Tuscany is one of Italy’s most sought-after regions, known for its exquisite wine, charming hilltop towns, breathtaking rolling hills, and meticulously curated vineyards. That said, the area is huge, so it can be overwhelming to know where to begin. After 15 years of visiting this beautiful region, I’m excited to share my insights on where to stay—and where to avoid—during your Tuscan adventure.