How We Handle Mail and Deliveries on the Road

life on the road

Aug 3

Written By Kelly W

When we first started traveling for weeks and months at a time, this was one of the most intimidating parts. How do we get packages? What address do we use? What about prescription deliveries? Mail? Returns? Important notices?

At the time, we were seeing our friends travel full-time in an RV, on a mission to visit every golf course in the United States. I could not wrap my head around the practicality of extended travel and genuinely wondered how they handled these kinds of things.

Once we started living on the road ourselves a few years later, I realized a big part of it is simply figuring it out as you go. You learn how to time deliveries around checkout dates. You get creative with shipping addresses. You learn what needs to travel with you and what you can pick up on the road. Eventually, the things that once felt complicated start feeling normal.

This post is part of our Living on the Road series, where we share what it actually looks like to work remotely while traveling for weeks and months at a time. Keep reading:

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👋 Meet Us: We’re Jonathan and Kelly, and for five years, we lived on the road for weeks and months at a time—working full-time, building routines in new places, and turning everyday life into a series of road trips. We’ve spent our “Travel Seasons” exploring everywhere from the Canadian Rockies and Alaska’s highways to New England in the fall, and along the way, we’ve learned how to make life on the road feel normal, sustainable, and really, really fun.

1. If it can be handled before or after the trip, it is.

This is probably the biggest practical tip we have. Before a Travel Season starts, we try to handle as much “life stuff” as possible.

We schedule appointments for before or after the trip, set up autopay on as many accounts as possible, switch to paperless billing or request emailed statements, and refill prescriptions by requesting larger amounts with less frequent refills.

If we can’t get to it before we leave, we push it until after we get back (if it’s something we can delay).

Part of what makes a Travel Season so much fun is that your focus shifts toward exploring somewhere new, rather than managing day-to-day responsibilities. If something can be handled before the trip, or removed from our plate entirely and handled afterward, we try to do that.

2. Bring it with you.

For things you know you’ll need during the trip, bring them with you whenever possible.

This applies to things like detergent, toiletries, skincare, and makeup, but also checks, cards, medications, and paperwork. Planning ahead helps us avoid extra to-dos on the road and limit the number of deliveries or shopping trips we’ll need to coordinate.

Because we travel by car and stay in Airbnbs and hotels rather than living in the car itself, we can be more generous with what we pack. At the beginning of a Travel Season, we’ll usually bring enough toiletries and everyday products to get us through most or all of the trip. Things like full-size toothpaste, face wash, face and body lotion, extra toothbrushes, and full-size makeup products.

If it’s something easy to replace at CVS, Walgreens, or Walmart, it’s less important to bring it with us (since these stores are widely available across states). But if it’s from Sephora, an online-only company, or a specialty store, I would rather have it with me in advance than spend part of the trip tracking it down.

The same goes with admin tasks on the road. If there’s a check we’ll have to mail or a birthday card we’ll want to send, it’s easier to plan in advance than scramble on the road.

Read next: How We Handle Groceries, Laundry, and Everyday Life on the Road

2. Go digital.

The more digital your life becomes, the easier long-term travel becomes.

Bills.
Bank statements.
Communication.
Account alerts.
Documents.

If something can come through email instead of physical mail, we want it to.

We also signed up for USPS Informed Delivery, which lets us see preview images of what’s arriving at home. That’s been incredibly helpful because even when we’re gone for months, we still know what’s showing up at our home address and whether anything important needs attention.

3. Time deliveries with longer stays

Packages are the part I used to wonder about most, and yes, we still order things on the road all the time. Sometimes we’re replacing hiking gear. Sometimes it’s work supplies. Sometimes it’s random things we forgot.

For me personally, medication deliveries are the most important logistical piece we manage while traveling. I have specialty medication delivered monthly, so before every Travel Season, I’m thinking ahead about where we’ll be staying, how long we’ll be there, whether deliveries are reliable, whether the host allows packages, and how much buffer time we’ll have if shipping gets delayed.

If we’re staying somewhere for a month, that’s the ideal time for a delivery because it gives us flexibility in case there’s a delay or issue in transit. I would not schedule an important delivery for the end of a stay and hope it arrives on time. That’s how you end up stressed out, trying to track a package while checking out of an Airbnb.

Instead, we usually try to schedule important deliveries toward the middle of a stay, ideally during the work week, so we have flexibility on both sides if something goes wrong. We’ve had packages sent to the wrong Airbnb, deliveries delayed until after checkout, hosts receive packages at their own house for us, and packages rerouted to post offices.

When that happens, you figure it out, but it's easier to do so when you’re not also stressed about checking out and moving to a new location.

4. Consider the best delivery address.

At this point, we’ve basically used every delivery option possible. Vacation rentals are usually our favorite because the package comes directly to where we’re staying. However, we make sure to confirm deliveries with a host ahead of time, because sometimes mail in areas is unreliable or will reroute to the post office without warning. And some places don’t allow deliveries for guests.

Hotels can also work well because they’re used to receiving guest packages, though I personally prefer vacation rentals for deliveries because it comes straight to us.

When we can’t reliably receive packages at the place we’re staying, we use post offices. Before sending something to a post office, we confirm:

that the local post office can receive deliveries like this
exactly how to address the delivery
pick up hours and the pick up process
how long shipping realistically takes in the area
that we have enough of a buffer in case of delays

5. Trust you’ll figure it out.

At the beginning, all of this felt like something we had to constantly think about. Now, we start automatically thinking:

Should I order this now or wait until the next stop?
Will we still be here if this gets delayed?
Does this Airbnb allow packages?
Should this go to a post office instead?
Can this just wait until we get home?

These systems become second nature on the road, and there’s something really cool about that. Yes, it can seem ridiculous in the moment when you’re trying to get something delivered to a remote mountain town or timing Amazon orders around checkout dates, but it’s part of what makes this lifestyle so unique.

You’re not vacationing; you’re building a life on the road!