How to turn your work trip into a “bleisure” vacation

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Work trips sound like a great idea, but most of them don’t allow any time to explore the city and enjoy the attractions. You’re stuck in conference rooms or in meetings with clients leaving precious little time to actually visit the city you’re in. If you find yourself in this situation, you need to learn about a concept called “bleisure” vacations.

I’ve partnered with the Dosh cash back app to share simple ways to get a personal vacation out of a work trip.

What is “bleisure?”

Bleisure is a concept where you mix business and personal time when traveling. This can be achieved by adding personal time at the front or end of a work trip to create a mini-vacation for yourself.

The 2nd annual National Rent A Car “State of Business Travel” report found that 90 percent of Millennials have engaged in bleisure travel in the past year. But they weren’t the only ones, with 81 percent of Generation Xers and 80 percent of Baby Boomers also tagging on some personal vacation to a work trip.

Reasons to take a bleisure trip

If you’re not sure that a bleisure trip is right for you, there are several reasons why you should plan one:

You’re saving time

Whether you are rich or poor, we only have 24 hours in a day. Time is one of our most valuable assets. Since you’re already in the city, you’ve saved the hours of travel time that you’d waste if you booked a return trip for a future personal vacation.

The flight is already paid for

Your company has already paid for you to be in this city, don’t waste their generosity. Spend a few dollars or hotel points to book your extended bleisure vacation.

You know people in the city

While at your conference, business meeting, or other work activity, use “small talk” to find out great things to do in town. People love to talk about their city, and this is a perfect opportunity to find the best food, uncover hidden gems, or learn how to skip the line at popular attractions.

I started a whole podcast focused specifically on these types of conversations with local experts. Listen to a few of my podcast episodes at We Travel There and to learn what to ask about. You never know, maybe we’ve already recorded an episode about the city you’re traveling to!

How to turn your work trip into a personal vacation

You’re already traveling to a city you’ve wanted to explore, but there’s no time to do so. Mornings are designed to get ready for the day’s meetings and your evenings are either spent with the client or debriefing with your boss or colleagues.

What should you do? You’ve always wanted to visit this city, and now you’re here. Except you aren’t. There’s no way to do both… or is there?

Knock ’em dead at your meeting

First and foremost, remember the reason why you are there. You have to handle your business otherwise the boss will never let you take time off. And if you execute perfectly, close a big deal, or otherwise impress your boss, maybe you’ll be rewarded with a little extra time off to celebrate.

Read: How miles & points can advance your career

And the more that your boss knows that you can perform effectively, the more likely that they will allow you to bend the rules a little to mix business and leisure.

Request vacation time after the trip

An easy way to extend your work trip is to request time off before or after the trip. You could request time off before your trip, but that limits your ability to be fully prepared for your meeting. Even if it isn’t as convenient, request time off after your meetings. That way it won’t interfere with preparation and you can enjoy your time off without any added stress.

Time your meetings to begin on Monday or end on Friday

Most of us don’t work Saturday and Sunday, so timing your meetings to coincide with the weekends is a great way to extend your trip without using your precious vacation days.

Offer to pay the difference in flight costs

If your departure or return flight is extra due to the change in dates, offer to pay the difference. Even if your boss says you don’t have to, it will show goodwill on your part to make that offer.

Fund your trip by booking your hotel using Dosh

Now that you’ve figured out how to extend your work trip into a personal vacation, how are you going to pay for it? Here are a couple of ways that I use Dosh to pay for my extra hotel nights for my bleisure trip.

Paying for work hotel rooms with Dosh’s hotel service

Many corporate jobs require you to use a reservation system like Concur to book your travel. But with so many of us working for a small business or for ourselves, there’s a great opportunity to book using Dosh’s cash back app.

Dosh offers over 600,000 hotels globally at prices that are competitive to Expedia and other travel websites. And you’ll earn up to 40% cash back after completing your stay! Your company gets competitive pricing and you get awesome cash back. Win-win.

Booking personal rooms with Dosh

Even if you can’t book your work trip hotel stay using Dosh, you can still save money by booking your personal hotel reservations this way. Again, you’ll receive competitive pricing with the potential for up to 40% cash back.

Read: What is the best app for last-minute hotels? – Dosh vs. Hotel Tonight

I recommend setting up an online bank account designated for vacations, then transfer your cash back savings into it every month. It’s a great way to ensure that this vacation money doesn’t get wasted on frivolous daily purchases.

Cash back on dining

Sign up for Dosh and register your credit cards for automatic cash back up to 10% when you dine at participating restaurants. Use a credit card that gives cash back for dining, like the Capital One Savor, and now you’re building up a vacation fund to pay for your next trip.

Read: 9 simple tips to maximize dining rewards when eating out

When planning a trip, I use the Dosh cash back app to find new restaurants to try in that city. Not only do I get to try someplace new, I’m earning up to 10% cash back while doing it!

Shopping online through Dosh

I think most people know about shopping portals. Instead of going directly to a website, use a shopping portal to receive cash back, airline miles, or hotel points towards your next vacation. With the Dosh cash back app, you can shop via the app to earn cash back as well.

Read: How to earn up to 13x rewards at Staples

But did you know that you can get cash back for shopping at participating retailers in person? Way more convenient and hassle-free than shopping online… and it’s automatic! For example, right now you can get 5% at Sam’s Club, 3% at Sephora, and 5% at Carter’s.

Redeeming hotel points for your extra nights

Of course, you can always redeem your hotel points for these bleisure trip hotel stays. However, with so many hotel programs now offering 4th or 5th-night free benefits when redeeming points, this may not be a good idea.

If your points balances are running low, I recommend saving your points for the bigger vacations to get the free nights and use cash for the short trips.

The Bald Thoughts

When traveling for work, you have a unique opportunity to squeeze in a personal vacation for very little added expense. Combining business travel with personal leisure vacations is known as “bleisure”. If you’re a good worker, your boss will most likely say yes to your request to extend your trip so you can relax and explore the city. When booking your hotel stay, use the Dosh cash back app to find great rates on over 600,000 hotels globally and receive up to 40% cash back on your stay.

Have you ever extended a work trip to visit a city? What did you say to your boss to get them to approve it? Share your experiences in the comments below.


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