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Why ‘Upselling’ Isn’t a Dirty Word in Travel (and How to Do It Right)

by Sarah Milner  June 29, 2026
A travel agent handing a woman her passport after booking her travel for her

Photo: Shutterstock.com

In an industry built on personal relationships, “upselling” can be a challenge for travel advisors. The term itself often has a negative connotation due to the implication of pressuring consumers to spend more for the sake of increasing sales. Yet, not upselling your clients can create problems too. Not only does it risk leaving money on the table, but clients may miss out on experiences, conveniences, or added peace of mind that would improve their vacation experience.

Gillian Fripp, an experienced travel advisor from Ontario, Canada, led a breakout session on the subject of upselling at the most recent Travel Market Place Toronto. Titled “And Do You Want Fries With That? Rethinking the Art of Upselling,” the 45-minute workshop dove into best practices for maximizing sales while giving clients the best service possible.

“Upselling isn’t just about selling more… It’s really about improving the experience for your clients,” said Fripp.

Sell the Experience, Not the Product

Fripp led an interactive workshop at TMP Toronto, inviting participation from the travel advisors in attendance. Her core message: “upselling” doesn’t have to be a dirty word. She suggested reframing the concept, both in how one approaches upselling as an advisor, and how one frames the additional-charge options to clients.

“It’s not about selling the product. It’s about selling the benefit,” Fripp said. “You’re selling happiness, you’re selling memories, you’re selling experiences.”

Fripp used an Alaska cruise as an example, suggesting advisors help clients visualize the experience rather than just as what stateroom category they prefer. Instead of “do you want a balcony cabin?” she recommended saying something like, “imagine sitting on your balcony in Alaska with a cup of coffee while the glaciers drift by” — focusing on what it would be like to have a balcony, and setting the bar from there.

Utimately, upselling works best when advisors focus on the emotional element rather than getting bogged down in dollar amounts, warning that if you find yourself stuck on comparing options based on price alone, you’ve already “lost the point” that you’re selling them the experience.

Comfort, Convenience, & Confidence

TMP Toronto 2026 breakout session Upselling Gillian Fripp
Gillian Fripp led a breakout session on the art of upselling. Photo: Sarah Milner

Fripp said that selling the experience effectively comes down to three main priorities for clients: comfort, convenience, and confidence.

Comfort is pretty obvious: it’s what a client needs in order to both physically and emotionally enjoy their travel experience. What’s important to remember is that comfort can mean different things to different people. While one client may want a large suite, for another, comfort could be separate beds.

“It’s not necessarily finding the best upsell, it’s finding the right upsell,” Fripp said. “You really have to think about your client and their needs and not about yours.”

Convenience, meanwhile, covers upsells that make traveling more seamless — whether that’s a pre-arranged airport transfer or a hotel located very close to a cruise terminal. Fripp encouraged the advisors in attendance to think beyond the most common pain points in travel: not just airport transfers and pre-cruise hotels, but also things like airport lounge access or private sightseeing tours post-cruise.

“People spend money to either make their vacation feel a little bit longer, or to save the hassle,” Fripp said.

Finally, confidence comes down to taking care of traveler anxieties before and during their trip. A great example of this is travel insurance, which gives travelers the confidence to book since they know they’ll be covered if they have to cancel their trip or if there’s an emergency during travel.

“The number one upsell really is a no-brainer. It shouldn’t even be considered an upsell,” Fripp said of travel insurance. “You’re selling confidence, you’re selling the peace of mind.”

Some upsells function across categories. A pre-cruise hotel, for example, is not only added convenience but also added confidence since it gives travelers that peace of mind that they won’t miss their sailing due to flight delays. Advisors can cater the suggestions to each client’s priorities, needs, and wants; the important thing is to ask those qualifying questions like “what are you celebrating” and “is this a once-in-a-lifetime trip?”

Fripp ended with the ultimate upsell: group travel. She recommended advisors ask “who are you traveling with” or “who else would like to come” during the booking process, arguing that can lead to significantly more bookings. Just because a client hasn’t thought about who else might like to experience the trip doesn’t mean there aren’t people in their life who would. That single question, she said, can turn one booking into several with relatively little additional work.

“Good upselling isn’t about convincing someone to buy something they don’t want,” explained Fripp. “It’s about helping them discover something they may not have considered.”

  
  
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