We’ve put together five simple strategies to help your staff boost sales and enhance the guest experience—without ever feeling pushy.
Upselling in the tasting room can feel like a delicate dance. Done right, it enhances the guest experience, boosts sales, and builds loyalty. Done wrong, it can come across as pushy and diminish the magic of the visit. The key is training your team to upsell in a way that feels natural, authentic, and customer-focused.
Here are five practical ways to get your team comfortable and confident with upselling—without ever sounding like a salesperson.
Guests visit your winery because they want to learn, taste, and explore. Encourage your team to frame recommendations as insights rather than pitches. For example, instead of “Would you like to buy a bottle?” try “This wine comes from our oldest vines, and many guests love to take a bottle home so they can revisit the story later.” Education builds value, and value naturally drives purchases.
Stories create emotional connections that guests remember long after the tasting ends. Train your staff to share the history of the vineyard, the challenges of a vintage, or a fun anecdote about the winemaker. A story about how a wine pairs beautifully with Thanksgiving dinner is much more compelling than simply naming a price.
The words your team uses make a huge difference. Instead of yes-or-no questions that invite rejection, suggest options:
Wine clubs are the lifeblood of most tasting rooms, but pushing a membership too hard can turn people off. Instead, have your staff weave the benefits naturally into conversation. For example: “This wine is available today in the tasting room, but members enjoy guaranteed allocations every year.” By positioning the club as an insider’s opportunity rather than a sales tactic, guests see joining as a privilege.
Even the best training falls flat without reinforcement. Recognize and celebrate when your staff nails an upsell in a natural, guest-focused way. Share success stories at team meetings, provide ongoing coaching, and offer small incentives for upselling done right. This creates a culture where upselling feels like enhancing hospitality—not pushing product.
Upselling doesn’t have to feel awkward. With the right training, your team can present it as an extension of great hospitality—helping guests discover wines, experiences, and memberships they’ll genuinely enjoy. The result? Guests leave with fond memories, a little extra wine in their hands, and a deeper connection to your brand.
