
Tired of flying across the country or even halfway around the world for business meetings, only to fly right back without seeing anything beyond the airport, your hotel room and the office?
What if those corporate trips could be more than just work? At Sidewalk Safari, we advocate for the part-time travel lifestyle, a way of traveling where your full-time career unlocks personal travel opportunities you never could have dreamed of alone.
Bleisure Travel is a savvy way to transform your business trip into an adventure. The trip is centered around your work and at least partially paid for by your “day job,” but imagine extending your stay, exploring a new city, or even bringing a loved one along.
I live by the motto: “Work to Live, Live to Travel, Travel for Work,” and have honed my bleisure craft over the last 20 years, evolving my career in a direction that could fuel my passion for travel and living in different places.
Ready to transform your next business trip into a legit bleisure experience? Here are my top 10 tips to turn business to bleisure that will change how you think about business travel for good!
1. Fly in Early
Fly in on the first flight of the day before your business begins to get the most time on the ground.
2. Fly Out Late
Fly out on the last flight the day after your meetings end to get the most out of your trip at no additional cost.
3. Get Up Early
Get up early and go for a coffee walk. You can sleep in once you are home.
4. Explore Before Dinner
Take a walk around the area before going out to eat.
5. Accept Invitations
If your coworkers suggest going out, say yes. Locals know the hidden gems of the area.
6. Go to a Meet-up
Meet-up.com is an excellent way to connect with locals and an excuse to check out cool venues.
7. Stay the Weekend
You will have to pay for the extra time yourself, but your flights are already paid for so the trip is still subsidized.
8. Make It a Workcation
Spend an additional week (or 3!) at your destination.It’s not as costly as you may think because your flights are already paid for.
9. Bring a Friend
Bring a friend or your family. They can stay in your hotel room for no or little added cost.
10. Take an Expat Assignment
Love traveling for business and want to keep it going for a longer period of time? Look for job opportunities abroad to become an expat to live a full-time bleisure life. That’s what I’ve done since 2010, working from Ireland and now Portugal to maximize my travel opportunities.
Your Printable Business to Bleisure Checklist
Download and print the Sidewalk Safari business to bleisure checklist so you don’t forget to seize the opportunity the next time a business trip comes your way.
Bleisure Travel Inspiration
Check out bleisure travel in action with these write-ups of business trips that I supercharged with some fun activities.




