Why you should stay: If you’re going to Tuscany, why not opt for a luxurious castle in one of Italy's top wine regions? The 1000-year-old Castello di Velona in Montalcino is surrounded by organic vineyards and olive groves. It also features volcanic hot springs that feed its five indoor and outdoor pools.

What’s the big deal? For $1399 for two people, your two-night stay comes with $545 of perks. Think daily breakfast, a two-course lunch, a wine tasting and more.