily.   

The Targa Florio was not so much a race as it was an ordeal. Established in 1906  a single lap was approximately 92 miles. Besides the course which traversed mountain roads unchanged since the Punic Wars, there were severe changes in climate, bandits and wolves. Each hairpin competed with a sheer abyss for the driver's attention over a 3 lap race of 277 miles. Initially there were few rules and the event was open to standard cars of which at least ten identical models had been built. The first race was held on the sixth of May. Only ten cars made it to the starting line due to a dock strike in Genoa. (ed. Some things never change) The race would be one of attrition that included among its victims, Vincenzo. On of the entrants was a husband and wife team, the wife serving as the mechanic. Unfortunately no record of their experiences exist. Two cars suffered from water being mistaken for gasoline and required the complete draining of each car's fuel tanks.   After nine hours the race was over and the winner for the Italia team was Alessandro Cagno at an average speed of 29.06 mph. The race proved very popular with the local populace and next years race brought more than 50 entries. In 1907 the race was held on April 22. Like its younger cousin, the Mille Miglia, this race could only be won by driving flat out and after the inaugural race the returning teams had a better understanding of the conditions in which this race was run. Fiat's entry led by Vincenzo Lancia and Felice Nazzaro would be one of the early favorites. At the end of the first lap it was Lancia in the Fiat in the lead. After a slow start the Darracq of Louis Wagner began to gain on the leaders. Soon he passed the first lap leader, Lancia, only to find himself second behind Nazzaro. Still he came, and soon he could see Nazzaro just ahead of him. But alas his engine revs shot up yet his car slowed down and then he found the reason, a broken drive shaft. Nazzaro won the second Targa Florio and since he was known to many of the locals, his victory was very popular with the fans. The third Targa Florio only had thirteen entries after the French decided to stay away. The race was won by Vincenzo Trucco in a Isotta Fraschini. The fourth Targa was almost canceled when an earthquake struck along the eastern coast and the town of Messina. The deaths of more than 155,000 of its citizens was the result. Still Vincenzo was able to keep the race going for the next few years but the future looked bleak. In desperation Vincenzo changed the circuit to one lap of approximately 628 miles. Slowly the race was brought back to life only to be stopped during World War 1. After the war the organizers were determined to restart the race so that in November of 1919 a new Targa Florio would be reborn. The circuit was shortened to 67 miles but the race was increased to four laps for a total of 268 miles. The war had deprived the Targa Florio of the great Peugeot driver Georges Boillot who was shot down in a dogfight with a squadron of German fighters. In his place was his brother André Boillot driving a 2 1/2 liter Peugeot originally built before the war. Another entrant of later note was a twenty-one year old driver, Enzo Ferrari, driving a Lancia in his first major race. The weather for the November race was abysmal and saw Antonio Ascari disappear into the distance, or more accurately into a ravine where he was rescued after the race. The circuit was a muddy mess as were the drivers. But Rene Thomas, driving a Ballot was serenely in the lead, or at least he was until his frantic crew was finally able to warn him of a fast approaching André Boillot. But for Thomas it was not enough as the Peugeot of Boillot flashed past. Only a mistake by Boillot could save Rene Thomas now, but still he could not give up and thus increased his speed. For Boillot all that was left was a mad dash down the finishing straight. Racing to the point of exhaustion he braked for the final corner - but he had braked two late for the treacherous conditions and the back of the car spun and hit the grandstand just thirty feet from the finish line. Dazed and bloodied they Boillot and his mechanic were pushed free from the structure and crossed the line in reverse! Shouts of protest greeted the crew but out from the crowd walked Ernest Ballot, the owner of the rival and second place car convinced a dejected André Boillot to return to his car, drive back to the point of their crash and re-cross the line in the right direction. Sacrificing a possible victory for his own car, Ernest Ballot's decision met with the approval of the crowd and André Boillot was declared the winner where upon he fainted straight away.

The race in 1921 saw the Targa Florio come of finally come of age with the appearance of the first full works team. Alfa Romeo entered four specially prepared cars while Fiat entered two new cars. But it was the amateur Count Masetti and Max Sailor driving a Mercedes who dominated the race. The Mercedes was a factory entrant in all but name. The battle between the two was finally won by Masetti in a "one off" Grand Prix Fiat. He repeated his feat the following year. In 1924 Alfred Neubauer finished thirteenth with his co-driver Ferdinand Porsche while Christian Werner won in a Mercedes after Antonio Ascari was forced to push his stricken car over the line. Tazio Nuvolari and Achille Varzi continued their intense rivalry at the Targa Florio in 1930. Both drove Alfas but Varzi's was the more powerful P.2. At the start of the race Varzi stormed into the lead but trouble struck when his spare wheel worked itself lose along the jarring mountain roads. The wheel would puncture his fuel tank causing him to stop more often for fuel. At the last stop his riding mechanic grabbed a spare fuel can. While racing along a downhill stretch his mechanic attempted to refuel the car. Unfortunately a high IQ was not a prerequisite for being a racing mechanic and the car caught fire when some of the fuel spilled onto the hot exhaust. Varzi unwilling to stop and lose the race to his bitter rival continued on while his mechanic beat the fires furiously with his seat cushion. Thus they won the race in truly spectacular fashion.

Mercedes had decided to quit racing after the 1955 season but one last major attempt was made to wrest the sports car championship from Ferrari. That attempt would be made at the Targa Florio. Led by Alfred Neubauer and his team of Fangio, Kling, Moss, Collins, Fitch and Titterington. They had five 300SLR's, more than a dozen private cars, 45 mechanics and seven trucks. Because the roads were not closed prior to the race practice involved avoiding, pedestrians, wagons and the odd goat. The rules set for the three pairs of drivers was every man for themselves. This years Targa Florio would entail 13 laps over a 44.64-mille circuit for a total of 580.32 miles. The teams of drivers were expected to negotiate approximately 10,000 curves and almost 10 hours of driving combined. Neubauer was planning on each driver being able to run 4 lap stints. At the start of the race Moss set a blistering pace and broke the course record by two and a half minutes. Though his car was one of the last to be flagged off, he had passed everyone by the end of the first lap. Castellotti's Ferrari split the Mercedes of Moss and Fangio. At the end of the fourth lap Castellotti was in first place and Moss was in a ditch. Moss had crashed but the Mercedes was still in working order if slightly bruised. After help from some spectators Moss was back on the road but now in fourth place. Collins exchanged places with Moss and took up the chase. Fangio passed the leading Ferrari and handed his car to Kling. Mercedes were now in first, third and fourth. Trouble struck again when Collins drove straight up a stone wall, his front wheels spinning in the air. Fortunately he was able to put his car in reverse and rejoin the battle. Collins worked his way up to first before returning the car to Moss. Moss drove the only way that he knew how and won going away or in the words of Peter Collins "despite Stirling's efforts and my own to write the machine off!" Mercedes won the race and with it the sports car championship only to quit racing for the second time. The race would continue until 1973. That race was won by a Porsche driven by Muller/Van Lennep.