Why you should go: Escape to Italy with a group of friends for a quintessential Tuscan experience, the highlight of which is a private, expert-led truffle hunt where you’ll learn why they're such prized — and pricey — gems. This 5-night adventure also includes a multi-course dinner featuring freshly harvested truffles, allowing you to savor these culinary treasures yourself. And, a trip to one of the world's most renowned wine regions wouldn't be complete without a tasting and cellar tour at a 700-year-old winery. Yes, that's included, too.

What’s the big deal? For $1479, four guests will spend five nights on a centuries-old estate in a fully-equipped two-bedroom apartment. You have the option to go as soon as December or plan a trip for next spring or fall. Don’t have a group of four? No problem — two travelers can enjoy everything mentioned above for $999.