You Know What Breaks My Heart Every October?
Watching wineries hustle so hard during the holidays… only to leave money on the table. And it’s not because the wine isn’t good. It’s because the planning went sideways.
Today we’re talking about the three planning pitfalls that quietly tank OND (October, November, December) sales for wineries.
Avoid these, and you’ll sell more wine with less chaos, and maybe even get to enjoy your own holiday party this year.
Pitfall #1: Being Reactive Instead of Proactive
Too many wineries build promotions around what’s left in the warehouse instead of what’s strategic to move.
That’s reactive marketing, and it leads to rushed campaigns, thin margins, and frustrated teams.
Instead, pick your hero wines early in the season. Decide what deserves the spotlight and plan your campaigns around those SKUs. This simple shift keeps you intentional with your inventory and protects your profit margin. (Early means early. Here’s why smart wineries start holiday email planning in June.)
Pro Tip: Start with your core DTC products and build supporting offers around them. Example: lead with your flagship Pinot Noir and bundle it with seasonal shipping perks or gift packaging.
Pitfall #2: Not Having Image Assets Ready
This one hurts, because you can have the best copy and the strongest offer, but a blurry bottleshot can tank the whole campaign.
Your audience is seeing perfectly polished visuals from Amazon, Nordstrom, and every other brand in their inbox. Your winery emails have to look as good as your wine tastes.
Make sure you’ve got:
- Clean, professional bottleshots of your hero SKUs
- A few lifestyle or tasting room photos that feel festive and current
- Crops and aspect ratios that work for both email and social
Quick Win: Schedule one photo session before OND starts. Get 10 to 15 assets you can reuse across every campaign.
Pitfall #3: Planning in Silos
Here’s the chaos culprit I see every year: email says one thing, SMS says another, the tasting room has their own special, and telesales is making up a new script every day.
That’s confusing for customers, and exhausting for your staff.
Instead, bring your team together around one unified campaign calendar.
Each channel (email, SMS, tasting room, telesales, social) should amplify the same offers, with slightly adjusted messages for each audience. If email and SMS in particular aren’t talking to each other yet, start with email and SMS marketing for wineries.
Mavens Mantra: Cohesive campaigns convert. Coordinated teams crush.
Bonus Pitfalls (Quick Fixes)
If you’re nodding along thinking, “We’ve done all of those,” don’t panic. You can course-correct quickly.
Here’s your mini checklist:
- Map campaigns to shipping cut-offs to avoid expedited shipping costs.
- Don’t overstuff your offers. Lead with one hero product at a time.
- Have a backup plan in case a SKU sells out or weather delays shipping.
Small adjustments now = smoother campaigns and stronger sales later.
And once the plan is solid, make sure the emails themselves aren’t undoing it. We covered the scary email tactics killing winery holiday sales separately.
Plan to Win This Holiday Season
If your inbox is already filling up with “holiday offer” emails, that’s your cue. It’s go time.
You don’t have to wing it. You just need a clear plan, strong visuals, and a little coordination between channels.
Start with the free Winery Email Marketing Playbook, your roadmap to writing and sending winery emails that actually convert.
Then, if you want the monthly strategy, templates, and campaigns built specifically for wineries, that’s Mavens On Demand.
Less scrambling, more sipping. That’s the OND spirit.
Winery Holiday Marketing FAQs
When should a winery start planning holiday campaigns?
June or July for the plan, September at the latest for the assets. Picking hero wines, reserving inventory, and booking a photo session all need to happen before October, or you’re back to building promotions around whatever’s left in the warehouse.
How many hero wines should a winery promote during OND?
Two or three, one at a time. Each campaign leads with a single hero SKU and builds supporting offers (gift packaging, shipping perks, bundles) around it. Spreading attention across the whole catalog is how offers get overstuffed and margins get thin.
What image assets does a winery need before the holidays?
Clean bottleshots of every hero SKU, a handful of festive lifestyle or tasting room photos, and crops that work in both email and social. One photo session before OND, 10 to 15 usable assets, and you’re covered for the season.
How do I keep email, SMS, and the tasting room on the same page?
One shared campaign calendar with the same offers on every channel, adjusted in tone for each audience. Email tells the story, SMS reminds, the tasting room and telesales reinforce. When the channels disagree, customers hesitate and staff burn out.
