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Planning Your Winery Holiday Sales Strategy: Beyond the Tasting Room

The peak winery holiday sales season, OND, is nearly upon us. OND, which stands for October, November, and December, is the three months responsible for roughly 30 percent of a winery’s annual sales and the highest DTC sales of the year. Are you ready? Right now, during harvest, tasting rooms are full. That traffic drops in November and December as the weather turns and calendars fill with holiday plans. Wineries that win next quarter build a winery holiday sales strategy while harvest is still happening, not after the rush ends. This post lays out five pillars: social media, email marketing, wine club and allocations, gift-giving, and personal holiday buying to maximize your end of year sales.

A free, downloadable OND Sales Prep Checklist walks through each pillar below in a one-page, build-it-yourself format, and a companion working sheet helps you map out your own posts and emails. Both live with the rest of my free resources on the Planning Tools page. Grab them before you keep reading, use them this year, and keep them for years to come.

The Story You’re Telling, From Harvest To The Holiday Table

A winery holiday sales strategy works as a story, not a string of unrelated posts. Every strong OND campaign has a beginning and an end, and the shift between them needs to happen earlier than most wineries assume.

Harvest and winemaking open the story, because that’s genuinely what’s happening right now. This content is current, compelling, and easy for your audience to connect with. But the story can’t stay there. Shipping lead times force an early messaging shift: gift and holiday orders need to ship by early-to-mid December, so the messaging that drives those orders has to start well before that.

The story closes on someone’s table: wine opened at Thanksgiving, poured at Christmas, uncorked at midnight on New Year’s. That payoff is what you’re building toward from the first harvest post.

Pillar One: Social Media As A Story, Not A Single Post

Your OND social media shouldn’t carry your entire content calendar, but it should be the primary theme running through it. A weekly-to-biweekly cadence carries the arc without overwhelming everything else you post.

Structure each post around the same story: harvest and winemaking content early, then gifting and holiday-purchase content once harvest wraps. If you keep a blog, use the blog post to set this structure, then let biweekly or bimonthly posts build quickly toward the story’s end: gift-giving and enjoying your wine at the holiday table. The working sheet in the OND Download gives you a place to map out each post by theme, date, and platform, so you’re not starting from a blank page.

Pillar Two: Email Marketing That Targets

Start with a strategic decision. Which wines will you focus on this quarter, and why? Choose wines that pair well for gifting or food, wines sitting in surplus, or wines you need to move off the shelf to make room for the next vintage. Whatever the reason, targeted messaging moves the wine, not a discount. Selling quickly and strategically, at retail price, or at wine club price for members, protects your margin and your brand.

Once you’ve picked the wines, match each one to the right list segment. Past buyers of that wine, buyers of similar wines, and customers with a history of larger end-of-year purchases each deserve their own message. This isn’t complexity for its own sake. It’s telling the right people “we thought of you” .

Pillar Three: Wine Club, Shipments, AND Allocations

None of these decisions stand alone. Your wine club shipment date is fixed, so everything else moves around it.

Here’s the ideal sequence: the wine club shipment lands early enough for members to taste the wines before the holidays arrive. From there, targeted holiday and gifting emails upsell those same members on wines, or the target wine, that they’ve already received, whether from the current shipment or the one before it. They’ve tasted it already. You build on that.

If your timing doesn’t line up that way, you have options. Upsell the wines in the coming shipment, building on the idea that these wines are good enough that members should buy more. Or target non-members with emails built around your last shipment’s wines, wines your members already tasted and already have in hand, and use those campaigns to convert them onto the wine club.

None of this works if the wine itself isn’t ready to ship. Allocations planning is the operational work behind the marketing: confirm inventory for the wines you’re pushing, position that wine at your shipper, resolve compliance issues ahead of time, and finalize packaging and inserts. Handle this early. Wine sitting unshipped, because it never reached the shipper or nobody properly logged it, turns a strong marketing push into a broken promise.

Pillar Four: Gift-Giving With Creativity

Gifting is where wineries get to experiment. Build multi-wine packages that feel like an actual gift when the box opens, not just bottles in a box. Partner with local non-wine vendors, glassware makers, artisan food producers, anyone whose product pairs naturally with yours, and give customers a reason to buy both. Give people a way to gift the relationship itself, too: a one-year wine club membership makes a far better gift than a single bottle, and it brings you a new member.

Pillar Five: Remind Customers To Treat Themselves

Everything above targets gift-giving. This last piece targets customers buying for themselves. People hosting Thanksgiving, attending a holiday party, or ringing in New Year’s deserve a reminder that they can treat themselves too.

This is the one message in your winery holiday sales strategy that goes out to everyone: the full wine club, full email list, every social channel, with no segmentation. Whether the tone is a simple “you deserve it too,” a reflective “this year’s been a lot, be good to yourself,” or “you give so much to others, you can give to yourself too,” the point stays the same. It closes the story you started with harvest, bringing it back to the person reading the message.

The Plan, Together: Your Winery Holiday Sales Strategy

These five pillars aren’t five separate projects. Together, they form one winery holiday sales strategy for OND. Start with the three or four key wines you want to sell this season. Your email, themes tie back to these wines and those in your wine club shipments. Your social media posts, and your blog posts support these emails. Then your allocations work finishes early before any of it goes out. Treat OND as one connected plan, not five separate ones.

The OND Sales Prep Checklist and working sheet pull all five pillars onto tools you can build out for your own winery. They are a free downloads on the Planning Tools page, alongside my other resources for winery owners. If you’d like help turning any of this into a plan specific to your business, that’s exactly the kind of work I do with winery clients.

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