There are many, many Italian restaurants in Chelsea to choose from. There’s the old school ones, the very expensive ones, and then the ones you shouldn’t miss. Il Trillo is kind of a combination of all three. It’s been open for over 30 years, has a slightly dated but endearing feel, and can be expensive. But doesn’t have to be. Most of their handmade pastas come in half portions, so the best game plan is to swing by with a group, order several and make your way through the pretty epic wine list. Thanks to the garden out back that’s open all year round, this place is also prime date night material.