After spending a summer looking at your friends’ and colleagues’ vacation photos on social media, you might be itching for a little time away yourself.



For busy small business owners, a two-week trip to Europe may be out of the question. Just 9% of small business owners surveyed by OnDeck say they take two-week vacations. But that doesn’t mean you have to go without any R&R. More than half (57%) of small business owners surveyed plan to take a vacation of some sort and combining business and leisure on a long weekend trip is a great way to get the best of both worlds.


Here’s what you need to know to make the most of your get away.


Look for a destination with plenty to offer. Is there an industry convention coming up in Hawaii or New Orleans? Do you have a client in New York City or San Francisco? If so, see if you can’t combine a business trip with some time off in one of these popular vacation destinations. If you’re planning to bring your spouse or children along, make sure there will be activities to occupy them during the times you’re meeting with the client or attending your business events.


Plan ahead. For many small business owners, the idea of completely unplugging from their businesses increases panic. If this is you, you’re not alone: more than two-thirds of the business owners in the OnDeck survey say they check in with work at least once a day while  on vacation. A trip that combines business and pleasure gives you the perfect excuse to relax a bit while still checking your emails. On the other hand, if you do want to enjoy some real downtime, make sure your team back at the office is prepared to handle things during the days you’ll be vacationing.


Keep good records of your expenses. Some of your business travel expenses may be deductible, including the cost of transportation to and from your destination, lodging, meals, tips and taxis or other transportation at your destination. In order to claim these deductions, you’ll need to keep careful records and separate business from personal expenses. Shoeboxed is a great, simple app to scan, digitize and organize your receipts.


Know the tax laws. In order to be deductible, your travel destination has to be outside your business’s “tax home” (the city where your business is located) and the business purpose of your trip must require an overnight stay. Any expenses you deduct for business must be considered “ordinary and necessary” and directly related to your business.

In order to deduct any part of your trip as business travel expenses, the business portion of your trip has to be longer than the vacation part. A day counts as a business day if the majority of your time during business hours are spent on business purposes. Traveling to or from the business location also counts as a business day; so do weekends if they are in between two days that are devoted to business. This makes a Friday to Monday trip a perfect way to maximize your deductions and your downtime, as long as you conduct  business on Friday and on Monday.


The IRS has strict rules for what you can deduct as a business travel expense, and recent tax law changes have affected many formerly allowable deductions. Visit the IRS website for more on deductible business travel expenses and talk to your tax professional before making travel plans.


As busy entrepreneurs, we all need time to rest and recharge to keep our businesses functioning at peak performance. Combining business with pleasure over a long weekend can help you re-energize while growing your business. What could be better?


About Rieva Lesonsky


Rieva Lesonsky Headshot.png

Rieva Lesonsky is CEO and Co-founder of GrowBiz Media, a custom content and media company focusing on small business and entrepreneurship, and the blog A nationally known speaker and authority on entrepreneurship, Rieva has been covering America’s entrepreneurs for more than 30 years. Before co-founding GrowBiz Media, Lesonsky was the long-time Editorial Director of Entrepreneur Magazine. Lesonsky has appeared on hundreds of radio shows and numerous local and national television programs, including the Today Show, Good Morning America, CNN, The Martha Stewart Show and Oprah.


Lesonsky regularly writes about small business for numerous websites and for corporations targeting entrepreneurs. Many organizations have recognized Lesonsky for her tireless devotion to helping entrepreneurs. She served on the Small Business Administration’s National Advisory Council for six years, was honored by the SBA as a Small Business Media Advocate and a Woman in Business Advocate, and received the prestigious Lou Campanelli award from SCORE. She is a long-time member of the Business Journalists Hall of Fame.


Web: or Twitter: @Rieva

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Bank of America, N.A. engages with Rieva Lesonsky to provide informational materials for your discussion or review purposes only. Rieva Lesonsky is a registered trademark, used pursuant to license. The third parties within articles are used under license from Rieva Lesonsky. Consult your financial, legal and accounting advisors, as neither Bank of America, its affiliates, nor their employees provide legal, accounting and tax advice.


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