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Creating a Holiday Promotions Calendar That Drives Results

Your Step-by-Step Guide to Strategic Seasonal Marketing for Wineries

The holiday season presents one of the most lucrative opportunities for wineries to boost revenue, deepen customer engagement, and elevate brand visibility. But to capture the full potential of Q4, you need more than just festive packaging and last-minute email blasts—you need a strategic, data-driven promotions calendar that aligns timing, messaging, and offers with peak shopping behavior.

Here’s how to build a holiday promotions calendar that doesn’t just check boxes—but drives real results.

Step 1: Define Your Holiday Goals

Before you start plugging dates into a calendar, get crystal clear on your objectives. Each winery’s priorities will differ, but your calendar should support goals like:

  • Increasing DTC revenue through online and tasting room sales

  • Growing or retaining wine club memberships

  • Driving traffic to your website or physical location

  • Clearing inventory of specific SKUs before year-end

  • Engaging gift buyers and corporate clients

Once you know what success looks like, you can reverse-engineer your promotions to support those outcomes.

Step 2: Identify Key Holiday Milestones

Plotting out major retail and wine industry dates is essential. Here's a breakdown of high-impact dates to build around:

  • Early November: Pre-launch teaser emails & wishlist building

  • Veterans Day (Nov 11): Soft launch for email subscribers or loyalty members

  • Thanksgiving Week: Prime window for traffic & gifting

  • Black Friday (Nov 29): Deepest discounts or limited offers

  • Small Business Saturday (Nov 30): Focus on local and artisanal storytelling

  • Cyber Monday (Dec 2): DTC-specific bundles or flash sales

  • Holiday Shipping Cutoffs: Include ground and expedited deadlines

  • Christmas Eve (Dec 24): Promote local pickup or e-gift cards

  • New Year’s Eve (Dec 31): Sparkling features or celebratory bundles

These anchor points help ensure your campaigns ride the wave of consumer momentum, rather than getting lost in inbox noise.

Step 3: Map Your Campaign Cadence

Now that you’ve pinpointed the dates, assign each one a campaign type and marketing theme. Structure is key—here’s an example timeline:

Date Theme Tactic
Nov 1–7 Early Access / Wishlist Email + Social Teasers
Nov 8–11 Loyalty Appreciation / Veterans Day Targeted Email + SMS
Nov 15–21 Bundle Launch Email + Web Banners + POS Scripts
Nov 25–Dec 2 Thanksgiving–Cyber Monday Multi-touch Campaign (Email, SMS, Ads)
Dec 3–10 Gift Guide Push Blog + Social Ads + Influencers
Dec 11–17 Shipping Countdown Daily Reminders + Scarcity Messaging
Dec 18–24 Last-Minute Gifting E-Gift Cards + Pickup Only Messaging
Dec 26–31 Cheers to the New Year Sparkling Spotlight + Cross-sell Club
Each touchpoint should feel fresh and valuable, with clear calls to action. Use urgency, exclusivity, or convenience to prompt decision-making.
 

Step 4: Choose the Right Channels

Not all platforms are equal when it comes to converting holiday customers. Your best bet? A multichannel approach that matches message to medium:

  • Email Marketing: Your highest-ROI tool. Use it to build anticipation, announce drops, and nurture segmented audiences (e.g., club members, high-value buyers, gift givers).

  • Social Media: Ideal for real-time engagement, storytelling, and remarketing. Reels, countdowns, and behind-the-scenes content work well.

  • SMS: Perfect for urgency-based messaging—think limited-time offers, shipping deadlines, or VIP early access.

  • Website & E-commerce: Feature holiday landing pages, homepage banners, and pop-ups. Make it easy to gift, shop by price, and filter by shipping eligibility.

  • Tasting Room: Equip staff with offer scripts, signage, and QR codes for easy opt-ins and gift sales.

Keep your branding consistent across all channels and make the customer journey seamless from first touch to checkout.

Step 5: Align Promotions with Inventory and Fulfillment

Holiday success is as much about logistics as it is about marketing. To avoid missed opportunities (or overselling), work closely with your operations team to:

  • Forecast which wines will be included in bundles or discounts

  • Ensure packaging and inserts are ready in advance

  • Build timelines around your warehouse or fulfillment partner’s shipping cutoffs

  • Factor in potential delays for custom labels or gift boxes

Also, consider your staff—make sure they’re trained, scheduled, and equipped to handle increased demand both online and onsite.

Step 6: Layer in Automation & A/B Testing

Let technology do the heavy lifting. Use:

  • Automated Email Flows: Abandoned cart reminders, post-purchase thank-yous, and win-back emails

  • Segmented Lists: Differentiate messaging for new vs. returning buyers, gift givers vs. wine club prospects

  • A/B Testing: Test subject lines, call-to-actions, or offer types (free shipping vs. % off) to optimize results in real-time

Even small refinements can yield significant gains in open rates, click-throughs, and conversions.

Step 7: Measure and Iterate

After the New Year’s toast has been poured, dig into your data:

  • What was your best-performing campaign and why?

  • Which offers led to the highest average order value?

  • Where did most conversions come from—email, SMS, ads, tasting room?

  • What products under- or over-performed?

Use these insights to refine your approach for next year, and consider running a post-holiday campaign (think “New Year, New Wines”) to maintain momentum.

Final Thoughts

A well-crafted holiday promotions calendar doesn’t just drive seasonal revenue—it builds long-term loyalty, grows your customer base, and showcases your brand at its most generous and joyful. By aligning messaging with timing, leveraging the right channels, and backing it all with solid logistics, you’ll turn the holiday rush into meaningful results.

Need help getting started?
Download our Holiday Promotion Planning Template to map out your winery’s campaigns, deadlines, and marketing assets—all in one place.

Let’s make this your most profitable and purposeful holiday season yet.
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