I wandered through 12 cities in Italy in high school on a very memorable school trip, but have yet to go back. It’s on the top of my list to revisit that gorgeous country as an adult, particularly Tuscany. And if I had won the mega-millions I would be sure to book myself a nice little villa at Castiglion del Bosco. A grand estate renovated by the Ferragamo family (of the famous fashion house) it appears sprawling, lush and perfectly amazing. Of course the style of the interiors is insanely gorgeous- using a mix of natural materials like rustic wood and stone but also luxurious fabrics and furniture of a more tailored measure. But what’s NOT to like about this kind of destination for vacation? Pasta, wine, sun, spa, golf, more wine and then for good measure, some more wine.