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5 Ways Your Winery Can Strengthen Customer Connections (and Sales) This Holiday Season
10/27/2025
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For wineries, the holidays are more than a busy season. They are an opportunity to connect with customers who are searching for gifts, planning gatherings, and looking for memorable experiences to share.

The challenge is that many of these interactions now happen online. Instead of asking your tasting room team for pairing advice, guests are browsing your website on their phones, hoping to find the perfect bottle for someone special.

That is where smart DTC strategies come in. Imagine a customer scrolling alone on their phone, overwhelmed by options without a guiding hand. The wineries that stand out this time of year are not simply selling more, they are using digital hospitality to transform that solitary search into a guided discovery, creating the same warmth and confidence customers feel in person.

Here is how you can do the same this season.

1. Turn Browsers into Buyers with Real-Time Webchat

Over the shoulder view of a team member assisting a shopper via website chat, natural light office scene
Bring your tasting room hospitality online with real time guidance.

Think about how your tasting room team uses warmth and expertise to help guests find the right wine. With webchat, you can bring that same experience to your website.

By adding RedChirp to your site, your staff can help online visitors choose the right gift or answer questions before they click away. Encourage your team to guide shoppers with questions like:

  • Who are you shopping for
  • What is your price range
  • Do they prefer red, white, or sparkling
  • What kind of food do they usually enjoy

These simple questions create the same one on one interaction customers enjoy in person. If someone mentions seafood, you might suggest your crisp Sauvignon Blanc. If they talk about pasta, you could recommend your Sangiovese.

If your winery uses vinSUITE eCommerce, RedChirp integrates directly so conversations can be saved to customer profiles for follow up and personalized offers.

2. Reconnect with the Customers Who Already Love You

Your best prospects this season are the customers who already know you. The ones who ordered last November or gifted your wines last December are already in a buying mindset, and you have the data to reach them.

Using ListBuilder in vinSUITE marketing, you can filter past buyers by SKU and date range to identify high intent audiences. For example, filter customers who purchased Cabernet Sauvignon last holiday season and send targeted emails featuring this year’s vintage.

Follow up with messaging that recalls their last purchase, offers a timely incentive, or invites them to a pickup or virtual tasting. Targeted outreach feels personal, not pushy, and makes it easy for customers to say yes again this year.

3. Help Shoppers Give the Perfect Gift

Elegant wine gift set with subtle seasonal packaging on a clean tabletop
Make gifting easy across your website and tasting room.

Holiday buyers rarely need convincing to give wine, they need help choosing how to give it. Make it simple and visible across all your channels.

  • Gift cards, Valutec integrates with vinSUITE so customers can purchase digital or physical cards through your online store
  • Club gifting, share your Give the Gift of Club webinar to show how easy it is to gift a membership
  • Kits, refresh existing bundles with seasonal packaging or naming, see the kit setup guide to keep operations clean

The goal is not to launch new products, it is to remind customers that giving wine is easy, personal, and enjoyable, and that your winery makes it even easier.

4. Capture Holiday Visitors While Excitement Is High

Guest signing up for a wine club on a tablet at the tasting bar
Make joining simple in the moment, and offer a way to join later.

The holidays bring a steady stream of new guests into your tasting room. Each visit is a chance to turn a first time taster into a long term club member.

Set up a tablet in Kiosk Mode for quick, paperless signups. The form automatically refreshes after each new member, which keeps the process fast for guests and staff. For visitors who want to think about it later, place QR codes on menus or near checkout that link directly to your online signup form.

You can find more tips in vinSUITE club management.

5. Keep Every Channel in Sync

Promotions, discounts, and shipping offers are key parts of any holiday plan, but when they are not coordinated, they can lead to confusion. A ten percent discount promised on a product page but missing at checkout can damage trust.

Review vinSUITE ‘Tis the Season for Promos to see how scheduled promotions align POS and eCommerce. For in room specials, share the Tablet POS discount overview with your team.

Before the season peaks, run this quick checklist:

  1. Verify promotional codes and expiration dates
  2. Test promotions on every platform before they go live
  3. Brief staff on current offers so they can answer questions
  4. Monitor active promotions and address inconsistencies quickly
  5. Have a plan to resolve customer issues promptly

Connection Builds Conversion

The holidays have always been about connection, with family, with friends, and with your customers. The wineries that succeed this time of year are the ones that extend that connection across every channel.

From a quick conversation on your website to a personalized follow up email, every interaction builds trust and loyalty. With the right tools and a customer first mindset, your winery can deliver the same warmth online that it does in person, and turn that hospitality into measurable growth.

 
Post By:   vinSUITE
 
 
 
 
 
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