5 Ways to Enjoy a Wine Advent Calendar This Holiday Season

The first time I bought myself a wine advent calendar, I had zero plan. I saw it in my cart, I saw the price, I thought "sure, why not," and I hit purchase somewhere around 11pm on a random Tuesday in October. I did not think about strategy. I did not think about pacing. I just assumed I would open a door every night like a reasonable adult and call it a day.

Some nights I forgot entirely. Some weeks I opened three doors in one sitting because I was "catching up." One year I accidentally gave my roommate the impression that this was a shared calendar, which led to an entire debate about whose turn it was to open door number 9. It was chaos, but it was delightful chaos, and it taught me something important: there is no one correct way to enjoy a Wine Advent Calendar, or even a Wine and Cocktail Advent Calendar if you like to mix it up. There are just a bunch of really good ways, and the fun part is picking the one (or two, or all five) that actually fits your life this December.

So if you already have your calendar sitting on the counter, or you are still deciding whether this is the year you finally buy one, here are five different ways to enjoy it. Steal one, mix and match, or try all five strategies (but be ready to drink a lot of wine!) This is a low stakes holiday tradition. There is no wrong answer here, only wine.

1. The Classic Countdown: One Wine a Day, December 1st Through Christmas

Let's start with the one everyone thinks of first, because honestly, it's the classic for a reason. This is the purest version of the ritual. You open door number one on December 1st, you open door number two on December 2nd, and so on, all the way through Christmas Eve (or Christmas Day, depending on how your calendar counts). One bottle, one night, no skipping ahead and peeking at what's behind door 15 even though we all know you've thought about it.

There is something genuinely soothing about this version. December has a way of turning into a total blur of errands, gift wrapping, group texts about whose house Christmas is happening at this year, and approximately four hundred group chats you now have to keep up with. A nightly pour gives you one small, guaranteed good moment in the middle of all of it. It does not matter if your day was a mess. It does not matter if you didn't finish your gift list or if your Christmas cards are still sitting in a stack, unaddressed, judging you quietly from the kitchen counter. You still get to open a little door, read the card, and taste something new.

A few tips if you're going the classic route:

• Pick a consistent time. Right after work, right before dinner, whatever actually fits your evening. The consistency is what turns this from "a thing I sometimes remember to do" into an actual tradition.
• Keep a little notes app going. Jot down what you liked, what surprised you, what you'd buy again. Trust me, by day 12 you will not remember what door 3 tasted like unless you write it down.
• Light a candle. Put on the playlist. Set the scene, even if the scene is just you, your couch, and a Hallmark movie you've already seen four times.

This one is ideal for the person who genuinely wants a nightly ritual and has the follow through to stick with it. If that's not quite your personality (no shame, same), keep reading, because there's an option for you too.

2. Pair It With a Food Advent Calendar, Because Wine Deserves a Snack

If you are the kind of person who thinks a glass of wine without something to nibble on is basically an unfinished sentence, this one is for you. Grab a Food Pairing Advent Calendar to enjoy alongside your wine calendar, and suddenly every single night turns into a tiny curated tasting menu instead of just a pour.

There is something about matching a bite to a sip that makes the whole ritual feel more intentional. Instead of drinking your wine while half watching TV (no judgment, we've all done it), you're actually thinking about what you're tasting. Does the cheese make the wine taste different? Does the wine change the way the chocolate hits? It turns a Tuesday night glass of wine into an actual tiny event, and honestly, in the middle of December, a tiny event is exactly what you need.

If you don't want to buy a second calendar, you can absolutely DIY this. Keep a running stash of things that pair well across the board, like:

• A good aged cheddar or gouda (works with reds and whites both)
• Dark chocolate, for the nights you land on something bold and fruity
• Marcona almonds or a simple nut mix
• Crackers and a soft cheese, for when you get a lighter white or sparkling

Either way, this version turns your wine advent calendar into a small nightly food and wine moment, and it makes the whole thing feel a little more special without a ton of extra effort.

3. Skip the Nightly Pour and Do Weekend Wine Flights Instead

Here is the honest truth: not everyone has the bandwidth for a nightly ritual in December, and that is completely fine. If your weeknights are already packed with holiday parties, work deadlines, and the general chaos of the season, you do not have to open a door every single night to enjoy this calendar.

Instead, save them up and do a proper wine flight on the weekend. Open six doors at once, line them up, and turn your Saturday afternoon or Sunday evening into an actual tasting session. This is honestly one of my favorite ways to do it, because it lets you slow down and really compare wines side by side instead of tasting them in isolation, one night at a time with days in between.

This version is also just a great excuse to play catch up if you've fallen behind, which, let's be honest, happens to basically everyone by week two. Nobody is grading you on whether you opened door 9 on the actual 9th. If you've got six unopened doors sitting there by Saturday, that's not a failure, that's a weekend tasting flight waiting to happen.

A few ways to make the weekend flight feel extra fun:

• Taste blind if you're feeling fancy. Cover the labels, guess the grape, then reveal. It's a fun little game if you've got a partner or friend doing it with you.
• Go from lightest to boldest. Taste your whites and lighter reds first, then move into anything richer or bolder, the same way you would at an actual tasting room.
• Take notes on your favorites. By the end of the month you'll have a real list of what to actually buy a full bottle of again.

