Creating a Holiday Promotions Calendar | Plan, Execute & Maximize Winery Sales

Timing Is Everything
The difference between a good holiday season and a great one often comes down to timing — and timing starts with a plan. Wineries that launch campaigns before mid-November see up to 18% higher average order value (AOV) than those that start later.

A clear promotions calendar turns reactive marketing into a proactive roadmap that guides your team from November through year-end. It’s your playbook for consistency, coordination, and customer delight.

For a complete foundation in forecasting and planning, revisit How to Prep Your Winery for Holiday Sales. 

A structured campaign calendar keeps every department aligned, from marketing and fulfillment to tasting room staff and customer support. 

Benefits of a Holiday Promotions Calendar: 

• Eliminates last-minute chaos and duplicated efforts 

• Ensures every message reinforces your seasonal brand theme 

• Allows better coordination between email, social, and club campaigns 

• Helps track performance by channel and timing 

Use the Winery Holiday Operations Planner to organize your holiday timelines, promotions, and key milestones. 

Plan your campaigns in phases that align with customer behavior and fulfillment realities. 

Recommended Timeline: 

• Early November: Announce pre-holiday perks for club members. 

• Mid-November: Launch general promotions and referral offers. 

• Thanksgiving Week: Emphasize shipping deadlines and “last call” bundles. 

• Early December: Promote digital gift cards and local pickup options. 

• Mid–Late December: Focus on in-person sales and thank-you campaigns. 

For deeper insights into club strategies that complement each phase, see Top Tactics for Maximizing Club Revenue. 

Download the Holiday Readiness Playbook for DTC Wineries for a complete seasonal strategy from planning to post-holiday follow-up. 

Consistency drives recognition, your promotions should reinforce a clear, emotional message throughout the season. 

How to Develop Compelling Campaigns: 

• Identify your unifying theme (e.g., “Share the Season,” “Gifts Worth Gathering For”). 

• Create tiered offers that appeal to different buyer types. 

• Bundle products for gifting convenience (three-pack, sampler, or limited holiday edition). 

• Use storytelling across all platforms to highlight your winery’s craftsmanship and people. 

Data point: Wineries that run multi-channel campaigns (email + social + in-person) see 22% higher conversion rates (WineBusiness Analytics 2024). 

For customer-facing tone and communication examples, check out Holiday Customer Service Tips. 

Your best campaign ideas only succeed if fulfillment, support, and staffing are in sync. 

Best Practices for Cross-Team Alignment: 

• Share the promotions calendar with all departments. 

• Include cutoff dates, marketing themes, and expected order volumes. 

• Hold weekly 15-minute check-ins to review campaign performance and inventory. 

• Use OrderPort’s unified platform to track orders, promotions, and customer engagement in real time. 

Coordinate every detail — from marketing to fulfillment — with the Winery Holiday Operations Planner. 

Your promotions calendar isn’t static; it’s a living strategy. 
Tracking performance helps you identify what worked and what needs to shift for next year. 

Metrics to Track: 

• Campaign open and click-through rates 

• Conversion rates by channel 

• Revenue by promotion type 

• Gift card and club referral uptake 

Use OrderPort’s analytics dashboard to evaluate results weekly, then compile insights in January for your 2026 planning cycle. 

For forecasting and post-holiday review strategies, revisit How to Prep Your Winery for Holiday Sales. 

The holidays are too important to leave to last-minute marketing. 
A thoughtful promotions calendar keeps your team aligned, your campaigns consistent, and your customers delighted, all while driving stronger results. 

Plan ahead, coordinate with purpose, and execute with confidence. 

Start building your promotions calendar with the Holiday Readiness Playbook for DTC Wineries — your roadmap to a profitable, stress-free season. 

Frequently Asked Questions (Holiday Promotions Planning) 

Q1: When should wineries start planning their holiday promotions? 
A: Begin planning in early October to align inventory, messaging, and staffing before peak sales. 

Q2: What’s the best time to launch holiday promotions? 
A: The first or second week of November, data shows earlier campaigns generate higher AOV and repeat engagement. 

Q3: How often should wineries communicate promotions to customers? 
A: Send one major campaign per week during November and early December, supported by smaller reminders and social posts. 

Q4: How does OrderPort support holiday campaign planning? 
A: It connects marketing, ecommerce, and club data in one platform, helping teams coordinate, track, and optimize campaigns efficiently.