Cipresso started his winemaking career in Montalcino, where he worked with Case Basse, Poggio Antico and Ciacci Piccolomini d’Aragona. From there, he founded “Winemaking”, assisting more than thirty wine companies throughout the Italian territory. Past collaborations include the prestigious Achaval-Ferrer Winery, Matervini in Argentina, and Bueno Bellavista in Brasil. Recently he started a new collaboration with Vinos de la Luz in Argentina and Spain, fulfilling his dream of working with the Tempranillo variety. He went on to found La Fiorita Winery, located in the heart of Montalcino as well as become the owner of a Brunello vineyard, near his Resort of Poggio al Sole. He also founded The Winecircus project, a wine cellar and laboratory, dedicated to the research of vine activity.

His fine wines have won many awards. In 2011, Robert Parker awarded Cipresso’s five wines with one 99/100, three 98/100 and one 97/100. During 2012, his Brunello di Montalcino Riserva 2006 La Fiorita received a 95/100 Wine Spectator rating, and was listed as one of the Best 50 Wines in Italy during the Best Italian Wines Awards 2012. In addition it received the Gold Medal at the “Merano Wine Festival 2012”. In 2015, Wine Spectator honored his Brunello di Montalcino 2010 La Fiorita with a 95/100 rating. Personal highlights include: creating a special Cuvee for the Pope John Paul II during the 2000 Jubilee; receiving the award for Best Italian Oenologist during the “Wine Oscars of 2006” and being named “Man of the Year” in 2008 by Men’s Health Magazine, Food category. In April 2010 he met Italian Republic President, Giorgio Napolitano, and was asked by “Città Del Vino” to develop a special wine for the 150th Anniversary of Italian Unification.