This is the perfect approach if you're someone who likes a proper sit down tasting more than a quick weeknight sip, or if your weeks are just too packed to promise yourself a nightly ritual you probably won't keep.

4. Turn It Into a Long Distance Tasting Night With Friends or Family

This one might be my favorite of all five, honestly. If you've got family members scattered across different cities, or a best friend who moved away and you miss doing normal life stuff together, sync up your wine advent calendars and make December a shared thing instead of a solo one.

Here's how it works. Everyone buys the same calendar (or as close to the same lineup as you can manage). You pick a night, or a few nights a week, and everyone opens the same numbered door at the same time. Then you hop on a group chat, or a video call if you want to make it a whole thing, and compare notes. Did everyone taste the same thing? Did someone love the wine that someone else thought was just fine? It turns into this ongoing, low effort tradition that gives you a built in reason to check in with people you love, all December long.

What I love about this version is that it takes almost zero planning once you set it up. You don't need to coordinate a whole dinner party or find a date that works for six people's schedules. You just need everyone to have their calendar and their phone. Some nights the group chat is just a photo and a "this one's good" text. Other nights it turns into a full on debate about whether the pinot noir was actually better than the syrah. Either way, it's a genuinely sweet way to feel connected to people during a month that can otherwise feel like everyone is too busy to talk.

This is a great option if:

• You've got family members who live far away and don't see you until the actual holiday
• You and your best friend used to do wine nights in person and haven't found a replacement since one of you moved
• You just want an easy, no pressure reason to check in with people more than once during the busy season

5. Buy an Extra Calendar in November for a Friendsgiving Tasting Party

Okay, this one requires a little bit of planning ahead, but it might genuinely be the most fun option on this whole list. If you're hosting a Friendsgiving this year, open your wine advent calendar early, and use the mini bottles as tasting favors or conversation starters at your party.

Think about it. Instead of just setting out one or two bottles of wine for everyone to share, you set up a whole mini tasting bar. Guests can grab a mini bottle, try something new, and actually have something to talk about besides the usual "so, how's work." It turns your Friendsgiving into a real food and wine event instead of just a potluck with drinks on the side, and it gives people a reason to slow down and actually taste what they're drinking instead of just topping off a glass on autopilot.

A few ways to make this work at your party:

• Set up a little tasting station. Line up a handful of the mini bottles with small cards or labels so people know what they're trying.
• Let guests take one home. A mini bottle doubles as a cute, no cost party favor. Nobody is mad about a free mini wine on their way out the door.
• Pair it with your Thanksgiving spread. Mini bottles are a genuinely fun way to test what actually pairs well with turkey, stuffing, and whatever pie situation you've got going on.

Important note, and I cannot stress this enough: if you use your wine advent calendar for Friendsgiving in November, buy a second one for actual December. You do not want to get to December 1st with an empty calendar and a lot of regret. Ask me how I know.

You Don't Have to Pick Just One

Here's the thing I want you to walk away with. These five ways are not five separate boxes you have to choose between. Most people I know end up doing some combination of all of them across the month. Maybe you do the classic countdown on weeknights, save up a few doors for a weekend flight when life gets busy, and text your sister a photo of whatever you opened that night just because. Maybe you buy two calendars, one for a November Friendsgiving and one for your actual December countdown. Or maybe you go the Wine and Cocktail Advent Calendar route entirely and let each night decide for itself whether it is a wine night or a cocktail night. There is no wrong way to enjoy this, and honestly, that flexibility is part of what makes the format so much fun in the first place.

December moves fast no matter what you do. A wine advent calendar, in whatever form you enjoy it, is just a small built in excuse to slow down for a few minutes, taste something new, and actually notice the season happening around you instead of letting it blur by in a haze of gift wrap and group chats.

Frequently Asked Questions About Enjoying Your Wine Advent Calendar

Do I have to open a door every single day?

Not at all. Plenty of people fall behind and catch up on weekends, and there's no rule that says you have to open exactly one per day. The calendar is meant to be a fun ritual, not a chore with a strict schedule.

What's the best way to enjoy a wine advent calendar with other people?

Syncing up with friends or family, even remotely, is one of the easiest ways to make it a shared experience. Everyone opens the same numbered door on the same night and compares notes over text or video call.

Can I use a wine advent calendar for a party instead of a nightly countdown?

Absolutely. Mini bottles work great as tasting favors or a mini tasting bar for a Friendsgiving or holiday party. Just remember to grab a second calendar if you still want to do your own countdown in December.

What should I pair with my wine advent calendar?

A Food Pairing Advent Calendar is a fun option if you want a curated bite to go with every pour, but a simple rotating snack stash of cheese, chocolate, nuts, and crackers works just as well.

Is it okay to skip around instead of opening the doors in order?

Most calendars are sequenced with intention, building from lighter styles toward bolder ones as the month goes on, so opening them in order tends to give you the best experience. That said, this is your calendar and your December, so there's no wine police coming to check.

However you decide to enjoy yours this year, the goal is the same: a little more joy, a little more slowing down, and a lot more good wine between now and Christmas. Browse our Wine Advent Calendars, check out the Wine and Cocktail Advent Calendar if you want a little of both, or grab a Food Pairing Advent Calendar to go alongside it, and start counting down.