These days, the boundaries between work and leisure have become increasingly blurred, with technology allowing people to work in new, more flexible ways, and to throw out the rigid definitions of the past.

Nowhere is this more evident than with business travel. Where once traveling for work was a fairly dreary affair, all grey motels and unexciting expensed meals, nowadays boss ladies have the ability to work from almost anywhere in the world, making business travel another prospect entirely. If you can code from a hammock in Bali, or visit NYC on a cruise while finalizing a design project, then why wouldn’t you want to make your work trips even more enjoyable?

Millennials are more likely than any other generation to travel for work, and increasingly they are looking to make their work trips more interesting, and put more of a focus on their quality of life and gaining new experiences. Business travelers will often even tack extra days or weeks on to the end of a business trip, turning work into fun and a business trip into a genuine vacation you’ll remember forever.

If you are looking to mix business and pleasure and merge your business travel with something more enjoyable, then read on for a few tips on things to think about when your office asks you to take your next work trip.

Save Money and PTO

Save Money and PTO

One of the great benefits of turning your work trip into a fun trip is saving money. It’s likely if work is sending you on a trip they are fronting the cost of flights. A simple request from your team to extend your stay after the business is taken care of is a great way to take advantage of the flights you have to board anyways. Most employers are willing to make this happen. So ask away lady! You deserve this! 

Most employers pay for your travel time which means time in the air is time saved from your coveted PTO hours. Save the paid time off for exploring the city or driving to the nearest beach to soak up the rays not hours in a stuffy airplane. 

Where to Stay

Where to Stay

Your employer probably will put you up for the night if you are traveling for work, and they’ll have paid a lower corporate rate for your room. Try negotiating with the hotel manager to see if they will let you stay on for the same rate – hotels usually want to develop a good rapport with their corporate guests so it might well be amenable. It never hurts to ask.

If you are organizing your own accommodation and are looking to work while you travel, make sure you book smart. Staying in an Airbnb can be a great option, as you might well be able to find one with a separate study space where you can work, while the family does their own thing. Just make sure the wifi is powerful enough.

Better yet take advantage of the accommodations your employer books with and then move neighborhoods when you’re on vacation. By doing so you can explore multiple parts of a city and really get to know the different areas. 

When to Go

Traveling for work tends to operate on a different schedule than normal tourism, but this doesn’t have to be negative. If you are heading to a conference, it might well be worth extending your stay, as they are usually held in desirable destinations during the off-season. You can take advantage of being sent there on the company dime, then benefit from off-peak prices as well.

It’s also worth paying attention to the individual trends in the cities in which you are traveling. Most places will be cheaper during the week (when you are likely to be traveling for work), but some cities like Chicago and New York are just as expensive on a weekday. Plan smart, and you’ll get more out of your trip.

Pack Smart

When turning a business trip to vacation it can easily turn into an extended itinerary. A 5 day work trip can turn into 10 days away from home. Be sure to pack accordingly. You can save space in your suitcase by packing dresses that can be layered with a blazer for when business professionalism needs to be maintained but for when you are in vacation mode- ditch the blazer for a nifty scarf and moto jacket. Then you’re ready for a night on the town. 

Keep the hair drier at home- most accommodations have one in the room. Pack comfortable flats to double as work shoes while providing comfort when exploring the city on foot.
Another great packing trick I love- compression cubes. No need to say no to your favorite top when packing in compression tubes. They are a great investment, especially if you travel a lot. 

Enjoy Every Minute

For some business trips, you won’t even have to add on extra days to turn a work jaunt into a great experience. Evenings are the perfect time for foodies to explore the cuisine and dining scene in a new city, while a hotel with a spa makes for some stupendous downtime. Be savvy with your time and your work trip can feel like a treat without any extra effort.

Have a friend at work you enjoy spending time with? Invite them along too. This can be a great opportunity to get to know one another better and network in a setting that’s fun and out of the norm.


When traveling for business, don’t be afraid to extend your trip or head out early. Most employers welcome the idea as it’s nothing more to them. If you’re one of the lucky ones who has a flexible work remote policy why not take some half days in a neighboring city. Work from a coffee shop and then pack up your computer and enjoy the sites! This is one of my favorite ways to travel because it helps me see more of places, it’s budget-friendly and it helps me to make the most of my time! I hope these tips help you and encourage you to take more vacation days when it’s safe to travel again.