Many who travel frequently for work know “multi-stop business trip” by another name: business trip.

It’s the rule, not the exception to their mad-dash world of tiny soap and Skyping with family. Sure, technology has made it easier to take care of business remotely, but with business travel still toppling $3 billion a year once all the final expense reports are approved, there is no doubt a sizeable army of mobile movers and shakers. This is the “Up in the Air” existence, where you can recite the flight attendant’s safety speech verbatim and know TSA agents by name.

But what are the best options for managing business trips with more than one destination, and given the choice, does it even make more sense to consolidate trips together or break them up? That airline magazine crossword is likely all scribbled over, so instead feast your eyes below – we have some answers.

Options for Planning Multi-Stop Business Trip

Depending on whether you’re a company employee or a self-employed business traveler, and a whole host of other factors, there are different means of building an itinerary for a multi-stop business trip. Here is a deep dive…

• Travel agents or company resources: Your company might outsource travel to an agency. The good news is that these are more than likely savvy travel experts who will book you the best flights and hotels – for the company. The bad news is that because of this extra layer bureaucracy, these travel arrangements may lack the personal touch you desire. Hey, we understand why left-handed travelers prefer the aisle seat; you shouldn’t have to make a special request every time you go from Toledo to Toronto to Tupelo and back again. Similarly, your company may have an in-house travel department, dedicated administrative support, or simply someone who was unlucky enough to draw the travel booking duties. Unless you have a strong professional relationship with this person or department, we’ve found that people generally put less care into booking others’ flights and hotels than they do their own. Always be sure to double-check itineraries for details, especially for connection times, and the distance between airports, hotels and meeting venues – especially when there is no rental car stipend and you’re depending on public transit or your own two feet. Actually, check everything. I once had an admin switch my destination and arrival cities and also book the wrong day – all on the Daylight Savings change weekend. And my mind is still spinning….

• Going solo: Maybe you’re a daring entrepreneur. Maybe your company is just too… trusting in your ability to book your own itinerary. Trusting, yeah, that’s it. Booking for yourself cuts both ways. You’re more likely to land your airline, seat, hotel and rental car preferences, but you’re also spending all the time to make it happen. On top of that, new airline pricing move really works against those cramming multiple destinations into one business trip. Pricing used to favor multi-destination trips. But in the Spring of 2016, American, Delta, and United raised rates for these trips. Now it’s cheaper – and much more time-consuming and inconvenient – to book a series of separate, one-way fares, called segments. The issue here isn’t just the time suck that gets created with extra booking, but also because you now have a collection of separate reservations, the airline won’t be alerted that one flight’s delay could trigger an issue with another flight. While it’s inconvenient, this strategy of booking separate segments could save you thousands of dollars, especially if you’re juggling international destinations.²

That’s how to book. As for when to book? Eight-five days ahead of your trip is the ideal time, but often not realistic. Aim for at least three weeks out, which can save you up to a third off fares.³ Then there is where to book. Online booking sites continue to grow, evolve and build new niches. Sure, you still have your Orbitz and your Expedia. Then you have a whole bunch of aggregators, such as Kayak and the newer Trivago, which wrangle up airfares and rooms from other sites, carriers and companies. More specialty booking sites, such as HotelTonight for last-minute bookings, are also gaining popularity. Matrix software search, a user-friendly tool designed to help book multi-city business trips, is also popular within the frequent flier community.

• Concierge service: There are a number of concierge services available that can help grease the wheels for smooth multi-stop business trips. CrankyConcierge is a cost-effective online service for planning, monitoring or troubleshooting flights. But what you may not know is that travel insurance providers, such as Allianz Global Assistance, provide knowledgeable concierge services to help optimize your trip or get you out of snags.

The Pros and Cons of Multi-Stop Business Trips

Eliminating one travel leg from each trip can certainly save a ton of time. Why go there and back and there and back, when you can go there to there and then back. Fewer flights mean reduced costs. And streamlined, multi-stop business trips can also mean fewer nights away from home, which not only nets additional savings but also has a work-life balance benefit. No family likes to have mom or dad gone for an extended period of time, but one long trip can be easier to schedule around than multiple short trips.

But let’s be honest. It’s not all peaches and sunshine when you’re on the road for a week, in a different city each night. Red-eye flights, different mattresses, early wake-up calls and stressful connections can wear you out, physically and mentally. And that doesn’t even include the stress of high-stakes business meetings and contract negotiations.

One way to help stay at your freshest when big business meetings loom? Micro-hotels. These private, tiny rooms and work stations allow travelers to catch some sleep or catch up on work and life. At Dallas-Forth Worth, Philly International and Atlanta / Hartsfield’s international airports, you’ll find Minute Suites, one of a number of chains in the growing space.⁴

Another potential challenge of multi-stop business trips is ground transportation. Renting one car in on city can be enough of a pain, but managing transportation between airports, hotels, meeting sites in multiple destinations can be time-consuming and tricky. Don’t rule our ride-sharing services such as ZIPcar and popular app-enabled car services Uber and Lyft as opposed to traditional rental cars. You’ll get more flexibility, especially if something goes awry.

Here is the elephant in the room regarding multi-destination business trips. It only takes one cancellation, delay, lost bag or other unplanned events to send your plans spiraling out of control. It’s the first domino in a chain of unfortunate events that undoes all your planning and preparation. That, of course, if where travel insurance can help. Not only do benefits for trip cancellation, delays, and other circumstances provide a financial recourse for business travelers, but the aforementioned concierge benefit can help get your trip back on track before it comes off the rails. With travel insurance, the risk-reward of these multi-stop business trips becomes much more weighted to the reward.

A multi-destination business trip is a bold move. Done right, it can boost your business by saving time, money -- and actually promoting work-life balance. But there are risks that such aggressive trip planning is prone to – risks that travel insurance goes a long way to mitigate. So pack your bags, bring some extra deodorant and print out that sprawling itinerary. It’s time to zig-zag your way around the world to success.

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