Remote Work and Travel: How to Work From Anywhere With Your Family
TABLE OF CONTENTS
Why Mix Work and Travel When You Could Just Take Vacation?
Planning Your Work and Travel Adventure: The Strategy Most People Miss
The Weekend Sandwich Method
How to Actually Work and Travel (Without Going Crazy)
Finding the Perfect Stay for Travel and Remote Work With Family
Adjusting Your Work Schedule - The Flextime Advantage
Kid Management While You're Working
Tech Setup for Successful Work and Travel
My Portable Office Must-Haves
Blending Work Days and Vacation Days: The Hybrid Approach
For Work Days
For Vacation Days
The Art of Disconnecting When It's Family Time
The Economics of Work and Travel: Why It Actually Makes Sense
Is Travel and Remote Work With Family Right for You?
Final Thoughts on Mastering Work and Travel
So you're sitting at your desk for the millionth day in a row, scrolling through photos of tropical beaches on your lunch break, when suddenly it hits you – "Wait, I work remotely... why am I not working from THERE?!"
Honestly, I had this exact same realization, and let me tell you, figuring out how to blend travel and remote work with family has literally been life-changing for us. And I'm not talking about becoming full-time digital nomads (because, hello, school schedules and soccer practice!), but actually taking your regular remote job on vacation with you!
Why Mix Work and Travel When You Could Just Take Vacation?
Okay, I know what you're thinking – "Why would I work during vacation time?" But here's the deal – when you blend work and travel, you can:
Stretch your precious vacation days wayyyy further (I'll explain how!)
Experience living in destinations instead of just visiting
Show your kids different environments while maintaining routines
Save those vacation days for when you really need them
Avoid that "OMG I have 500 emails" post-vacation stress
Last year, I took my family to Boracay for a week but only used ONE vacation day! We still had amazing beach time, incredible food, and made so many memories. How? By being strategic about when and how I worked – and I'm literally going to share all my secrets with you.
Planning Your Work and Travel Adventure: The Strategy Most People Miss
So here's the thing about planning a workation (work + vacation, get it?) – it's not just about finding a place with good WiFi, although that's obviously super important. The game-changer strategy is actually calendar manipulation.
The Weekend Sandwich Method
When we went to Boracay, we planned our trip to include TWO weekends, which immediately gave us four days of free time without touching our vacation days! Then we strategically used just one vacation day (Friday) to create a three-day weekend.
So our schedule looked like this:
Saturday & Sunday: Full vacation days (with half the day traveling to our destination)
Monday-Thursday: Work remotely during mornings, explore in afternoons/evenings
Friday: Used a vacation day
Saturday & Sunday: Full vacation days (with half the day spend going home)
BOOM! A nine-day trip with only ONE vacation day used. That's literally the hack that changed everything for us.
How to Actually Work and Travel (Without Going Crazy)
Look, I'm not going to sugarcoat it. Working while your family is at the beach can sometimes feel like... well, work! But I've done this multiple times now, and I have some real-world tips that I've learned the hard way so you don't have to.
Finding the Perfect Stay for Travel and Remote Work With Family
Your accommodation can make or break your work and travel experience. Trust me, I know. We’ve made a few mistakes earlier on. When we went to Boracay, we specifically looked for a place that had:
A kitchenette with cooking supplies (saved SO much money and time)
Strong, reliable WiFi
A big space that both me and partner can have working space
Extra amenities like a pool (for those post-work swims!)
We found a hotel that had all this, plus it was close enough to the beach that I could occasionally eat lunch with my feet in the sand!
I'm not very tech savvy with booking sites, but I've found that filtering for "apartment" or "suite" usually gives you more options with kitchens.
Adjusting Your Work Schedule - The Flextime Advantage
If you have flextime at work (and if you don't, maybe ask for it before your trip?), use it strategically during your travel and remote work with family adventure:
We chose to start working super early (like 6am) so we could log off by 2-3pm
This gave us the entire afternoon and evening for beach time and activities
My partner and I alternated between lunchtimes so one of us could always manage a total of 2 hours of lunch (or fun time) with our son
This schedule adjustment was honestly such a game-changer because we got to experience sunset on the beach EVERY SINGLE DAY of our trip, even on workdays. We love this. Plus, Boracay really comes alive during this time, less sunburn as well.
Kid Management While You're Working
Okay, so what about the kids while you're trying to work? This was honestly my biggest worry before trying work and travel, but we figured out some solutions:
Pack a special "work time" activity box with new items they haven't seen before
Download offline games/shows for emergency entertainment
Set clear visual timers so kids know when work time ends
Schedule video calls during their natural rest/quiet times
Tag-team with your partner for important meetings
Consider booking a place with a kids' club for occasional use
I brought a bunch of new coloring books and activities for my son, and honestly, the novelty of being in a new place kept him pretty entertained. The rooftop pool was also a lifesaver for those times when the kids get bored.
