How to travel multiple times a year while working full-time (or running a business)

And no, I'm not a full-time digital nomad.

If there's one thing I think my family judges me for, it's the money I spend on flights (kidding, I know it's my fashion sense). Jokes aside, one of the questions I often get asked — if not outright — is how I afford to travel.

Truthfully, there are a lot of factors that go into my lifestyle, but what it comes down to is I make work work for me because being able to travel often is my priority. Here are some ways you can make travel work for you as a remote worker, while still paying rent.

First, prioritize.

The key to traveling often is deciding what trips are your priority.

Unfortunately, no matter how much FOMO you have, you can't say "yes" to everything. How do I prioritize, you ask? I typically pick one trip to be my "big spend" for the year. On this trip, I don't intend to work at all — it's more of a vacation, of sorts.

Based on my budget for this one big trip, I typically choose one other major destination I can finagle my way into via work or academia. That said, I try to make work or academic trips happen, with the justification that it's good for my career (Bonus: if you own your business, you can probably write some of these trips off — consult your accountant!).

Taking several international trips a year is glamorous, but it isn't the norm for most people, and I wouldn't say it's the norm for me, either. As someone who loves to travel internationally and has all six continents (yes, you heard me, I'm not going near Antarctica) on my bucket list, I would love to take 6 international trips a year, but that's not going to happen for me until I'm making "eff you money."

Every year, I pick one place I know I'd forgo all others to go. I'm not spoiling 2026's pick just yet, but 2025's pick was Montreal. I knew I wanted to visit a friend who lives there, and I had never been. From there, I was able to decide what I was and was not able to afford or do as additional opportunities came up. For me, this usually means one (or two if I'm lucky) international destinations alongside several domestic destinations in a year.

If you can, travel for work.

I get it — this isn't the most realistic option for everyone. But with that acknowledgement on the table, keep in mind that you don't have to work in sales to be able to travel for your job.

I work in comms, so I know firsthand that the "it" strategy right now is for companies to put their employees on a pedestal. Are you an expert in something? Pitch yourself to your company's marketing department — they just might be in need of an expert panelist at an upcoming conference. This exact strategy got me to a couple of different cities in the span of less than a year, including both Austin and Chicago. As a bonus, I got to collect miles on both trips.

Alternatively, you could potentially see if your company is willing to invest in sending you to a conference or workshop. The worst they can say is no, and you get the brownie points for showing interest.

Use your work schedule to your advantage.

When I'm traveling, I'm often working, too. There's a lot you can squeeze in around your working hours, especially if you're lucky enough to be able to flex your working hours.

I have done both, but regardless of how rigid my schedule is, I've been able to see and do plenty. Here are my tips for making the most of your time around your working hours:

• Travel at early or late times in the day; just make sure you know how you're getting from the airport to where your staying. The pros? These flights are often cheaper, but I personally choose to shell out for a taxi if I'm arriving late or know I need to be on a call within a certain time frame after landing.

  
  

• Maximize your time zone. If I'm in Europe, I often take advantage of the time difference to knock out focused work in the morning and sight see just before or right after lunch. Then, I knock out a few hours of calls until dinnertime and I'm ready to do it all again tomorrow. On the west coast, I keep my Eastern Time hours to free up my afternoons. The best part about this strategy is you often cooincidentally manage to avoid the crowds while sightseeing, because you're avoiding peak times on weekdays.

  
  

• Don't feel the need to rush. This piece of advice is twofold. First, be willing to stay in one place longer than you think you should if you're working. When it comes to the actual travel itself, instead of rushing to your destination, consider taking a train. It's easy to knock out some work during the workday, and the trip usually comes with a few gorgeous views. Just be wary — you may not want to plan major calls while you're on the train, because you could lose cell service or experience spotty wifi at times.

  
  

• Plan trips around long weekends. This isn't novel advice, but plan your remote work days (if you're hybrid) or your travel around long weekends. Then, you can cushion the weekend with one or two days of leave to get yourself 4-5 days in any given place.

Be open-minded.

Bonus points: San Diego came with major puppy snuggles and fresh eggs from the chickens on their property every morning.

Travel doesn't always have to look like getting an Instagram-worthy Air BnB somewhere — sometimes it looks like housesitting for a friend.

You'd be surprised, but buying someone a plane ticket is often cheaper than boarding a pet (or, it was before the U.S. bombed Iran, anyway). In fact, there are people who travel exclusively this way — they trade house or petsitting services for lodging all across the word (disclaimer: I haven't tried any of the sites setting up these exchanges myself, but if I do, you'll hear about it).

I've definitely taken friends up on a trade before: Fly me out and let me stay in your house, and I'll watch your dog and/or cat for the price of the ticket. That's how I managed to visit San Diego for 10 days last year (shoutout to Dan, if you're reading this!), and most recently, paid for my trip to Tennessee for my nephew's graduation. Be sure let your friends and family know it's something you're willing to do — some people won't think to take you up on it until you offer.

Double up.

When it comes to traveling to multiple places a year, it helps to piggyback from one destination to another.

This one probably goes without saying — but once you're in a general location, it's easier to get to and from other places close by. See if you can extend your travels by 2-3 days to add a pitstop destination. Take a day trip beyond the main city you're staying in. Plan a train route. There are a lot of ways to make it happen!

Finally, be flexible.

You can take advantage of all of the above, but ultimately, the thing that makes traveling multiple times a year possible is flexibility.

If there's one thing I've learned from years of travel while juggling multiple jobs, it's that the journey is just as important as the destination, and sometimes it feels a little unconventional in the moment.

Ultimately, my attitude over the last five years has been "I'll make it work," and I have. Sometimes, it means traveling on weird days or at odd times. Other times, it means planning which adventures to haul my backpack around on, so I can jump on a quick call between museums. Often, it looks a little outside the box.

Remember: This is real life.

The best gift that traveling while working has given me is perspective. When I started this journey five years ago, I was a little self conscious — were people judging how much stuff I haul around? Do I look ridiculous pulling two laptops out of my backpack at TSA? (Objectively, yes.) Should I be documenting or journaling more? Am I doing this the "right way"?

But what I learned while pulling both of those laptops out of my bag at airport security and hauling a checked bag across cobblestone is that they only "right" way to travel is the way that works for you.

So just remember: Not every trip has to look like Instagram. What matters is that you got away from the desk in your living room and learned a little bit more about the world outside of your home town, if only for a few days.