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The Best Wine Advent Calendars to Toast the Holiday Season

The perfect way to wine down.

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They call the Advent season—the lead-up to Christmas Day—the happiest time of the year for a reason. The months-long celebratory season gives you an open invitation to revel by decking the halls, decorating the tree, singing carols, bingeing holiday movies, and wearing nothing but flannel pajamas as you sit fireside with a cup of hot cocoa.

And now there's an excuse to add a new holiday tradition to your list. But this one is only for the adults in the family. It calls for swapping out that hot cocoa for lots and lots of vino, brought to you by a twist on the traditional advent calendars filled with chocolates.

Like other unique countdown calendars filled with skincare and beauty products, wine advent calendars give you something special to look forward to every day during Advent. And let's be honest: Does anything sound better than rounding out the hustle and bustle of the day with a little night cap, courtesy of what's behind door number...two?

Let us help serve you. We searched high and low, cherry picking some of the best wine advent calendars to gift friends and family—or, perhaps more likely, yourself. From 24-day calendars to shorter 12-day options, these festive advent boxes are packed with reds, whites, prosecco, rosé, sparkling wine, and more. Some doors even open to reveal full-size bottles of your favorite varietal. It's bound to be a very merry season, indeed.

1
Best Wine Club-Sponsored

Wall Street Journal Wine Advent Calendar

Wine Advent Calendar
Credit: Wall Street Journal

From one of the most popular wine clubs comes an advent calendar you won't want to miss. The gingerbread house-inspired box is filled with 24 quarter-bottles—that's one very generous glass—to enjoy each day leading up to Christmas.

2
Best Variety

Reindeer Wine Advent Calendar

Reindeer Wine Advent Calendar
Credit: World Market

Take a trip to France this December with this reindeer-decorated festive wine advent calendar box that comes with a selection of 24 mini French wines—including sparkling, white, red and rosé. Just note: The box is only available for purchase in select World Market stores. (You might want to call ahead!)

3
Best Affordable

Sip & Savor Snowman Sweater Wine Advent Calendar 24 Pack

Snowman Sweater Wine Advent Calendar 24 Pack
Credit: Sip & Savor

It's the most wine-derful time of the year, indeed—especially with this advent calendar waiting for you each day. The variety pack is filled with 24 mini bottles of wine (you'll get one generous pour out of each) in just about every varietal you can think of.

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4
Best Tasting Experience

Vinebox 12 Nights of Wine Wonderland Box

12 Nights of Wine Wonderland Box
Credit: Vinebox

This seasonally-inspired box is filled with 12 glasses of world-class wine: four whites, two rosés, and six reds—all handpicked by sommeliers. Want a little bit more? You can always upgrade to the 24-night box.

5
Best Sparkling

Vintner's Choice 12 Days of Bubbles Advent Calendar

Vintner's Choice 12 Days of Bubbles Advent Calendar
Credit: Harry and David

Your friend or family member's holiday season is virtually guaranteed to be popping, thanks to this sparkling wine advent calendar. Inside each drawer, they'll find a mini bottle of brut cuvée, brut rosé, moscato spumante, or pink moscato.

6
Best Affordable

Most Wonderful Wine Advent Calendar 2022

Most Wonderful Wine Advent Calendar 2022
Now 13% Off
Credit: Total Wine

If you're satisfied with a few sips each day, you'll love the variety this 24-bottle advent calendar features. Each day you'll find a carefully-selected varietal from all around the world.

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7
Best Packaging

24 Nights of Wine

24 Nights of Wine
Now 17% Off
Credit: In Good Taste

Any person enjoying this wine advent calendar is sure to have a happier holiday season. It contains 24 mini bottles of wine—red, white, and rosé—in glass bottles that are almost too pretty to crack open.

8
Best Canned Wines Advent

My Kindness Advent Calendar

My Kindness Advent Calendar

Treat the nicest people on your list (or, hey, you could totally treat yourself!) to a little pre-holiday present: 24 cans of fine wine all wrapped up in one pretty package.

9
Best Half-Bottles

Vintage Wine Estates 12 Bottles of Wine Advent Calendar

12 Bottles of Wine Advent Calendar
Credit: QVC

Favor pinot? Or maybe merlot or moscato? When you can't settle on a favorite, this 12-bottle advent calendar is the way to go, since you'll get a wide array of varietals (in half-bottles!) hand-selected from Vintage Wine Estates.

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10
Best Reusable Advent Calendar

PromiDesign Advent Calendar Wine Bottle Holder Wooden Christmas Tree

Advent Calendar Wine Bottle Holder Wooden Christmas Tree
Now 30% Off
Credit: Etsy

Wine advent calendars tend to sell out quickly, so if your fingers aren't quite speedy enough to catch the one you want or you simply prefer to curate your own selection, this beautiful wooden stand will do just the trick. It fits 24 small bottles of wine—and makes the perfect centerpiece for the bar at any holiday party.

11
Best Wine Spritzers

Usual Chrismukkah Wine Collection

Chrismukkah Wine Collection

This special Chrismukkah collection features 12 wines, and 8 Spritzes, making sure your family, friends, and yourself all have a very festive event this holiday season.

12
Best Assortment

Maker Canned Wine Advent Calendar

Canned Wine Advent Calendar
Now 14% Off
Credit: Maker

Yes, you can enjoy some vino on the go—with this curated collection of premium canned wine. Not only are of the the 12 cans (think: Sonoma County Sparkling Sauvignon Blanc, single-vineyard Alexander Valley Cabernet) produced by different, award-winning female and minority-led wineries, but they also contain one-third of a bottle, making it the perfect single-serving pour.

Headshot of Brigitt Earley
Brigitt Earley
Contributing Writer

Brigitt is a writer, editor and craft stylist with nearly 15 years of experience. She specializes in lifestyle topics, including home, health, parenting, beauty, style, food, entertaining, travel and weddings. She has written for Glamour, People, Good Housekeeping, Women's Health, Real Simple, Martha Stewart, Apartment Therapy, The Spruce, and more.

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