Traveling with Grandparents + Level Up Your Labor Day Fun

Peek inside for kid-friendly travel inspiration, delivered to your inbox every week.

Beepity-beep-beep-beep! Family travel news alert: Multi-generation travel—travel that includes your parents or in-laws and your kids—is the top trend this year. In fact, 55% of families report planning a multi-gen trip within the next year, according to Skift Research’s 2024 State of Travel report.

We totally get it. More hands make travel with kids a bit easier, and it often allows an evening out for mom and dad. That’s why we’re highlighting our best tips for choosing a vacation destination that suits grandparents and kids of ages alike.

And with the Labor Day ahead, you’ll also find suggestions on quick ideas for leveling up the long weekend, whether you’re adding some kid-friendly festivities to your road trip or simply finding a fun activity for Sunday afternoon.

I’d love to hear your feedback. Simply hit “reply” on this email and shoot me a note!

Where to stay with grandparents, too

Here, we’re offering a slimmed-down version of our tips to ensure a win-win vacation with parents or in-laws and kids to boot. Want to find some inspo for your next trip now? Head on over to our listings labeled: Ideal for Multi-Gen Travel.

  • Choose a destination that offers relaxation and fun. How about an outdoorsy cabin that offers nearby hiking trails for you and the kids, some easier trails to accommodate nature walks with the grandparents, and a covered back deck with views for slow mornings sipping coffee? Finding destinations that blend adventure and ease, excitement and peacefulness, and a bit of coziness and curiosity will ensure that you’re appealing to all ages.

  • Consider a vacation home rental. A home-type retreat will offer lots that hotels and resorts simply cannot, including: spacious common areas for everyone to gather comfortably, kitchens to avoid waiting ages for a large-group table at restaurants, and the type of just-us privacy that feels special and memorable.

  • Stagger arrival dates. Sometimes, a vacation feels easier when there’s a day or two to settle in as just a nuclear family before grandparents arrive. This shortens what may feel like too long a trip for grandparents, but still allows everyone to enjoy the fun.

  • Determine how you’ll split the bill in advance. Chat ahead of time about how travel costs will be split between travelers. Whichever approach you choose, be sure that everyone is on the same page when extending an invitation or beginning travel talks.

Level up your long weekend

Looking for ways to make the long weekend feel a little bit more special? We’ve got some easy ways to create memories that’ll last long past Labor Day.

Kick off 1,000 hours outside! It’s easy to live outside in the summertime, but the turn to fall makes getting into nature a little less likely. Use Labor Day as your annual reminder to commit to and track 1,000 hours outside. The 1,000 Hours Outside website offers free downloadable trackers to color in as you go.

Plan a bonfire feast. Build a big one and then make an entire meal right there around the campfire. You can start by cooking corn in its husk, roasting some hot dogs or whipping up pizza pies with our favorite cast-iron cookers, before finishing with your preferred s’more recipe.

Create a backyard challenge. Grab a quick-delivery bubble machine off of Amazon. Set up an obstacle course using stepping stones, beach balls, hula hoops, chalk hopscotch and kiddie pools. Or head over to Facebook Marketplace and nab a new-to-you scooter for a change of speed.

Find a new, nearby trail. No weekend plans? No matter. Throw on your dirtiest sneakers, grab cold waters, pull together a picnic lunch and go on an afternoon adventure. We rely on All Trails for kid-friendly recommendations but encourage you to read reviews and check elevation to ensure you’re choosing an option best suited to your family.

Having kids is a reason to travel, never a reason to stop.
- Unknown