Caffe Vittoria, Boston

Set on the North End's Hanover Street, in the very heart of Italian quarter, you'll find Caffe Vittoria, proudly claiming to be Boston's first Italian cafe since way back in 1929. And you know what? That claim actually holds up because this place exudes an old-world, funky, retro charm that'll transport you to rustic Italian towns and give those New England Starbucks a run for their money.

Small, metal-rimmed chairs and tables scattered about across the four floors of well-worn marble with three bars, glass display cabinets, and a treasure trove of vintage coffee machines and espresso makers, not to mention the prints, are good enough a reason to visit here, at least once, and is as close as it gets to a museum dedicated to the evolution of the modern cup of espresso.

Speaking of coffee, and especially the cappuccino, it is well worth your time, and will deliciously pair with the various Italian pastries they serve. Word on the street is that many celebrities and politicians swing by this North End hotspot for some of the best hot chocolate, cappuccino, and cannoli in Boston, maybe even in the whole U.S. of A!

Here's the kicker: all the bars at Caffe Vittoria serve up liquor, including some Italian Grappa that's definitely worth a shot... or two. And if you're feeling extra fancy, head to the basement where, back in 1995, the owners opened a cigar bar called Stanza dei Sigari – the last surviving smoking lounge in the city. The service is always outstanding, and the ambiance makes it a great place to kick back and relax.