The first Centomiglia organised  by the Circolo Vela Gargnano took place in 1951. It is the tour of Lake Garda  and its name recalls the “Mille Miglia” motor race, and just  like in this competition, everyone is free to take part.
The first competition,  which saw 17 boats at the start, was won by the “6 metre” “Airone”of  Umberto  Peretti Colò, skipper of the “Compagnia della Vela” of Venice , of the same club as the “Moro di Venezia”.
The second Centomiglia, was won by the German “30mq” called Manjana belonging to the Bavarian skipper Martin Adolf. The “Centomiglia” becomes a world wide known event.
In the following years, the most peculiar, different and very fast boats took part in the competition of Lake Garda.
The competitors were won by Olympic boats such as the “5.50 Metre and the “Star” , the “Tornado”, fast boats such as the “Renjollen”and the oceanic boats such as the I° Class IOR “Guia” of Giorgio Falck which won in 1971.
Since the mid-seventies it has been the “Classe Libera” who has triumphed. This is a new class which started up with the “Centomiglia Style”.
The Italian boat “Cassiopea” belonging to Franco Nocivelli won four times, with an Italian crew while a German boat “Quartas “ skippered by Sepp Hoess, Flying Dutchman world champion, retorted.. While from Switzerland  the Olympic champion Noverraz sailed the Centomiglia.
In the eighties, the “super-leggero “ model., created by Bruce Farr was very popular on Lake Garda; the architect from New Zealand who is the one who has been going on designing the very fast sailing boats such as the one   that won the last “Round The World “.
Among the skippers whose names have been linked with the “Centomiglia  there are as well as the already mentioned  Falck (winner on two occasions) , the late –lamented President of the World Sailing Federation, Beppe Croce; the Swiss brothers Fehlmann, several times protagonists in the Round the World Race, Flavio Scala the 12 metre World Champion of the America’s Cup; the 
Olympic Champion  Fabio Albarelli, and the Italian sailors Mario Celon, Luca Santella and Giorgio Zuccoli ; the German Champion and the  World Vice-Champion of the Star class Werner Fritz; the 
Chairman of the Circolo Vela Gargnano, Andrea Damiani, four times winner, and  the three times winner Slovenian Dusan Puh. 
In 1996 Centomiglia was won by the “Asso99 one design “boat of Lievi and Larcher in 1997 it was won by the Libera class boat “Raffica” skippered by the Star World Champion Roberto Benamati. 
In 1998 and in 1999 Luca Valerio (Mumm 30 World Champion in 2001 – 2002)  In 2000, 2001 and 2002  Roberto Benamati wins the Centomiglia again with Joshi Entner on board of “Principessa” the new boat designed by Bruce Farr.
In 2001 and 2002 the Streamline boat designed by Judel and Vrolik and built  by Mader has won the Centomiglia in Group 3 the group of small boats.  
In 2003 the winner of the 53ª Centomiglia is “Clandesteam”, the yacht designed by the gardesano Umberto Felci and sailed by the skipper of the lake Oscar Tonoli and by the strategist Michele Ivaldi. In 2004 and 2005 the yacht Principessa, skippered by Joshi Entner, is the winner of the most famous Regatta of Europe. In 2006, 2007 and 2008 the winner is Clandesteam”, the yacht sailed by the skipper Carlo Fracassoli, member of Circolo Vela Gargnano,  and by the strategist Stefano Orlandi. In 2009 the winner is Full Pelt of the yacht owner Stephen Fein (helmsman Jo Richards) coming from Great Britain. In 2010 Wild Lady and its German helmsman Wolfgang Palm wins the first place, getting the President of the Republic’s trophy.
The Centomiglia is organised by Circolo Vela Gargnano, the sailing club which has taken part in the 32nd America’s Cup with the yacht +39.
In 2006 the “Centopeople” for all pleasure boats has born. Since 2006 the Club organises the “MultiCento”, a race which has the same course as the Centomiglia but reserved for the Multihulls.