How Company Retreats Are Changing Business Travel

Business travel used to mean sending employees from their home office to somewhere else — to meet with clients or coworkers at other offices. But for many remote-first companies, it now means the opposite: Bringing employees together from their far-flung homes to work and meet in person.

These so-called “off-sites” — a holdover term from when these companies had actual sites — have the potential to change the face of business travel.

While consumer travel has roared back in 2022, business travel has been slower to rebound. Company off-sites could make up a larger share of that budget than in years past.

Doist, a software company with employees distributed around the globe, wanted something different for its companywide retreat in July.

“We rented a small village in the Austrian Alps,” says Chase Warrington, head of remote at Doist. “We did a lederhosen party and went to traditional lodges for dinners.”

Warrington says the purpose of these off-site gatherings differs markedly from the goals of traditional business travel. Rather than hunkering in meetings to get work done, these retreats aim for connection and fun. That means throwing out the traditional business travel playbook.

» Learn more: Your guide to business travel insurance

Business or pleasure ... or something else?

Rather than replacing traditional business travel, the off-site retreat is seen by many as an emerging trend of its own.

“There will still be business travel, it will just look different,” says Bruno Muchada, head of expansion for property partners at Surf Office, a company retreat management company. “You’re traveling to see your company as much as you are going to see clients.”

And as the line between business and pleasure blurs into so-called “bleisure” travel, off-site organizers are recognizing the relative unimportance of traditional meetings and schedules. In this upside-down scenario, employees are now working at home and playing with their co-workers at the “office,” instead of vice versa.

“I have this theory on the division of the structure of the day,” says Warrington, who also manages off-site events for Doist. “It should be 20% work, 30% activities and 50% free time.”

This free time allows the kind of spontaneous connection and conversation that return-to-office apologists have lauded. And it fundamentally alters how — and where — these off-sites are organized.

“Don’t take us to some big hotel in the middle of a city and give us a big itinerary,” Warrington says, channeling employee sentiment.

This might spell trouble for traditional conference centers and hotels that depend on a steady drumbeat of business travel. Yet it has created a new small-business ecosystem geared at helping remote businesses manage employee morale via retreats.

» Learn more: Workcations — should your next trip mix work and play?

Enter the off-site startups

Investment has poured into the budding off-site industry. The software company Salesforce has built a dedicated wellness retreat in the California redwoods in which to hold team-building events. And Workation Village, a custom-designed site in Italy for company retreats, launched in 2021.

Yet remote companies are discovering that, while companywide gatherings with hundreds of employees may help boost morale, they’re a pain to organize.

“Many companies are introducing a travel manager position,” Muchada says. “But they realize that it’s a lot of work to organize everything, and that’s why many companies are contacting us.”

Surf Office manages retreat locations around the globe, from Santa Cruz, California, to Tuscany, Italy, and aims to alleviate the guesswork (and paperwork) for travel managers and human resources teams. Similar businesses are popping up to address this sudden spike in demand.

“When the vaccines started to roll out, I started to recognize that the world is changing,” says Hunter Block, founder of Offsiter, which offers an Airbnb-like marketplace of retreat locations. “People are never going to go back to the office.”

Block quickly realized that organizations needed more than just a location — they needed an organizer. So Offsiter now offers full-service management of everything from catering to collecting T-shirt sizes for company swag.

“We can handle all of it, all the way down to holding the clipboard and telling people where to go,” says Block. “Then, the whole team gets to participate in it, rather than being distracted by the nitty-gritty. We’re very much like a wedding planner.”

Despite its sudden rise, the off-site industry remains in its infancy and has plenty of kinks to work out.

“I’ve tested some tools that are meant to serve this market, but they’re very raw,” Warrington says. “They’re building the airplane as they fly it.”

How to maximize your rewards

You want a travel credit card that prioritizes what’s important to you. Here are some of the best travel credit cards of 2024:

• Flexibility, point transfers and a large bonus: Chase Sapphire Preferred® Card

• No annual fee: Wells Fargo Autograph℠ Card

• Flat-rate travel rewards: Capital One Venture Rewards Credit Card 

• Bonus travel rewards and high-end perks: Chase Sapphire Reserve®

• Luxury perks: The Platinum Card® from American Express

• Business travelers: Ink Business Preferred® Credit Card