Blending work and wanderlust is the smartest travel hack no one’s talking about.
Squeezing adventure into a business trip used to be a luxury for the lucky few. Now, with remote flexibility and shifting work attitudes, more people are turning work travel into a piggyback vacation—and employers are surprisingly chill about it. The buzzword? Bleisure. It’s not just a fun mashup of “business” and “leisure.” It’s a whole strategy for hacking your way to subsidized travel without looking like you’re slacking off.
Pulling off a successful bleisure trip means knowing where the company wallet ends and your own budget kicks in. With a few clever tweaks, you can extend your stay, see more of the world, and maybe even sleep in a way cooler hotel than you’d book yourself. Done right, your boss foots the bill for half the journey, and you return with more than meeting notes—you get memories, too. Here’s how to work the system like a pro.
1. Choose destinations your company already needs you to visit.
The easiest way to blur business and leisure is to start with a trip your boss wants you to take, as stated by Sarah Amsler at TechTarget. If your company sends people to conferences, client sites, or satellite offices, that’s your opening. These aren’t random jaunts—they’re pre-approved expenses, which means you’re already on their dime for flights, hotels, and per diem. You just have to be smart about the timing.
Once the work part’s nailed down, you can tack on extra days—before or after the official schedule. As long as the business justification is solid and your work deliverables are handled, most managers won’t blink at a little personal extension. Just make sure it’s clear you’re covering your own leisure time, and you’ll avoid awkward budget questions. That way, the company handles the cost of getting you there, and you turn it into a mini-vacation with zero extra airfare.
2. Plan your personal days around weekends or holidays.
If your business trip ends on a Friday, staying until Sunday doesn’t raise eyebrows—it just looks efficient. Tacking personal time onto a weekend gives you two bonus days without eating up vacation time. Even better if a public holiday lands nearby. Stretching a business trip into a four- or five-day getaway becomes easy when the calendar works in your favor, as per Tom Hardej at Ramp.
You still need to be mindful of the optics. If you’re sipping daiquiris while your coworkers are grinding through Monday meetings, be sure your work was fully handled before you left. Keep things professional and transparent. Nobody cares that you stayed in Miami for the weekend if the client presentation rocked and you responded to follow-ups promptly. Use weekends and holidays like a bridge—connect your professional obligations with personal adventure, and enjoy the best of both without raising a single HR flag.
3. Book flights that serve both work and fun without raising flags.
Here’s the trick: book your flights to serve both purposes, but keep the business needs as the primary reason. Say the company approves you flying out Sunday night for a Monday meeting—nothing’s stopping you from flying out Friday instead, so long as you cover the difference in airfare. If the price is the same or less, most companies are fine with it, as reported by the authors at BBC. Just keep it clean in the paperwork.
You don’t have to over-explain, either. A simple, “I’m flying in early for personal time—no cost to the company,” usually satisfies accounting. What matters is transparency. You’re not sneaking around, just managing your time smartly. And hey, this gives you two whole extra days to explore, unwind, or even scope out spots to return to later. Just make sure your travel choices look responsible on paper, and you’ll be golden.
4. Use your per diem to eat like royalty during the workdays.
Per diems are the unsung heroes of bleisure travel. If your employer gives you a flat rate for meals and incidentals, you’ve got wiggle room to upgrade your dining experience. Pick a place with a tasting menu, grab a few fancy breakfasts, or enjoy a nicer-than-usual lunch—you’re still working, so these meals fall under reimbursable expenses.
But don’t blow it all at once. If you pace yourself, you can stretch those funds across the business portion of the trip and save your own money during your extended stay. The key is to treat the workdays like a gourmet sampler and use the fun days for simpler meals. This balance lets you experience more without guilt. It’s not about being sneaky—it’s about using the perks you’ve already earned to enhance the whole trip. Food’s a huge part of travel joy, and your company might just cover the best parts.
5. Pick hotels that mix business class with personal comfort.
If you’re allowed to choose your hotel, this is where you can really shine. Select a place that fits the company’s travel policy but also gives you that vacation vibe. Maybe it’s a business-class hotel with a rooftop pool or one close to attractions you plan to visit later. As long as it ticks the company’s boxes—location, cost, reliability—you’ve got some freedom to make it your home base.
The bonus? You only pay for the leisure days. During the business portion, your company picks up the tab, and you simply extend the booking. Sometimes you can negotiate a better rate for staying longer, too. It’s a subtle move that turns a dry hotel stay into a mini escape. You’re not being shady—you’re being strategic. Comfort matters, and if you can blend efficiency with ambiance, you’ll return more refreshed than frazzled.
