How To Squeeze A Little Holiday Into Your Business Trip

How To Squeeze A Little Holiday Into Your Business Trip

Business trips are bittersweet. You go to London for a few days, you think that means exploring the city, but nope — you’ve got work to do. It’s still possible to make some time for pleasure, though. It’s not like you want to score a free holiday on the company dime, but with some planning, you can make the most of your business trip and still find time for fun.

Illustration by: Sam Woolley

Prioritise Your Sightseeing

When you’re on a business trip, you typically don’t have much time to yourself. Research is key when it comes to planning any kind of travel, but when you’re on a time crunch, it’s even more important. You don’t want to waste your precious, limited time with unexpected surprises.

Before you go, look up all the fun things to do in that city. Make a list of every sight you’d like to see, from museums to restaurants to shows, then prioritise according to how much time you have. Chances are, you’ll only have time to do two or three things from a massive list, so make those things count. It might even help to set a goal for your holiday: I want to eat like I’ve never eaten in Paris. Or, I want to see some really cool ruins in Rome.

The Lonely Planet’s Guides app (free for iOS and Android) is a great place to get started. It includes 38 different cities and curates information about points of interest, travel tips and etiquette suggestions. You can also bookmark info and save it offline.

Frommer’s is also a great resource to find things to do in a limited amount of time. You can search their site by destination, navigate to Suggested Itineraries and the site will tell you what to do if you only have a day in that city. Of course, expect most of these spots to be touristy. If you know someone who lives in the city or has travelled there extensively, ask them which spots are worth checking out and which are worth skipping. Or, better yet, get their expert recommendations from the start.

Don’t try to cram everything in, either. If you’re travelling for business, you don’t want to feel stressed on your down time. Make the most of it by keeping your leisure schedule light. This way, you can actually enjoy exploring without feeling rushed and crunched for time.

Of course, if possible, it helps to extend the trip and give yourself an extra day for fun after you’ve taken care of business. It will probably be on your own dime, but hey, you still got over there for free.

Find a Hidden Layover City

If you really want to get more out of your trip, and your employer is cool with you booking your own flights, find a hidden layover city.

Find flights with several hour layovers in a stopover city, then leave the airport in that city and do some exploring. Of course, you want to make sure this doesn’t screw up your schedule, but if you don’t have to be at your destination at a particular time, this is a great way to squeeze in some fun.

I sort of did this on a recent work-related trip to North Carolina. It didn’t really matter what time I got in, and I had nothing planned that night, so I decided to take a flight with a three-hour layover in Houston. This way, I could visit my parents for lunch. Seeing a couple of familiar faces made the trip feel a lot more casual and fun until I had to get into work mode.

CleverLayover and Skipplagged are solid tools for finding these hidden cities, but Google Flights will do the trick, too. Search for a flight, and under the “More” tab, you’ll see a list of stopover cities you can select or deselect. If you want to search for all of them, select “Any Connection”.

Maybe you have friends in the layover city, or maybe it’s just a fun stop on the way to your destination. Either way, if you have the flexibility to search for and pick your own flights, this is a simple way to get a little more out of your trip.

Be Strategic About Your Hotel Location

It’s easier to get in some downtime if your hotel is in the right area. Consider your work obligations and the attractions you want to see, then book your lodging accordingly.

You’ll probably spend more time on business, so it might make sense to book closer to your work obligations. Still, it helps to plan all three — work, fun and lodging — in the same general vicinity so you can spend less time commuting to and from everything. More free time for fun!

For example, our own editor-in-chief, Alan Henry, plans his work trips to New York this way. He finds a fun area to stay in that’s a quick Uber ride from the office but is also near some nice pubs and eateries. This way, his lodging is close to the fun stuff but he can still head to and from the office without worrying about spending his time navigating the subway.

On the other hand, if you’re travelling for business, your meetings and conferences are probably in the business district. In most cities, those districts are pretty empty and lifeless at night and on the weekends. Consider booking your hotel in a livelier part of town. This way, you’re closer to all the fun stuff, and when you retreat back to your hotel after work, it feels more like a holiday. If you’re free after a certain day, you could even book two separate hotel stays: one closer to work; the other near the fun stuff.

Schedule Meetings Near Places You Want to See

If you’re meeting with clients or other business-related peeps, get creative with your venue. You could schedule meetings in the same vicinity of your office, but maybe at a more interesting place that’s not just an office park. Or, perhaps you could bring them to your office, then suggest a break and meet up for dinner and drinks in a livelier part of town to finish things up. Meanwhile, you can fit in a show or some sights. Here’s another suggestion from Forbes:

Rather than meeting in a hotel lobby or restaurant, for example, invite a client or colleague to an exhibition you’d like to see. If the relationship is very formal, set up a business meal near the site you want to visit, and go before or after.

It also helps to set some clear boundaries for your schedule. It’s easy for a one-hour coffee meeting to turn into three hours of talking about work or worse, making droll chitchat. Let your clients or colleagues know the meeting has a deadline. And you don’t have to be a jerk about it. You could simply ask, “Are you free for breakfast from 10:00am to 11:30am?” This lets the other person know you have things to do without making it seem like you’re too busy and important for them.

Of course, you don’t want to cut a meeting short just because you want to play in Central Park, either. Pleasure comes secondary during a business trip, but creating boundaries helps protect your limited free time.


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