Why Executive Retreats Are Moving Beyond the Usual Big Cities

Executive retreats, board meetings, leadership summits — these VIP-level programs may have different aims, but they all share a common challenge: impress participants who have seen it all. They’ve already been spending a significant portion of their professional time on the road. Past Skift research has shown that nearly half of business travelers took at least six professional trips in the past year. That figure is likely to increase among executives with bigger travel demands.

All those extra nights in cities around the world create bigger pressure for meeting planners to find the right host destination. They’re increasingly expanding their consideration sets beyond the typical first-tier hubs to tap into one-of-a-kind culture in surprising cities like Louisville. When they do, they’re finding that it’s easier to deliver the special touches these programs require. 

“For VIP audiences, personalization matters,” Jason Sojka, vice president, convention development, Louisville Tourism, said. “In Louisville, it’s easier to secure meaningful access — private museum tours, behind-the-scenes experiences at Churchill Downs, custom distillery programming — without the scale challenges you encounter in larger markets. We deliver sophistication without complication.”

Why Leadership Gatherings Need More Than a Luxury Setting

Participants at board meetings and executive summits will expect four- and five-star accommodations, but that’s merely the baseline. These programs need to help propel the business to greater heights. To create the real kind of value that these programs seek to deliver, meeting planners must be able to introduce participants to local innovators and business leaders who can help unlock new ways of thinking. 

“We focus on connecting the event into our ecosystem,” Zack Davis, vice president, destination services, Louisville Tourism, said. "It's not just about providing services—it's about helping tap into what makes Louisville unique. Local partners bring knowledge, culture, and resourcefulness from working and living in our community.”

It’s a two-way street, too. In addition to what those local partners bring to the meeting, forward-thinking planners are focused on what the meeting can do for those local partners. 

“We measure impact across the full ecosystem, looking at how our meeting shows up in the community through economic contribution, support of local businesses, environmental responsibility, and opportunities to give back,” said Lori Granich, senior director of lifelong learning and meeting operations, Academy of Nutrition and Dietetics and a member of Louisville Tourism’s Client Advisory Council. “That holistic view ensures our events don’t just take from a destination, but actively contribute to it in meaningful, measurable ways.”

How Louisville Elevates Small-Group Programs

Sojka said that Louisville has seen an uptick in interest among planners for board meetings recently. Part of the surge is due to a mix of iconic infrastructure, including The Brown Hotel, a 294-room historic property where the city’s most famous sandwich was born, as well as new boutique concepts such as the 168-room Hotel Bourré Bonne, a Hilton property. 

However, what really sets Louisville apart is a collection of off-site venues brimming with the city’s energy.

Learn how Louisville can reshape your next program with a new report.

Using Entrepreneurial Storytelling to Spark Bigger Thinking

Before he was Muhammad Ali, he was Cassius Clay, and before he was anybody, he trained at Headline Boxing Gym. Now, the former gym is the site of Stitch, an intimate speakeasy owned and operated by beloved Louisville leather goods maker, Clayton & Crume. The space is located above the flagship store, offering a tucked-away environment where attendees can pair a bourbon tasting with lessons about the company’s growth from a college dorm room to being featured in Men’s Journal, Forbes, and Good Morning America.

And for planners who want to mix stories of business innovation with authentic Kentucky cooking, the 2,400-square-foot event space at Bourbon Barrel Foods offers culinary courses that celebrate Louisville’s palette. Led by founder Matt Jamie – the first person outside of Japan to micro-brew soy sauces – the courses offer participants a look at surprising flavor pairings. It’s a lesson that applies to every business leader: Sometimes, the most unexpected combinations deliver the most rewarding results.

Leveraging Interactive Experiences to Bring Bourbon to Life

It’s easy to plan a bourbon tasting anywhere. In Louisville, however, groups don’t simply “taste” bourbon. They shake hands with the distiller who made it, learn the story behind it, and leave with a one-of-a-kind bottle for their bars. At Big Bat Bourbon, located next to The Louisville Slugger Museum & Factory, attendees can choose from six wood-finished recipes, blend their own custom bottle,  and take it home as a one-of-a-kind souvenir.

Encouraging Strategic Focus With the Right Retreat Environment

When Bob Moore, executive director of the American College of Osteopathic Family Physicians (ACOFP), came to Louisville, his group took the 20-minute journey from the bustling downtown to the tranquility of Hermitage Farm, a 700-acre thoroughbred estate in horse country. “There were so many opportunities to connect over derby horses, bourbon, and dinner,” Moore, who will host the 2027 edition of the ACOFP Annual Convention & Scientific Seminar in Louisville, said. “Learning about the farm’s connection to the Kentucky Derby and then enjoying an excellent farm-to-table dinner really made us appreciate the local culture.”

For planners with groups who crave a deeper ability to focus, the property’s five-bedroom Main House is available for full buy-outs.

A City That Wants to Show You Around

As Louisville continues to evolve, the local community of travel and event professionals is committed to showing off those venues and telling the story of how the city has transformed into a premier meetings destination. Anna-Marie Frazier, founder of Destination Louisville and long-time Louisvillian, has enjoyed a front-row seat to the city’s changes.

“I’ve seen it grow and mature as a destination,” Frazier said. “We have the cost benefits that come from being a freight hub and the innovative approaches that come from the university and our robust small business community. Louisville innovators are constantly putting us on the map.”

Sojka, who relocated to Louisville after several years in Dallas, believes that kind of excitement is one of the key factors that differentiate bringing a group to Louisville. 

“People are passionate about this city and genuinely want to share their favorite restaurants, bourbon spots, neighborhoods, and traditions,” Sojka said. “You’re not walking into a polished but impersonal environment. You’re engaging with people who care deeply about where they live and what they represent.”

Ready to learn more about how those people, traditions, and neighborhoods deliver a different kind of meeting? Download a new report created in partnership between Skift Studio and Louisville Tourism. And if you're looking for a customized proposal for your next executive program, head to https://www.gotolouisville.com/meeting-planners/.

This content was created collaboratively by Louisville Tourism and Skift Studio.