Summer is never long enough to get in all the traveling you'd like to do. Destinations near and far are beckoning, but you have plenty of work to do back at the office.

That's why some entrepreneurs choose to mix business with pleasure and host a company meeting on the road. They kill two birds with one stone: taking a needed break from the daily grind and getting a necessary business task completed, too.

But having an out-of-town meeting isn't for everyone. Is it right for your business?

Bringing Your Team Together

"Boost Software has both quarterly and annual meetings that are conducted on the road," says Amit Mehta, CEO and co-founder of the Boston-based software company. "In the past, we've taken a small team of core employees from Poland, Italy, Florida, Arkansas, Utah, South Carolina, Vermont and Massachusetts and met up for quarterly meetings in New Hampshire resorts, Poland and downtown Boston."

For the third quarter of 2014, Boost is planning a trip to the Massachusetts coast. "We've found that renting a house has a higher value," Mehta says. "Meeting spaces are included in the house, and there are plenty of rooms so that no one has to share a room. All of that, and the cost is lower than staying in a hotel or resort on the northeast coast. We'll have food catered and brought in, which also offers a savings compared to eating out."

And the trips just get better for the staff at Boost Software. "Our fourth-quarter meeting will be in Bermuda," Mehta says, "and employees are allowed to have two family members come along."

Many of the employees who work for Boost telecommute, so management considers the quarterly meetings a key opportunity to rekindle enthusiasm for the business and encourage camaraderie when the team's no longer separated by miles.

Unnecessary Expense?

Just because you can plan a destination meeting, should you? Michael Claes, founder and executive vice president of Nicholas Consulting, says he advises clients against creating these kinds of trips for a company's annual meeting.

"For most companies, annual meetings are an expensive undertaking that they wish to avoid," Claes says. "The technical and legal business can be accomplished in minutes, and shareholder votes are tallied before the meeting gets underway except for those who actually show up. Typically, and increasingly, annual meetings are sparsely attended. In fact, some companies opt for destinations—sometimes a plant or facility site—that's intentionally inconvenient."

If you're really committed to holding an off-site meeting, then Claes suggests companies follow this advice: "Wherever the annual meeting is held, there must be a company rationale to the destination," he says. "For example, maybe the company is headquartered there." 

It's unlikely that you'll be able to deduct the expenses of a destination meeting. The tax code is clear that business-related entertainment expenses can only be deducted if the expense was ordinary and necessary. In fact, the IRS goes to the trouble of mentioning how hunting and fishing trips as well as trips on yachts or pleasure boats all fall outside the realm of entertainment with a business focus.

An Investment and a Reward

Deduction or not, some small-business owners are enthusiastic about taking their meetings on the road.

"I've been wanting to try a destination meeting. I think it would be a great investment in my team and can create an environment for fresh ideas to help move my business forward," says Kisha Mays, CEO of Just Fearless, a company devoted to empowering, inspiring and educating women and young girls.

"I'm planning one for January 2015," Mays says. "It might be as simple as a five-star beachfront hotel in Ft. Lauderdale, Florida, or something more exotic like a trip to Maui or Fiji. Regardless, it will be a combo business and leisure trip where we'll have the annual meeting and team activities, and offer individual activities.

"I believe the return on investment will be significant," Mays says, "and my team is worth it—thanks to their hard work, focus, efforts and creativity, my business is growing at an amazing rate."

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