How to Sell High-End Travel Packages: Expert Tips from Jim Kennedy

Most travel advisors in Canada earn about $50,000–$60,000 per year, but wouldn’t it be great to hit $100,000+? The bad news is, most advisors never get there. The good news? It’s possible—and realistic.

The secret is shifting from selling discounted, mass-market travel to offering high-end luxury travel packages with higher margins. Ironically, although luxury travel is more profitable, many advisors still struggle to sell it.

To dig into how to succeed in this space, we spoke with Jim Kennedy, a travel concierge with over 40 years of experience selling luxury packages. Jim has seen it all—and today, he’s sharing exactly what works when it comes to closing those high-ticket sales.

1. Help Clients Understand That Luxury Isn’t Always More Expensive

A lot of clients assume luxury means "out of budget"—but that’s not necessarily true.

“People say they don’t want to go on a luxury cruise because it’s too expensive. But when you add up all the extras on a mainstream cruise—gratuities, drinks, specialty dining, excursions—you’re being nickeled and dimed,” says Jim.

He uses side-by-side comparisons of lines like Royal Caribbean or Princess vs. Oceania or Azamara, showing that the cost difference is often minor, especially when everything is included in the luxury experience.

2. Sell the Memory, Not Just the Trip

“You’re not just selling a cruise. You’re selling a memory,” Jim says.

He reminds clients that travel is about creating moments they’ll remember for a lifetime—especially when everything is seamless and special. A butler, a suite upgrade, a surprise dinner—these become part of the story. The cost fades. The memories stay.

3. Educate Your Clients

Jim invests in education—both for clients and newer advisors. He recently launched a seminar series called “Cruising 101” to walk clients through cruise options, benefits, and best practices.

“When I get back from holidays, I do live seminars using a PowerPoint presentation that explains what cruising is all about. I also use the TravelAndCards tool to help educate my clients about travel insurance and ensure they understand their coverage options. Education builds trust and helps clients feel confident choosing premium options.”

4. Build Trust by Showing Up—In Person

“Internet ads don’t build trust. Networking does.”

Jim urges advisors to attend local business events, network with entrepreneurs, and get out into the community. That face-to-face connection is what earns trust—and trust is what leads to high-value sales.

“Yes, it takes time—coffee meetings, driving across town—but the return is worth it. People remember who helped them, and they come back to you.”

5. Add a Personal Touch to Keep Clients Coming Back

Jim’s client care doesn’t stop after the trip ends.

“When my clients return, they get a ‘Welcome Home’ card in the mail. It says, ‘Hope you had a great trip—don’t forget to plan the next one!’”

He also uses tech tools to track passport expiry dates, birthdays, and anniversaries, helping clients avoid costly mistakes and showing that he’s looking out for them.

“I had a client whose child’s passport had expired—she didn’t know. That trip would’ve cost them $3,200 if they’d gone ahead without realizing. I caught it because I track these things.”

6. Be Professional—Even With the Boring Stuff

Jim is meticulous about how he handles sensitive information.

“I collect credit card details using a secure authorization form, and I tell clients that once the cruise is over, I shred it. I don’t keep anything on file. It builds trust—and shows I take their security seriously.”

It’s the little details like this that make a luxury experience feel truly professional.

7. Plan Ahead—and Show Clients Why It Pays Off

Luxury travel clients don’t just book last-minute getaways—they plan years in advance.

“I send out flyers for trips in 2026 and 2027. A small, refundable deposit locks in the price—and I monitor fares every week to see if I can rebook them at a lower rate.”

Jim recalls helping a couple save $1,700 on a round-the-world Princess cruise simply by watching the fare changes. That kind of ongoing attention makes him more than an agent—it makes him a trusted travel broker.

About Jim Kennedy

Jim Kennedy is an independent travel advisor with over four decades of experience across the airline, hotel, government, and cruise sectors. Known for his dedicated, concierge-level advisor and sharp industry knowledge, Jim helps clients travel by Air, Land, and Sea—with value, clarity, and comfort every step of the way.