How To Make A Work-cation Trip With Kids Successful

If you still have work-from-home flexibility, now is the time to take advantage of the time and plan a work-cation trip with kids. Being able to successfully manage work and (maybe school too) from the road can lead to making lasting travel memories. Working from home during the pandemic has allowed many people additional flexibility beyond their standard vacation time. Although the travel landscape looks different this year, travelers are longing for a change in scenery and looking to outdoor destinations as the weather warms and the pandemic still lingers.

Our family was featured in a story from the CBS Chicago affiliate station on this topic last fall you can view here. We’ve done many work-cation trips over the last year and we’ll share with you how to successfully plan your own.

6 tips for a successful work-cation trip with kids

1. Plan ahead for your work-cation trip

Booking early is key as demand for long-term lodging options has grown steadily over the last year. The average length of a hotel stay in 2020 was at 5.2 days, up 35% and the trend is predicted to continue for 2021 according to travel data company RateGain. Bookings for vacation rentals in the US are also up by almost 30% YoY according to a recent Home2Go report.

2. Timing is everything

If you plan to road trip, consider driving on the weekends so you’re in your location and set up with wifi during the workweek. Also consider going in the off-season, which for most destinations would be spring and fall to get the best deals. This of course depends on your destination but can help lessen crowds as well as save on cost.

If both parents will be working and childcare is needed, alternating working and time-off with a spouse can be helpful or working part of the time in the evenings. Distance learning from the road may also lend itself to working around class call times and then exploring in the off times. 

3. Pack smart for your work-cation trip with kids

A few good packing tips can go a long way in organizing a longer trip with kids. If you’ll be traveling by car here are a few of the things that have helped us on many of our 4-6 week work-cation trips.

  • Use a car top carrier. This helps create extra space and save room inside the car. Our favorite one is the Yakima Skybox (we went with Carbonite 21) and if you don’t already have a roof rack this one from Rhino Rack is easy to install. There is a fit finder where you put in make/model of your vehicle. We found this easy to install ourselves and we’re not handy. For the Yakima we recommend buying this in person locally vs online as it’s really hard to judge size.
  • For packing, clear plastic bins work better than loose bags and allows you to easily see what’s inside. If there’s something you think might be needed on the way, like jackets or a change of shoes, pack the whole family’s items in one bag or bin and pack this in last.
  • Clothing works best in duffel bags like this especially for fitting in a car top carrier. We like to use packing cubes (get the large size!) to easily separate family members clothing. We give each member or those staying in the same room a designated color and then it’s easier to pull out the cubes and organize once arriving. Plan a one-nighter bag if you’ll be driving for longer than a day to your main destination. This helps have all your family’s clothing and toiletries quickly accessible for the nights before getting to your final destination. We love this Samsonite bag for this purpose and it’s also a great carry-on piece when flying.
  • For road trips, we always pack a cooler. If you’ll have a long trip with multiple destinations, consider the food you’ll want to bring between locations. Buy groceries and bring them between locations as this can be a time and cost saver. For longer trips, we like Blue coolers and find they pack efficiently, keep things cold for up to 5+ days, and have wheels (most good ones don’t). For shorter trips or if you’ll be flying this fold flat cooler is great cooler for day trips.
Child studying from vacation

4. A great place to stay can make or break a work-cation trip

Be realistic about the space and setup you’ll need to be successful working, schooling and staying for a longer period of time. Do your kids need their own space to be happy? Will you need a quiet space for work calls? What will entertain your kids while you are working? Are there any safety concerns for the kids like pools, stairs or unfenced areas if they’ll be playing while you are working? Would you prefer to stay in one location or break-up the time and stay in multiple locations? Thinking through these questions in advance and picking accommodations that will be conducive to work and fun for downtime will set the trip up for success. 

Pro Tips

*Book vacation rentals with built-in entertainment for kids. A game room, fort area, fenced yard, pool, or park nearby are great ways to entertain kids while working. We also love to look for unique stays on farms, castles, container homes, etc. Hotels with pools or other activities for kids onsite are also great options.

*Always confirm the strength of the wifi in advance. Also, check your cell carriers coverage map before you book a vacation rental. If you’re staying in more rural areas or near national parks this is especially important.

*Work setup: many vacation rentals have desks, monitors or printers so look for this when you select a place. If not, don’t be afraid to bring what you need to be successful. Much easier to do if you’re driving! Having the work setup you need will lead to less stress and greater productivity. Many larger hotel chains have great conference room and work setup options.

*Vacation rentals booked for seven days or longer typically offer a 10-15% discount. Month-long rentals will yield the greatest savings if you’re ok staying in one location and doing day trips. If you’re not seeing any discounts reflected it doesn’t hurt to message the owner and ask. Remember being friendly and showing you’ll be a good renter goes a long way!

5. Double your time

If you have scheduling flexibility, consider doubling the time you’d typically spend on a typical vacation without working. This helps to not feel stressed about working and getting in the sightseeing or outdoor exploring you’d like to do.

6. Update calendars before you leave

If you can review work and school calendars before leaving you can ensure any scheduling conflicts with time zone differences can be reshuffled in advance. If you’ll be in a different time zone than at home it helps to add both timezones to your calendar for ease in tracking differences and future scheduling. If your vacation destination will be in an earlier timezone it can help to get work/school calls finished earlier than normal and get in extra sightseeing time.

Lastly, even though a work-cation trip takes more upfront planning and isn’t completely stress-free because of work, it still provides a change of environment and the opportunity to travel and spend time with family. Travel can do wonders to provide a reset and a new perspective, and after living through a pandemic over the last year we all could use a break. Also, check out our 10 Must-do Tips for an Amazing Road Trip with Kids.

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  1. These are some great tips! Work trips are tricky anyway, I can’t imagine how challenging they could be with kids in tow! Thanks for the great guide!

  2. We have done many work-cation trips and this is a fantastic guide! A primary reason our family homeschooled was to be able to travel more, but it often has meant working while traveling. Mixing the two can be tricky, you have gathered some very useful tips. Pinning to share with others, thanks!

  3. I don’t even have kids and found this post to be so helpful as a freelancer! Thanks for sharing!

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