Tech Setup for Successful Work and Travel
So this part is super important and something most blogs don't talk about enough. When you're planning to work and travel, your tech setup needs to be reliable but also portable!
My Portable Office Must-Haves
These remote work tools have literally saved me from so many potential disasters:
A reliable backup internet (because hotel WiFi can be a LIE!)
Noise-canceling earbuds (so much smaller than big headphones for packing)
Laptop stand that folds flat (posture matters, even on vacation!)
Power bank for those “outside” work sessions
Extension cord with outlets and USB ports
VPN service (some work systems get weird about "foreign" IP addresses)
Tip: Use cloud storage, project management apps, and communication tools to keep your work organized while traveling.
Blending Work Days and Vacation Days: The Hybrid Approach
This is literally the magic formula that makes work and travel actually enjoyable instead of stressful. Here's what worked for us:
For Work Days:
Schedule your must-do work tasks for your peak productivity hours
Block focused work time in 90-minute chunks with short breaks
Use lunch breaks to connect with your family (quick dip in the pool!)
Save administrative/less-focus-intensive tasks for late afternoon when vacation vibes are calling
Set clear boundaries with work about your availability (turn off Slack notifications after your workday!)
For Vacation Days:
Schedule the most important or time-specific activities for your full vacation days
Save activities that can be done anytime (like just enjoying the beach) for post-work hours
Book special dinners or sunset activities for workdays to still make them feel special
Consider paying for convenience on vacation days (like guided tours) to maximize limited time
We made sure to schedule our one big island-hopping tour on our Friday vacation day so we didn't have to worry about getting back for any calls or deadlines.
The Art of Disconnecting When It's Family Time
This might seem obvious, but it's actually the hardest part of travel and remote work with family for most people! When you're done working, be DONE.
Some boundaries that helped us:
Close your laptop and put it away completely (out of sight!)
Have separate work and personal phones if possible
Set "vacation auto-reply" for after your work hours
Change into "vacation clothes" when work is done
Create a little end-of-work ritual (for us, it was jumping in the pool!)
I know this video—I mean article—is getting long, but this part is so important! Don't be that person checking emails while your kid is trying to show you the sandcastle they built. When work time is over, be present with your family.
The Economics of Work and Travel: Why It Actually Makes Sense
So let's talk money for a sec. Choosing to work and travel instead of taking a traditional vacation can actually be more economical in several ways:
You're using fewer vacation days for the same amount of travel time
Having a kitchenette means you're not eating out for every single meal
Staying for a longer period often qualifies you for weekly rental discounts
You can travel during shoulder seasons when prices are lower (since you don't need to schedule around school breaks exclusively)
Mixing work and play means you might be able to take more trips throughout the year
For our Boracay trip, we actually spent less than we would have on a shorter "full vacation" because we cooked most breakfasts and lunches ourselves, got a discount for staying a full week, and traveled during a slightly off-peak time.
Is Travel and Remote Work With Family Right for You?
I'm just going to be honest – this style of travel isn't for everyone. You might want to try it if:
You're comfortable with your remote work setup already
Your job doesn't require constant meeting attendance
Your kids are either very young or old enough to entertain themselves for periods of time
You and your partner are good at tag-teaming childcare
You're okay with a slower pace of travel and "living like a local"
You can mentally separate work time from family time
We've now done three of these work and travel trips, and each one gets easier as we refine our system. My son now knows that "when Mommy's at the desk, it's work time, but when the laptop closes, it's adventure time!"
Final Thoughts on Mastering Work and Travel
The beauty of blending remote work with family travel is that it opens up so many possibilities that traditional vacation time just doesn't allow. It's not about working through your vacation – it's about bringing your work to a place that makes you happy, so the hours you do work feel less draining.
Our week in Boracay gave us precious family memories, beautiful beach time, AND I stayed on top of all my work projects. We came back refreshed instead of stressed about catching up, and we still have most of our vacation days saved for other adventures this year.
Would I recommend trying travel and remote work with family? Absolutely! Start with a shorter trip to test your systems, and then expand as you figure out what works for your family.
So, gear up, plan your next adventure, and remember: you’ve got this. Every day is a chance to blend productivity with passion, and every trip brings you one step closer to the perfect work-life harmony.
Happy travels, and here’s to creating memories, achieving goals, and living life on your own terms.
Thrive Remotely, Live Fully. ✨