The 10 Best Boozy Advent Calendars to Get This Holiday Season — Fri, Nov 21, 2025

Let’s be clear: Advent calendars aren’t just for kids tearing into cardboard for chocolate anymore. It’s 2025, and the doors should pour. We’re talking mini bottles of whiskey, sippable flights of wine, pocket-size gins, even craft-beer lineups that turn December into a very merry tasting menu. It’s the grown-up countdown you actually look forward to: one tiny surprise, one excellent nightcap, 24 times over.

There are a lot of boozy calendars out there—some great, some gimmicky—so we narrowed the field to the 10 we’d actually spend our own money on. These are our personal favorites, the ones that keep landing at Esquire happy hours and disappearing fast. Expect a smart mix of styles and spirits, from whiskey to wine to beer and beyond, with options for beginners, obsessives, and anyone who believes holiday cheer should arrive in 50ml bottles. Bottoms up.

Looking for something strong? I've never actually seen Moonshine except in the Nashville airport, but you can try 12 bold flavors of the infamous spirit made in Tennessee from Ole Smoky with this fun holiday countdown. Maybe you'll love one of the brand's classics like Apple Pie or Banana Pudding. Maybe you'll prefer one of its more seasonal, festive flavors like Butter Pecan. Won't know until you try!

Source: Esquire (Bellamy Richardson), November 2025