My favorite thing about engagement sessions is they get to be a little slice of life so is there anything better than a destination engagement session which can perfectly capture the memories of an incredible trip exploring the Tuscan countryside? I spent a lovely Fall weekend photographing the incredibly sweet (and fashionable) Tom and Tim at Il Borro, a 1000-year-old castle estate and medieval village in Tuscany owned by the Ferragamo family. Tim, a former bronze medalist Olympic Ice Skater, was celebrating his master’s degree from NYU and of course their recent engagement. Tom popped the question at the historic Chanler in Newport, RI, where the couple will say their I Do’s next year. The trip was spent wine tasting, sight-seeing in Cinque Terre, truffle hunting, shopping and eating way too much incredible Italian food. Minus a little rain in Cinque Terre we lucked out with a perfectly gorgeous Fall weekend, getting to enjoy the bright red leaves crawling up the wine caves and and the perfect little breeze as we explored the medieval town.