10 Ways to Make Life on the Road Feel More Like Home

May 13

Written By Kelly W

We’ve taken a lot of long road trips over the years, ones long enough that they started to feel less like trips and more like a version of everyday life. There was a 6-week road trip through New Mexico, a 2.5-month stretch through the Rockies, 3.5 months across Colorado and Utah, and a full 5 months in New England.

At first, it’s all new and exciting. You’re moving fast, seeing a lot, and figuring things out as you go. But as you’re on the road for weeks or months at a time, eventually that pace stops working and you start wanting things to feel a little bit more settled and familiar.

We were working full-time while we traveled, which meant we needed to sleep well, stay productive, and keep some kind of routine. The more we traveled, the more we figured out what made it possible to actually feel comfortable in all the various places we landed. These are the mostly small, practical decisions that made each new place feel a little more like home!

This is part of our “Living on the Road” series. You can read the rest here:

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1. Bring Your Own Pillows (Non-Negotiable)

This is the hill we will die on. Bringing our own pillows is non-negotiable, because good sleep matters on the road and nothing affects that more than your pillow.

We bring our own pillows everywhere, whether we’re car camping, staying in Airbnbs, or moving between hotels. We use pillow carriers so they stay clean and easy to pack. (These are our favorite pillows, and we use this pillow carrier.)

There’s something very grounding about laying your head down on your pillow at the end of a long day. You already know it works for you. The support is right and it feels familiar. Bringing our pillows with us means sleep doesn’t have to suffer just because we’re in a new place.

We also bring a sound machine, and it’s a game changer! It helps block out small, annoying noises like fridge hums, traffic, or unfamiliar house sounds. If you’re a light sleeper, this makes a huge difference. (I loved it so much on the road that I started using this sound machine every night at home, too.)

2. Pack a “Bed-in-a-Bag”

Along the same lines, we started bringing our own bedding on the road. Our bed-in-a-bag is exactly what it sounds like: one bag packed with king-size sheets, a weighted blanket we use as a comforter, a sound machine, and an eye mask.

This was especially helpful when we were staying in a lot of Airbnbs. I’m sensitive to my environment and a bit of a germophobe, so no matter how clean a place looked, I liked having our own bedding as an option. It gave us the ability to make the bed feel like ours instantly if we wanted to.

It’s a small thing, but it can completely change how comfortable you feel at the end of the day.

3. Build a Routine Wherever You Are

Finding a favorite trail, restaurant, or coffee shop helps create some semblance of routine while traveling, and it makes you feel like you’re actually living in these places, not just visiting. This became one of the best parts of long-term travel!

We stayed in most places for a few weeks, if not a full month, and we were working while doing so. That meant we had the time to settle in, create routines, and start to feel like we actually lived there. We’d find restaurants we loved, coffee shops we’d go to regularly, and trails we’d run before work. Going to some of the same places helps the town or city start to feel familiar in the best way.

You get a glimpse into what life would actually look like in each of these places. And as someone who’s always thinking about all the different ways we could live and all the different places we could live in, it’s really fun to “try areas on,” so to speak. You’re not just there for a couple of travel days, but instead get to build a short-term version of real life.

4. Plan Rest Days

Picking rest days when you’re on the road for a while is so important.

Traveling full-time is incredible, but it can also be tiring—especially when you’re working full-time while you travel. We were working remotely from all the different places we stayed, and eventually we realized we needed built-in days to rest.

Days where we could catch up on work, sleep in, do laundry, reset, or just not go anywhere. Planning these in advance helped a lot. It reduced one of the many decisions you have to make on the road and gave us permission to slow down when we needed it.

5. Choose Predictable Places to Stay

In our fourth year on the road, we started staying in more hotels. Not because we stopped liking Airbnbs, but because we wanted more predictability.

When everything around you is constantly changing, there’s something really nice about knowing what you’re walking into at the end of the day. We leaned into familiar hotel brands (especially within the Marriott umbrella), where the layout, bedding, and overall experience are consistent. That familiarity goes a long way when you’re moving around a lot.

6. Pack for Real Life, Not Just Travel

We don’t overpack, but we do pack what we actually use in daily life. That means all our toiletries. All our work gear. Everything we’d use in our normal routines.

We’ll trim things like jewelry, extra clothing, and shoes, and focus on multi-purpose items. But everything that makes daily life feel normal—skincare, evening routines, small comforts—comes with us. Things you might skip for a one-night stay because they feel extra suddenly matter a lot more when this is your life for weeks or months.

7. Bring Slippers

This sounds small, but it’s one of those things you notice immediately if you don’t have them. We both wear slippers at home, so we bring them on the road, too. Whether it’s cold floors, unfamiliar spaces, or just wanting something comfortable to throw on at the end of the day, this is a small item that can make any vacation rental or hotel room feel more like home.

8. Pack Backup Towels

We pack fast-drying microfiber towels, usually in our bed-in-a-bag!

At hotels this matters less, but when you’re staying in a lot of different places, it’s nice to have a backup towel you know is clean and dries quickly. They pack down really small, so they’re easy to bring along without taking up much space.

And you never really know when you’ll need one. We’ve used ours for everything from regular showers to a very cold, very spontaneous glacier dip in Alaska (true story!).

9. Start with Groceries

One of the first things we do when we arrive somewhere is go grocery shopping. If we’re staying for more than a few days, we try to book places with a kitchen. Having food on hand makes a huge difference. Breakfast is easy. Snacks are covered. You’re not eating out for every meal.

It saves money, but more than that, it helps you settle in faster. Cooking even one meal makes a place feel more like home.

10. Go to Chains (It’s Okay)

Look, of course we want to try new places when we travel. That’s a big part of why we’re on the road in the first place… to experience new places, new restaurants, new activities, all of it.

But when you’re on the road for a while and everything is new all the time, sometimes you just want something familiar. It’s similar to the reason we started staying in more hotels during our fourth Travel Season. We realized that having a few consistent, predictable things in the middle of all the change made a big difference.

When we wanted something easy, something we already knew we’d like, or just a small piece of home, we’d give ourselves permission to go to a chain. When it made sense, we’d prioritize local or regional chains, like Dunkin’ in the Northeast, Tim Hortons and A&W in Canada, or Whataburger in Texas.

The longer we traveled, the more we realized that comfort isn’t about staying in one place. It’s about bringing the right pieces of home with you. When you sleep well, have a routine, feel settled, and can create some predictability or familiarity, everything else about the trip gets better. It helps you fully enjoy the life you’re living on the road—it’s an incredibly special experience!