
Black Friday is November 27, and Cyber Monday is November 30. If your winery is still finalizing its holiday offers, you have time. But with a few weeks left, I would focus on getting a handful of things right.
What do you want customers to buy? Who has a reason to buy it? And what would make that purchase easier?
A strong winery Black Friday and Cyber Monday campaign brings together thoughtful wine bundles, relevant customer segments, shipping offers you can afford, and a website that makes buying easy. The discount is one part of that.
Decide what each holiday offer should accomplish
Before choosing a percentage, decide what you want the promotion to do. Are you trying to move a typical three-bottle purchase to six? Bring back customers who have not ordered since spring? Sell a limited library selection? Help someone finish their client gifting?
Those are different goals. They need different offers.
In my earlier article, Black Friday for wineries: Bundle before you discount, I covered building bundles around the purchase someone needs to make.

The bottle count follows the occasion. A collector set may need two wines. A holiday gathering may call for a case.
Pairing a slower-moving wine with a bestseller can make sense, but the wines still need a reason to belong together. A holiday bundle should feel like a thoughtful selection, not inventory you needed to move.
Build the audience alongside the offer
A club member who received a shipment last week, a visitor who purchased three times this year, and someone who buys one gift every December should not automatically receive the same message.
Corksy’s new AI-powered Segment Builder lets you describe the customers you want to reach in plain English, review the filters Corksy creates, and adjust them before saving. You can also build an audience directly from the filter library.
The builder uses purchase and membership history across POS, online, club, and admin orders. That matters when a customer buys regularly in your tasting room but rarely shops online.

Save a dynamic segment when you want the audience to stay current as customers meet or leave your criteria. Use a one-time segment when you need a fixed list for a particular campaign.
Look at last year’s holiday buyers, too. If you track gift purchases through tags or order details, use that history. A December purchase alone does not tell you someone was buying a gift.
Before sending, check consent and suppression settings in your email platform. Review overlapping audiences and recent purchases so customers do not receive every version—or another reminder for something they already bought.
Protect wine club value before opening the sale
Your members are likely to see the public promotion. Before it goes live, make sure they still have a reason to feel good about belonging.

New members may need an explanation of how to use their benefits. Longtime members may simply need their early-access link and the date the public sale begins.
Give your tasting room and customer service teams the same information. They should be able to explain the offer without working through the rules while a customer waits.
Calculate shipping and discounts together
Free shipping has a cost. So does the gift box, the added accessory, and the extra packing time.
Run the full order calculation before approving the offer.

For example, a $240 order with a 15% discount produces $204 in revenue. If the winery also pays $30 in shipping, $174 remains before wine, packaging, fulfillment, and payment costs.
Set thresholds around the purchase you want to encourage and the costs you can support. If most customers already purchase six bottles, a six-bottle shipping threshold may subsidize their usual order without encouraging a larger purchase.
When setting up your promotion in Corksy, confirm the eligible products, minimum purchase, dates, exclusions, and shipping terms. Then test the offer as a customer.
Make the terms visible before checkout. Nobody should have to build a cart to find out whether the offer applies.
Make the gift easy to understand on a phone
A holiday gift buyer may love your winery but have no idea which bottles their boss, neighbor, or in-laws would choose.
Answer the practical questions first. Then provide the wine details for shoppers who want them.

Use a dedicated holiday page organized around recipients and occasions. Someone who clicks an email about a gift set should arrive at that set.

Example holiday gift-guide layout for a winery storefront.
The images need to match what arrives. Show all the bottles, use the correct vintage and format, and make included packaging visible. If a serving towel is a styling prop, do not leave shoppers guessing whether they get one.
Before launch, complete purchases while logged in as a member, logged out, and on mobile. Check pricing, codes, inventory, gift messages, shipping, pickup, and confirmation emails.
If the email promises a benefit, make sure the customer sees it applied correctly before payment.
Keep the weekend offer consistent and vary the message
A small team does not need four separate promotions to cover four days. Choose a core offer, then give each email a purpose.

Show collectors the library selection and previous gift buyers the packaged gift set. The promotion can stay consistent while the featured products and message change.
Be precise about deadlines. The end of a Cyber Monday promotion and the last date to order for holiday delivery are different things. Publish delivery guidance based on your fulfillment schedule and current carrier information.
Put the next three weeks to work

The work that tends to get squeezed is the work between creating the offer and fulfilling it: testing links, checking member pricing, ordering packing materials, and making sure the team knows what customers were promised.
Give that work a place on the calendar.

After the weekend, look beyond total sales. Did customers buy more bottles per order? Did the shipping offer leave enough margin? Did customers who had gone quiet come back?
Track new customers separately, then watch whether they order again. That will tell you more about what to repeat next year than revenue alone.
Build your holiday audiences in Corksy
A customer may buy in your tasting room, receive club shipments, and order gifts online. Your holiday planning should account for that full relationship.
Corksy brings ecommerce, POS, wine club, and customer history together. The new Segment Builder helps you put that history to work before the first holiday email goes out.


