One of the hardest parts of planning a road trip isn’t deciding where you want to go.

It’s deciding where you’re going to sleep.

Do you book every hotel before you leave?

Do you leave everything open so you can be spontaneous?

Or do you wait until you’re on the road and see how far you get?

We’ve tried all three.

And after spending three weeks on the road this summer, I’ve decided I don’t really love any of them.

At least not on their own.

Booking every hotel ahead of time gives me security, but it can also make a road trip feel like we’re racing from one reservation to the next.

Waiting until the last minute gives us freedom, but there’s nothing particularly relaxing about sitting in the truck at 2 p.m. trying to find a reasonably priced, dog-friendly hotel with somewhere for the dogs to go outside.

What works best for us is somewhere in the middle.

And that’s probably how we’ll plan our next big road trip.

The Case for Booking Every Hotel in Advance

There is a lot I like about having hotels booked before we leave.

First, I know where we’re sleeping.

That’s a pretty big benefit.

I can research the hotel instead of grabbing whatever happens to have a room available. I can check the location, parking and the things that matter to us before committing to it.

Traveling with two dogs makes this even more important.

“Pet-friendly” doesn’t necessarily mean our-dogs-will-be-comfortable-here friendly.

A hotel can technically allow dogs and still be a terrible choice for us.

I want somewhere that makes getting them outside relatively easy. Grass nearby is a huge plus. After a long day in the truck, the last thing any of us wants is to turn taking the dogs outside into another adventure.

I also like knowing the cost ahead of time.

When every hotel is booked, a huge portion of the road-trip budget is already accounted for.

There are fewer surprises.

And there is something wonderful about pulling into town after a long driving day and already knowing exactly where you’re going.

The Problem With Booking Everything Ahead

The downside is that the reservation starts making decisions for you.

Maybe you’re having a great time somewhere and would love another few hours.

But your hotel is four hours away.

Time to go.

Or maybe you’re tired earlier than expected.

You’d really like to stop driving.

But you’ve already paid for a room another two hours down the road.

Keep going.

That’s the part I don’t love anymore.

One of my favorite things about road trips is that they can change.

You find somewhere you didn’t expect to love.

Weather changes.

A road closes.

You spend longer in a national park than expected.

Or sometimes everyone is simply done for the day.

A completely booked itinerary doesn’t leave much room for any of that.

And after realizing how much more I enjoy traveling when we aren’t trying to see everything, I don’t want our hotel reservations quietly creating another version of the same problem.

So We Tried Booking Hotels on the Road

On our three-week road trip, we experimented.

Instead of having every night completely locked down before we left, we tried booking as we traveled.

At one point, we waited until around 2 p.m. to decide where we were going to stay that night.

In theory, this sounded perfect.

By mid-afternoon, we’d know how the day was going.

We’d know how tired we were.

We’d know approximately where we wanted to stop.

And we’d still have several hours to get there.

In reality?

I didn’t love it.

At 2 p.m., I don’t want to stop enjoying the trip so I can start comparing hotels.

I don’t want to figure out pet policies.

I don’t want to check whether there’s somewhere nearby for the dogs.

I don’t want to wonder whether prices are going up because we’re booking at the last minute.

And I definitely don’t want to discover that the limited options left aren’t places I actually want to stay.

We gained flexibility.

But we traded away some peace of mind to get it.

Then We Tried Booking the Day Before

This seemed like the obvious compromise.

Instead of booking at 2 p.m. the same day, we’d decide the night before.

That was better.

We still had some flexibility because we weren’t committing weeks in advance.

And we weren’t spending the middle of our travel day looking for somewhere to sleep.

But I still didn’t love it.

After spending an entire day exploring or driving, I don’t necessarily want my evening to become tomorrow’s hotel search.

By that point, I want to settle in.

Take care of the dogs.

Get comfortable.

Read.

Sleep.

Planning tomorrow’s hotel became one more task waiting at the end of an already full day.

It worked.

But it didn’t feel like the answer either.

I Think We’ve Found Our Compromise

For our next long road trip, I think we’ll use a combination of all three approaches.

We’ll book the hotels that matter before we leave.

Those are what I think of as our anchor hotels.

If we know we’re spending two nights near a national park, we’ll book it.

If we’re meeting family somewhere, we’ll book it.

If there’s a destination where pet-friendly lodging is limited or prices are likely to climb, we’ll book it.

And obviously, we’ll book our first night.

Those reservations give the trip structure.

But I don’t think we’ll book every single night.

Between the anchor hotels, we’ll leave some flexibility.

Instead of having 21 nights that dictate exactly where we need to be, maybe we’ll have several points throughout the trip that give us a general direction.

