My Go-To Travel Tips: Remote Entrepreneur Edition

Look, I love my home. I love it SO much. I love decorating it, living in it, and going home to it.

But you know what I also love? TRAVEL. While I’m a home decor gal (and a homebody in a lot of ways!), my favorite thing in the world is always going to be packing up a suitcase, heading out with my boys, and seeing something new. Like my recent trip to Europe! We spent time in Scotland, England, Belgium and the Netherlands.

And, as a remote entrepreneur, I’ve found ways to travel multiple times a year while still effectively running my business, keeping to all of my commitments, and enjoying every second of my time away *and* my time at work.

Here’s the truth, though: traveling as a remote entrepreneur is a leeeeettle bit of an art. It takes a lot of practice (and some trial and error), and there are a few more things to consider than you’d think. After all, entrepreneurs don’t get PTO and vacation time.

(Wouldn’t that be nice?!)

However, I’ve spent the last several years making sure that I have the traveling and the working piece down to an art — because I refuse to ever give up one for the other, and I don’t believe you have to. Plus, you know me… I love to share!

My Go-To Travel Tips: Remote Entrepreneur Edition

I’m pretty open about the fact that I schedule a lot of time to relax and unwind in my life. (I’m a mom of boys and a business owner. It’s necessary.)

And, while that idea of regular rest might seem like a farfetched idea to some of you (I promise it’s not!), it also means that my approach to travel is a little different than most. While I never want to be plugged in like crazy on a trip, I don’t mind getting some work done as needed — and in fact, I can often do some of my *best* work in the little pockets of a vacation.

So, here are my tips:

  • Bring your laptop:
    No, really. Even if you don’t think you need it… bring it. Heck, it’s the best thing ever if you don’t need it — but you might! Both Bryan and I run several companies. We just like to have them if we need them and we both tend to work in the early morning and/or evening. Unless it’s an overnight thing, the laptop is with me.


  • Scope out the connections:
    It’s always a good idea to know what the internet sitch is wherever you’re going — and I always try to do this. That way, I know if I’m going to be out of the loop, my employees know in advance.


  • Content, baby!: I love using travel for shooting any kind of content for my blog, site, or socials. It’s so easy (I have free photography in the form of my sons and husband, too), and it’s a nice shakeup from my typical backgrounds and settings. Plus, it’s quick and fun!


  • Be strategic with the finances: I love looking for ways to be smart with my $ on vacation, whether it’s earning miles and stocking up credit card points or taking advantage of perks like SkyMiles for lounge access and free wifi. I’m also super cognizant of expensing anything that may be business-related (AKA, when I don’t fly Delta and can’t access free wifi).


  • Protect your privacy: Public wifi networks can be a little sketchy on a good day — but they can be really sketchy on a bad one. I’m pretty obsessive about using a VPN when I travel to keep sensitive client info private, and would totally recommend you do the same.


  • Decide what you don’t want to do: While a lot of work is okay for me to touch on vacation, I do NOT love vacation meetings — and try at all costs to avoid them. Checking on client work and Asana tasks is one thing, but a meeting is a whole other. I do my very best to block out my cal faaaar in advance to avoid them.

And, there ya have it  — some of my favorite tips and tricks to travel (and work) as a remote entrepreneur! Do you have any that I missed? Leme know… I’m always up for something new to try!

July 3, 2024

leave a comment

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.

Sign up for my newsletter for everything Kerry Loves, from home reno deets and blog posts to business tips and life updates.


come join the party!

Follow me over on Instagram for FB & IG ad advice, biz resources, interior design inspo, and a look inside my (not-usually-picture-perfect) life.