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Entrepreneur Travelers Embrace Flexibility but Also Face Unique Challenges

by Holly Riddle

Jan 13, 2026

Lisbon is a popular destination for business travelers © Aleksei Todosko | Dreamstime.com

January 2026

Business travel is business travel … right? Well, not if you’re an entrepreneur. Traditional business travelers are beholden to corporate travel policies, forced to book via a dedicated platform or with certain brands, and restricted by their employers’ duty of care. When it comes to entrepreneur travel, however, anything and everything is an option — and travel brands, from airlines to hotels and beyond are taking notice and adjusting their offerings accordingly.

“Entrepreneurs can personalize everything about a trip. We have more freedom to set our schedule. Traditional corporate travel is tight with company policing and [a] schedule and budget. [Entrepreneurs] can choose destinations based on opportunity. We can be more fluid in our schedules to blend purposes on a given trip,” said Valerie Bihet, CEO, VIBE Agency, a corporate event planning and production company.

With so much freedom at their disposal, entrepreneurs are taking typical business travel trends and making them all their own. Take, for example, bleisure travel, which has trended for years but has evolved according to the ever-changing travel landscape. The COVID-19 pandemic, a move toward more remote work and similar trends have all affected bleisure travel to a degree. And even though it’s made headlines for a while, you’ll still see numerouscorporate think pieces published on a regular basis, mulling over employees’ bleisure travel habits and whether or not this type of travel is just a trend or here to stay, and whether it’s a pro or con for employees.

© Martinmark | Dreamstime.com

However, when you move beyond the corporate world and look at the travel habits of the self-employed, combining leisure and business travel is just an extension of the work-life blend-rather- than-balance many already adopt.

“Entrepreneurs are increasingly merging business with lifestyle. They travel more freely, often combining work with personal exploration, wellness and family time,” said Jason Stevens, CEO, Wayfairer Travel. “We see them choosing multistop itineraries that balance productivity with inspiration — for instance, working remotely from an eco-villa in Bali, then spending a few days diving off Komodo National Park or skiing in Japan. Their itineraries are designed to be immersive and efficient rather than purely transactional.”

Wayfairer Travel is a luxury travel company offering expert-designed itineraries. It boasts a client base of predominantly high-net-worth individuals, many of whom are business owners and entrepreneurs, including Fortune 500 CEOs, chairmen and founders of startups or recently acquired companies. These types of clients amplify the bleisure trend beyond what most corporate travelers can manage.

“[Entrepreneur travelers are] not just following the bleisure trend — they’re defining it,” commented Christal Bemont, CEO, travel management company Direct Travel. “For entrepreneurs, the line between work and personal time is inherently fluid. They’ll add days to recharge, move locations to stay inspired or bring family along when it aligns. This isn’t about escape; it’s about designing travel that supports their well-being, creativity and the longevity of their work.”

This enhanced blend of business and leisure can also be seen in the destinations to which entrepreneur travelers are most likely to flock. Bemont sees entrepreneur travelers gravitating toward destinations such as Dubai, Austin, Miami, Barcelona, Lisbon and Singapore, where business and lifestyle intersect seamlessly. Mitch Rodriguez, co-founder and CEO, Brickell Travel, a business travel agency owned by Talma Travel Solutions, likewise mentioned Austin, Singapore, Dubai and Lisbon as popular among entrepreneur travelers, alongside London, Berlin and Tel Aviv.

© Martinmark | Dreamstime.com

Bleisure isn’t the only travel trend attracting entrepreneurs, though. Increasingly, women engage in solo travel, a fact that continues to make headlines — and women entrepreneurs are a big part of this growth.

It’s something Doni Belau, founder, women-only travel company Girls’ Guide to the World, has witnessed firsthand. “In our business, we have quite a few entrepreneurs who travel with us. They may be doctors, lawyers, CPAs, financial advisors, business owners and the like. I would guess they represent about 25– 30 percent of the female travelers we work with. …What we observe is that the number of female entrepreneurs who travel solo continues to accelerate year over year,” Belau said. “This percentage will only continue to increase.”

She added, “Female entrepreneurs are now prioritizing their time off because most of them are working longer hours than ever before, and they’ve read the studies showing that taking at least two vacations a year and unplugging from work helps relieve stress, lets you live longer and makes you more productive back at the office.”

The slow travel trend has also caught entrepreneur travelers’ attention, Rodriguez mentioned, with longer stays in destinations that allow them to truly tap into the local community. Belau likewise said she personally, as an entrepreneur traveler, makes it a priority to take more time in a destination.

“Along with my husband, as he works with me, we can rent a place in Timbuktu for a month and really get to know the place, feeling like locals after a few weeks,” she said.

So, how are brands breaking from the mold and adjusting to serve these travelers in particular? Airlines, for one, are becoming more flexible in their booking options. Then, hotels are adapting by rethinking their business travel amenities. Rather than just offering large conference and meeting spaces, they might provide workspaces geared toward only one or two people. They might also provide better-outfitted in-room workspaces. Lifestyle hotel brands are blending leisure experiences with these amenities.

New hotel brands — including Hilton’s LivSmart Studios and Marriott’s StudioRes — are arising that specifically cater to those business travelers booking longer stays.

Still, some brands could stand to further refine their offerings to meet entrepreneurs’ needs. As Mario Del Duca, managing director, luxury travel agency NUBA, noted, “Many travel providers remain structured around corporate efficiency, not entrepreneurial fluidity.”

Additionally, while entrepreneur business travel, with all its freedom, can seem like all pros and no cons, this specific cohort of travelers face their own challenges.

Mel Suntal, founder and CEO, Axonall, an intelligent luxury travel platform, explained, “ … Entrepreneur travelers [are] managing everything themselves. They have limited resources. There’s no large corporate structure or support departments behind them. So they’re the ones booking flights [and] hotels and handling last-minute changes. When delays or cancellations happen, there’s no 24/7 support line to call, which can easily throw off their entire schedule.

“We also see burnout creeping in. Many of them fly solo and try to make every minute count. In theory, that sounds productive, but it often ends in exhaustion. These guests mostly fund their own travel, so they have to find a balance between comfort, cost and the return.”

As Bihet likewise said, entrepreneurs are also thinking about business back home when traveling. They can’t quite be as single- minded as perhaps a traditional business traveler can be, completely focused on the trip at hand.

However, if entrepreneurs can strike the right balance, they’ll be well-rewarded. Besides, Belau pointed out, traveling as an entrepreneur and leaving your business baby behind is a bit of a litmus test. If your company can stand on its own while you’re away, it’s a sign you have something good on your hands.

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