Then the days between them can breathe a little.

How Far Ahead Should You Book Road Trip Hotels?

I don’t think there’s one answer that works for everyone.

If knowing exactly where you’re sleeping every night makes you feel relaxed, book your hotels ahead.

There’s nothing wrong with that.

If you love spontaneity and aren’t particularly picky about accommodations, same-day booking might be perfect for you.

But if you’re anything like me—someone who likes having a plan and likes having the freedom to change it—the middle ground might work better.

I’d think about booking ahead when:

• You’re visiting a popular destination during busy season.
• You’re traveling with pets and need specific accommodations.
• You’re staying multiple nights.
• You have an event, reservation or family visit that fixes you to a location.
• Hotel choices are limited.
• It’s the first or last night of the trip.

And consider leaving a night flexible when you have several possible stopping points and genuinely don’t know how far you’ll want to travel that day.

The important part is knowing which kind of uncertainty makes you more uncomfortable.

For me, a little uncertainty about where we’ll stop is fine.

Uncertainty about whether I’ll be able to find a decent dog-friendly hotel once we’re already tired?

Not nearly as fun.

The Cheapest Hotel Isn’t Always the Best Road Trip Hotel

This is another thing our trip reinforced for me.

On a road trip, I care less about fancy amenities than I do about whether the hotel makes our evening easy.

I don’t need luxury.

I need comfortable.

Parking that’s easy to access matters.

Being able to get the dogs outside matters.

A room where we can settle in comfortably matters.

A refrigerator can be useful when we’re carrying food.

And depending on the weather, I really love a motel-style property with an exterior door because getting the dogs in and out is so much easier.

Those things aren’t particularly glamorous.

But after eight hours in the truck, they can feel pretty luxurious.

I’d rather spend my hotel budget on a room that works well for how we actually travel than pay for amenities we’re never going to use.

What We’ll Do Differently Next Time

I don’t regret experimenting with hotel reservations on this trip.

That’s how we figured out what doesn’t work.

Booking everything ahead feels too restrictive.

Booking everything the same day feels too uncertain.

Booking every night the evening before still creates a chore I don’t particularly want on vacation.

So next time, we’re trying the middle.

Book the important nights. Leave room between them.

It gives me enough of a plan to relax without turning every hotel reservation into a deadline we have to chase.

Will it work perfectly?

Probably not.

Travel rarely does.

But that’s also something I’m getting much more comfortable with.

The goal isn’t to create a road trip where nothing changes.

It’s to create one where changing the plan doesn’t ruin the trip.

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Keep Reading

If you’re planning a road trip and trying to find the right balance between structure and flexibility, these might help next:

How to Plan a Road Trip Without Trying to See Everything
The bigger planning philosophy behind leaving enough room to actually enjoy the places you’re visiting.

7 Road Trip Do’s and Don’ts I’d Follow Again After 3 Weeks on the Road
What three weeks of real road-trip experience taught us about what worked and what we’d change.

Road Trip Routine: How We Stayed Comfortable for Three Weeks
Our actual routine for making long days in the truck and frequent hotel changes manageable.

How I Make Any Hotel Room Feel More Comfortable
Once we’ve found somewhere to sleep, these are the small things I do to make the room feel better almost immediately.

I Thought Great Vacations Were Supposed to Be Exhausting
Why I’ve stopped believing that getting the most out of vacation means packing as much as possible into it.

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☕ Comfort Corner

These are a few of the little things that help me travel more comfortably. Nothing complicated—just products I actually use and that have earned their place in my travels.

My Travel Backpack
It keeps the things I actually use during the day together and within reach instead of buried somewhere in our luggage.

My Owala Water Bottle
It comes with me everywhere. Having cold water nearby is one of those tiny comforts I appreciate whether we’re driving all day or exploring somewhere on foot.

My Merrell Shoes
If we decide to walk a little farther or take an unexpected trail, comfortable shoes mean I don’t have to think twice about it.

My Fire Tablet
Not every minute of vacation needs to be sightseeing. Reading at the end of the day—or while everyone else is doing their own thing—is part of vacation for me, too.

Find all of my travel favorites in one place.
You can browse my Travel Comfort & Style Amazon Storefront to see more of the things I actually use when I travel.

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Affiliate Disclosure: Some of the links above are affiliate links. That means if you choose to make a purchase, I may earn a small commission at no extra cost to you. I only recommend products I personally use and genuinely believe make travel more comfortable. If it hasn’t earned a place in my travels, you won’t find it here.

Travel isn’t about having the perfect gear. It’s about finding the little things that help you enjoy the journey a little more. These are mine.