Uncork More Profit: 5 Upsell Secrets for Your Winery’s Holiday Events

The holiday season is your winery’s biggest opportunity to create lasting memories and loyal customers. Twinkling lights and festive music create the perfect backdrop, but a truly successful season goes beyond ticket sales and booked private events. How do you turn a one-time visitor into a lifelong fan and maximize your revenue without being pushy?

The secret lies in strategic upselling that enhances, rather than interrupts, the guest experience. This guide will show you how to thoughtfully integrate premium offerings that will delight your guests and significantly boost your holiday profits.

1. Don’t Just Pour, Dazzle: Curate Premium Tasting Flights

While your standard tasting menu is always a hit, the holidays are the perfect time to introduce something truly special that commands a premium price.

• Reserve & Library Wine Flights: Offer a curated selection of older vintages or limited-release wines that aren’t typically available for tasting. Position these as an exclusive opportunity for true connoisseurs to taste the history of your vineyard.
• Vertical Tastings: Showcase the evolution of a single varietal over several years. This offers an educational and unique experience that showcases your winemaking expertise and will be deeply appreciated by wine enthusiasts.
• Food & Wine Pairing Flights: Partner with a local cheesemonger, chocolatier, or gourmet food producer to create flights that perfectly complement your wines. Think sparkling wine with artisanal truffles or a rich Cabernet with aged cheddar.

Revenue Booster: Ensure your event staff is well-trained and versed in the stories behind these premium wines. Storytelling sells. Guests are far more likely to upgrade when they understand the unique value and history of what’s in their glass.

2. Think Inside the Box: Create Irresistible Gift Baskets

Gift baskets are a holiday staple, and your winery is perfectly positioned to create memorable ones that sell out quickly. Think beyond just a bottle.

• Curated Wine & Swag Baskets: Pair a popular bottle with high-quality branded merchandise, such as elegant wine glasses, aerators, or a cozy, winery-branded throw blanket.
• Gourmet Foodie Baskets: Pair your wines with local delicacies. Highlight regional producers, such as local creameries, bakeries, and olive farms, to add a touch of local charm and community support.
• “Experience” Baskets: Go beyond physical products. Include a gift certificate for a future wine tasting, a private vineyard tour, or even a winemaking workshop.
• Themed Baskets: Create concepts like a “Cozy Winter Night” basket featuring a red blend, a scented candle, and local chocolates, or a “New Year’s Celebration” basket with sparkling wine and gourmet snacks.
• Interactive “Build-Your-Own-Basket” Station: Create a fun, engaging station with various wines, foods, and merchandise where guests can create a personalized gift at their own price point.

Merchandising Tip: Display beautifully assembled sample baskets in prominent locations. Clear pricing and simple ordering forms (or QR codes) are key to making the purchase decision effortless.

3. From Guest to Family: Convert Visitors into Club Members

Holiday events are prime opportunities to convert enthusiastic guests into loyal wine club members.

• Exclusive Holiday Enrollment Offers: Sweeten the deal for guests who sign up during your event. This could be a discount on their first shipment, a complimentary bottle of reserve wine, or exclusive access to a members-only event in the new year.
• “Member for a Day” Experience: For a small upcharge on their event ticket, allow guests to receive the wine club discount on all purchases made that day. This is a powerful, tangible preview of the benefits.
• VIP Tasting Area: Set up a dedicated, slightly more private tasting area for wine club members and potential new sign-ups. Offer them a taste of a special wine not available to the general crowd. This creates an air of exclusivity and desire.

4. Beyond the Bottle: Offer Merchandise They’ll Love

Don’t underestimate the appeal of quality merchandise that extends your brand beyond the wine itself.

• High-Quality Apparel: Branded t-shirts, hats, and hoodies can be excellent sellers, especially if they’re stylish, comfortable, and made from premium materials.
• Home Goods: Consider items like wine-themed coasters, tea towels, custom charcuterie boards emblazoned with your logo, or even scented candles with notes inspired by your wines (e.g., “Cabernet & Oak”).
• Bundles and Promotions: Encourage multiple purchases by bundling items. For example, “Buy a hoodie and get 15% off a bottle of your choice” or “Purchase any two glasses and receive a free branded wine stopper.”
  

5. The Secret Ingredient: Train Your Team for the ‘Soft Sell’

Your best offerings will fall flat if your team isn’t trained to present them correctly. The goal is to make every upsell feel like a helpful, insider suggestion.

• Focus on Storytelling: Train staff to tell the story behind the library wine, the local cheesemonger, or the artist who designed the coasters. Passion is contagious.
• Teach Them to Read Cues: A couple on a romantic date might be interested in a “New Year’s Celebration” basket, while a group of aficionados would be the perfect audience for the vertical tasting.
• Practice the Approach: Role-play scenarios to master the “soft sell.” Instead of “Do you want to join the wine club?”, try: “Since you enjoyed the Cabernet Franc so much, I wanted to let you know it’s one of the exclusive bottles in our upcoming club shipment. Members get first access.”

Key Points on What to Avoid

• The Hard Sell: Upselling should never feel transactional. It’s about enhancing the guest’s good time, not just padding the bill.
• Choice Paralysis: Offering too many options can overwhelm guests, leading to indecision. Keep your premium offerings clear, curated, and concise.
• Checkout Friction: A long line to pay for an extra bottle or gift basket can ruin the festive mood. Ensure your staffing and payment systems are efficient.

Your Most Organized and Profitable Season Yet—Powered by Tripleseat

By shifting your focus from simple sales to creating enhanced experiences, these upsell opportunities become a natural part of the holiday magic at your winery. They allow you to share more of your story, deepen guest loyalty, and finish the year on a high financial note.

As you plan these special offerings, managing the details for holiday parties and private gatherings becomes crucial. Tripleseat is the event management platform designed to help wineries like yours streamline the booking process and maximize revenue.

Tripleseat is designed to help wineries master the busy season by:

• Capturing Every Lead: Never miss a lucrative holiday party inquiry again. Our platform centralizes all leads from your website, social media, and phone calls into a single, organized dashboard, enabling quick and professional follow-up.
• Booking Faster: Respond to interested guests in minutes, not days. Create and send stunning, detailed proposals and contracts with just a few clicks, securing deposits and signatures electronically before the competition can.
• Keeping Your Team in Sync: From the tasting room to the kitchen, ensure everyone is on the same page. Tripleseat’s detailed Banquet Event Orders (BEOs) and shared calendars mean your team knows exactly what to prepare and when, ensuring every upsell—from a premium flight to custom gift baskets—is executed perfectly.
• Tracking Your Success: Instantly see your holiday sales, track your most profitable events, and create detailed reports. This data is invaluable for seeing your ROI and planning for an even more successful season next year.

Ready to make this your most organized and profitable holiday season yet? Schedule a demo to see how Tripleseat can help.