6. Use company Wi-Fi to squeeze in sightseeing breaks.
Not every business trip demands wall-to-wall meetings. Sometimes you’ve got hours of solo work or virtual check-ins. Use those moments wisely. Knock out tasks in the morning, then sneak out for a walking tour, museum stop, or local lunch. Just keep your laptop handy and your phone charged. As long as you’re responsive, no one’s tracking your footsteps.
This kind of flexible rhythm is perfect for bleisure. You’re still delivering on deadlines, but you’re also making the most of being in a new place. The trick is knowing when it’s okay to unplug and when you need to be plugged in. And honestly, a quick morning hike or sunset stroll makes you more energized when you log back in. It’s not slacking—it’s optimizing your environment. You’ll still get the job done, just with a better view.
7. Schedule meetings near must-see spots.
Got control over the meeting location? Pick one that sets you up for fun. If you’re heading to a city with a historic center, cool art district, or beach strip, push for a client lunch nearby. When the meeting wraps, you’re already where the action is—no extra Uber, no wasted time.
It’s a smart way to fold in a little tourism without feeling sneaky. You’re not ditching responsibilities, just aligning your schedule with intention. Even if the visit is brief, it can change the tone of your trip. You’ll feel like a traveler, not just a suit. And sometimes that small detour turns into the highlight. Just remember to keep it professional while you’re on the clock. Snap photos after the handshake, not before. That way, you’re fully present for the meeting but still soaking up the perks of being in a new city.
8. Extend your stay and work remotely from your hotel.
This one works like a charm if your boss is already cool with remote work. After your in-person duties are done, offer to stay a few extra days and work remotely—on your own dime, of course. You’re not asking for vacation, just continuing your job in a different setting. And since you’re already on location, it’s not much of a leap.
Many managers will agree, especially if your output stays strong. You can check emails by the pool, hammer out reports from a café, or handle calls from a breezy balcony. It’s still work—but it feels different. You’re sneaking a bit of leisure into your routine without needing PTO. This blend is what bleisure is all about. You’re not ghosting, you’re just relocating temporarily. Just be sure your internet’s solid and your focus stays intact. Nothing ruins a good thing like spotty Wi-Fi or a missed meeting.
9. Volunteer for trips others don’t want.
Some destinations don’t spark excitement—think industrial towns, freezing winters, or off-season visits. That’s where you swoop in. Volunteer for the unglamorous travel, and then make it your own. If no one else wants to go, you’re more likely to get approval. And once you’re there, you can extend the trip to somewhere nearby that’s way more fun.
A little research goes a long way. Maybe the boring business hub is just a train ride from a vibrant city. Or maybe the off-season means lower hotel rates and fewer tourists. Either way, you turn a “meh” assignment into a stealthy adventure. Plus, your boss sees you as a team player, which never hurts. The less popular the trip, the more wiggle room you often have to shape it to your advantage. Bleisure is about being opportunistic—and this is the definition of working the angles.
10. Ask your boss directly—many are surprisingly supportive.
This one feels risky, but it can be the most effective. Just ask. Frame it right: “I’d like to extend my trip for personal time, at my own expense. Would that be alright?” Most bosses appreciate transparency, and many will say yes if it doesn’t affect your performance or cost the company extra.
You’ll be surprised how supportive managers can be, especially if you’ve built trust and handle your workload like a pro. The key is tone and timing. Ask before the trip, not after, and make it clear you’re not expecting reimbursement. This shows you’re thoughtful and proactive—not trying to game the system. Sometimes, they’ll even offer tips or flexibility you hadn’t considered. Honesty opens doors. You might not just get approval—you might get insight into how others in your company do it too. Bosses like people who think ahead, and this move proves you’ve got the chops.
11. Turn your presentation or event into a passport to other cities.
Got a keynote gig or a multi-day seminar in one city? That’s a launchpad. Once your duties are done, you’re free to move on to another city—especially if you’re already close to a destination you’ve been dying to see. You’ve already flown out and settled in, so why not keep going while you’re in travel mode?
Use company-paid airfare to land near your dream spot, then book onward travel yourself. You might have to shell out for a train or budget flight, but it’s still cheaper than starting a trip from scratch. You’re saving time, too—because you’re already halfway there. The key is keeping the business portion tidy and separate. Deliver what you promised, then disappear into your next adventure without dragging the company along. Bleisure isn’t about blurring lines—it’s about dancing right on the edge and making it work beautifully.