An Insider's Guide to Tuscany

Tuscany is all about slow travel, with rolling countryside, hilltop towns, and long lunches. In Siena, Montepulciano, and Montalcino, you’ll find medieval streets, world-class wine, and a pace that encourages wandering. Neighboring Umbria shares the same scenic charm but feels a bit more under-the-radar, with towns like Assisi and Spello offering fewer crowds and plenty of character. 

This region appeals to couples, food and wine travelers, or anyone craving the countryside over city buzz. Expect days filled with wine tastings, farm-to-table meals, and drives through postcard-worthy landscapes. Read on to find out where to stay, eat, and explore across the smaller towns in Tuscany.