The six weeks between Thanksgiving and New Year’s Eve aren’t one sales push — they’re several different buying occasions layered on top of each other, often hitting the same customer list in the same week. This guide breaks down how wineries and wine retailers can plan, staff, and message each window separately, starting earlier than most teams expect.

Every holiday order falls into one of three buyer intents: someone buying wine to drink on the occasion itself (timing and pairing matter most), someone shopping a deal (price matters most), or someone buying a gift on a budget (a clear pre-built option at their price point matters most). Send all three the same generic discount email and you lose all three. This guide walks through how to split — and sequence — your messaging so each buyer gets the version of the pitch that actually moves them.

What’s Inside

(Each window below gets a full messaging and timing breakdown in the guide — this is the overview.)

October — Prime the Reorder Cycle

An early push built around near-term consumption, designed to set up a natural November and December reorder once customers drink through what they bought.

Thanksgiving Week — The Family Table Moment

Thanksgiving is often the largest audience of non-customers a winery or retailer will reach all year. The guide covers how to think about who’s actually drinking the wine — and how to turn that table into a brand-expansion opportunity.

Black Friday & Cyber Week — The Deal-Seekers

A distinct audience from Thanksgiving, shopping on price and gifting, not pairing. The guide covers how to keep this messaging separate from the pairing-led Thanksgiving push.

New Year’s Eve — Win the Sparkling Sale Early

Most people buy bubbles once per season. Lose that purchase moment to a competitor and you don’t just lose a sale later — you lose it entirely. The guide covers why the sparkling push should start earlier than most teams plan for.

December Gifting Rush — Make Buying Easy

The highest-volume window of the season, and the one where ease of purchase — especially for corporate and gift buyers — matters more than discounting.

January — The Restock (and the Cellar Play)

The month most sellers go quiet is often the biggest missed opportunity of the season: a restock month for regular drinkers, and — for wineries navigating Dry January — a window to move scarce, age-worthy wines to buyers who don’t need to drink them yet.

Who This Guide Is For

Built for winery DTC and tasting room teams, and for wine retailers managing multi-channel holiday sales — anyone planning holiday marketing calendars, staffing peak-season fulfillment, or setting corporate and gift-order processes.

What You’ll Walk Away With

• A framework for planning holiday selling around buyer intent, not just the calendar.
• A week-by-week playbook for October through January, including specific messaging angles for each window
• A worksheet to rate what matters most for your business and build your own holiday selling calendar.
• Guidance on corporate and bulk gifting, gift-ready packaging and pricing, and post-holiday retention