Advice for frequent business and pleasure travelers that I wish I'd been given years ago

I'm looking towards next week, the eleventh (and final) straight week during which I will have flown somewhere for either business or pleasure. It's actually been a great run, at the end of which I find myself reflecting on the lessons I've learned since a new job served as my first foray into the world of frequent travel about ten years ago. I've traveled often since I was a kid, but in recent years I've picked up five notions that help me to still keep travel fun. This is the advice I'd give to adventure seekers and business travelers taking to the skies on a more regular basis.

Sometimes it's OK to be a bit of a tourist. I stopped for BBQ on Beale Street in Memphis, Tennessee while traveling on business two weeks ago.


Every trip is a chance to experience something different, drink something great, and meet someone new.

This one is easy when you're off to notable places, but there are plenty of great reasons to travel in places other than Paris. In just the last two years I've tasted at a winery in Arizona, enjoyed a world class dinner in Kansas City, drank a sparkler on the terrace of a gem of a little restaurant in Fayetteville, North Carolina (yes), and -- just two weeks ago -- actually gone walking in Memphis. These four occasions in particular hold in common that I was, on each, traveling on one piece of business or another. It's easy to get bogged down in frequent or last-minute business travel to random places, but you'll be amazed at how your outlook (and your work ethic) changes when you re-orient yourself and remember that you've a chance for a new experience on every trip.

Further reading: Touching down in Phoenix for a little taste of Arizona wine and absolutely beautiful country

Create a system.

Clearing that mental barrier is half the battle, but physical barriers await, and packing intimidates. I'm on a really short turn right now, having flown home from Florida on Sunday, off to North Carolina on Wednesday, back to Virginia on Thursday, and off again for Labor Day weekend with family on Cape Cod tomorrow. I can do that (relatively) stress free because rather than facing a monumental packing task each time, all I'm really do is executing a pre-defined process each time I gear up to head off. I know exactly what I need for each single day of travel, I've pre-staged (in a single TSA-approved toiletry kit, electronics bag, travel wallet, etc) as much of it as is feasible, and I know exactly where everything fits in my suitcase. I've also long-ago spent a little bit of time on a checklist that I re-use every time, and I tweak that checklist whenever I learn a new lesson.

Further reading: Review: Great Tumi Alpha 2 International Carry-on suitcase fits 17 days of stuff into the overhead bin

Invest in gear that is versatile, durable, and small.

Think of travel as a sport. Just a serious athlete would invest in the right skis, golf clubs, running shoes, bicycle (or whatever your sport calls for) to perform their best, you the serious traveler must also invest in the right hardware to enable your system and keep you performing at your best. I learned this the hard way one hot summer day in 2007 when my the handle on my cheap suitcase disintegrated as I lugged it up the steps of Madrid's Antón Martín metro station (that trip's final days were not pleasant). The trick is to seek out travel gear that you can use in multiple scenarios -- business and pleasure, warm climate and cold, airplanes and rental cars, etc -- that will hold up to whatever situation you (or the baggage handlers) throw it in, and is small enough to help you avoid the need for ever relying on those baggage handlers. Whether it suitcase, toiletry kit, laptop bag, portable battery, or whatever else keeps you running hard without worry for your stuff... make the investment to go the distance.

Further reading: WTF Travel Shop (thanks for supporting Wine:Thirty Flight!)

With bustling hubs in Boston (pictured) and New York, jetBlue is a great airline choice for those whose travel plans have them frequenting the northeast of the United States.


Pick an airline, and fly it whenever possible.

I've written about this before, but suffice it to say, the more you fly on an airline, the better (in general) your experience on that airline will be. Pick one that works for you based on where you live, where you're going, and what you value in a travel experience. Then concentrate your flying on that one airline so that you earn higher tiers of status that unlock some combination of free checked bags, better seats (or even upgrades to business or first class), and all around better service. Maintain a membership to their lounge (sorry, but jetBlue and Southwest have no lounges) to relieve further stress (and drink complimentary house wine) while in the airport. Your choice is pretty simple of you live in a city dominated by a single airline, but those with options should put some thought into where you're going most of the time. For example, Delta (hubs in Atlanta, New York, and Boston), American (hubs in Miami, Charlotte, DC, Philadelphia, and New York), and jetBlue (hubs in Ft. Lauderdale, New York, and Boston) are really solid on the east coast of the United States. United (hubs only in DC and New York) less so. The less obvious reason to embrace this approach is that organizing your travel around airlines with strong networks in the regions to which you most often travel permits you access to alternative flights when yours is delayed or cancelled, a benefit that the low cost carriers Spirit and Frontier just can't offer (also the experience on those airlines is miserable).

Further reading: How (and why) to choose your preferred airline

Go to the gym.

I cannot overstate how unhealthy most of us are when we eat on the road. I've worked really hard this year at packing my workout clothes, and then forcing myself to go to the hotel gym. My performance on this count is not saintly, but developing and maintaining this as a core discipline of your travel routine is so important for staying healthy, keeping your energy up, and maintaining your daily rhythm. Think of it as the price you'll gladly pay for the great food and wine you're planning to discover along the way.

Happy travels this (in the United States) long holiday weekend!