10 Smart Tips for Planning a Multi-City Road Trip

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Multi-city road trips can be a lot of fun. They are great ways to maximize your vacation time. But, they can be very overwhelming to plan. To help you plan your next multi-city road trip, here are some of my best tips!

Over the years, my husband and I have taken many multi-city road trips. In fact, as I’m writing this article, I’m in the process of planning our next one.

I’ve learned a lot about planning them through the process. Each trip we take is better than the one before, thanks to all the lessons I’ve learned. And today, I’m sharing them with you so you can plan your own without getting overwhelmed by it all.

Tip #1: Decide on your starting and ending points.

The first step in planning a multi-city road trip is to determine where you will start and end your trip. Now, most of the time, your starting point will be your hometown.

But, you may decide to fly to another city and start from there. This is a wise choice if you are wanting to road trip in an area that is a long way from your home. Flying into a city that is close to where you want to explore will give you more time to devote to the actual road trip.

When choosing your ending point, think about your various options. You could plan your trip to be a loop, pick a final location and then drive straight back home the last day without any stops, or fly out of a different city than you began in.

Tip #2: Pick a driving strategy.

My next tip for planning your multi-city road trip is to figure out your driving strategy. Do you want to spend one day driving all day and then have fun and explore the next day? Or would you prefer to do a little of both each day? Or maybe you want to do a mix of the two strategies.

By deciding which theory of driving you will follow at the beginning of your planning, planning out your stops and creating your itinerary will be much easier for you.

Tip #3: Determine your stops along the way.

Once you know where you will begin and end your trip and your driving strategy, then pick out what other locations you will visit along the way. If you don’t already have stops in mind, research places that lie along your route and choose places that peak your family’s interests.

Alternatively, you could include some locations that are not directly in your path but that are close by and that your family would enjoy seeing.

Your driving strategy and length of trip will determine how many stops you can make and how long you can spend sightseeing at each destination.

I recommend determining all of your stops before you settle on an exact route. This will give you the freedom to pick places to visit that are not in a direct line between your start and end points.

Tip #4: Figure out your driving route and time between the stops.

Once you know each of your stops, take a look at a map and figure out your exact driving route during each leg. Check how long it will take you to get from one location to the next.

These drive times will partially determine how long you have to spend in each place. I like using Google for this.

You may find after checking drive times that you have to cut out a destination or two. Alternatively, if the times are shorter than you think, you may be able to spend more time in a few of your stops. You may even be able to add in a bonus stop.

Tip #5: Don’t worry about it being equal.

I’m sure you already know this, but in case you don’t: remember that you don’t have to spend an equal amount of time in each location.

Spend as much time at each stop as you need to see everything your family wants to see. For some places, half a day may be sufficient. For others, you may need several days.

Of course, due to the length of your trip, you may have to cut some stays shorter than you would like. But, this just gives you a good reason to come back later!

The benefit of spending longer in one or more destination is that it will give your family a break from the car and allow you to settle into one hotel for a little bit.

And deciding how much time you will spend in each location will make picking out activities to do easier.

Tip #6: Pick out activities.

My next tip for planning your multi-city road trip is to pick out your activities for each destination. Now, you probably already have one or more things in mind, which is what caused you to pick these locations.

Take your stops one at a time and lock in your must-do experiences. Then, look at how much time you devoted to each place. Research other things to do in that location to fill in the rest of your time.

Because you have already figured out your drive times, you should be able to estimate what time you will arrive in each place and what time you will have to leave to head to the next place. This will help you plan your activities out and maximize your time at each location.

This is a great time to reevaluate your plan too. As you research things to do, you may discover that you want to spend more or less time in a particular location. If so, adjust your plan now before locking in your itinerary.

Tip #7: Find your hotels.

Once you have your route and activities planned, then focus on booking your accommodations at each stop.

Whether you prefer hotels or vacation homes, look for places that are close to your chosen activities. This will save you time driving during your stops. And it will maximize the time you have to spend on sightseeing and experiences.

Bonus tip: If you have a long drive between two points on your multi-city road trip (and you don’t want to devote a whole day to driving), consider spending the night halfway between the two points. You can drive the first half of that leg in the evening and then do the second half of it the next morning.

Tip #8: Check the weather.

One of the most important tips for your multi-city road trips is to check the weather for each leg of your trip before you leave home.

This will help you pack for each destination. It will also prepare you for any inclement weather you might encounter along your route. And if you discover that the weather will be really bad in a particular spot, this will allow you to change your route before you head out.

Tip #9: Research restaurants.

Don’t forget to research restaurants at each of your destinations. This is a key piece of planning any trip.

Taking the time to research places to eat will allow you to find the best restaurants for your family and your budget.

I recommend after checking out the menus of restaurants that peak your interests, making a list of those you would like to try on your trip. Include hours and the address of each restaurant on your list.

Then, during your trip, when your family gets hungry, you can pull out your list and quickly find a place to eat.

Tip #10: Pack wisely.

Last up on my list of tips for multi-city road trips is to pack wisely. This can be difficult when moving to a new hotel every few days. Honestly, I still struggle with this one myself.

When packing, think through your trip. The best way to pack wisely is to pack for each segment of your trip instead of packing each family member’s things in a separate suitcase. Personally, I find this hard to do, so if you can’t wrap your head around this, it’s ok.

What I do, instead, is pack for the whole trip in a couple suitcases. Then, once we get past the halfway point of our trip, I condense our clean clothes down into one suitcase and use the other one to hold our dirty clothes.

If you will need special clothes or equipment for only one leg of your trip, pack these things in one small suitcase. Then, you can leave it in the car during the other portions of your trip.

I also recommend packing a few smaller laundry bags instead of one large one. This will make it easier to lug your dirty clothes into and out of hotels at each location.

Bonus Tip: Use a travel planner.

Ok, full disclosure here: this tip should have been included as one of the main tips. But, I forgot about it! So, I went back and included it as a bonus tip. However, that doesn’t mean it is a throw-away. This is one of the most important tips for making the whole trip planning process less stressful!

Multi-city road trips are more overwhelming to plan than trips revolving around one location because there are so many more details to keep track of. The best way I’ve found to solve this problem is by using a travel planner.

I’m not talking about a travel agent. I’m talking about a journal type planner. Having one notebook to put all your details, plans, and confirmations in will keep you organized and help you remember everything you need once you are on vacation.

I first used a travel planner back in 2018 for our trip to New Zealand. It helped me keep track of our plans while planning, During each leg of our trip, I was able to quickly find the information I needed when I needed it. Now, I use them for almost all of our multi-city road trips.

Your planner can be a simple spiral notebook or three-ring binder (this is what I like to use) or a fancy travel planner you buy. Once you’ve solidified your plans, add them to your planner.

I like to start with a general details page that includes any flight and rental car information and the dates of the trip, as well as a list of stops. After that, I include a overall trip itinerary page followed by individual pages for each day’s itinerary. I then include one or more page for each stop that has our hotel information, specific information for planned activities, a list of restaurants we want to try, and any other details we may need for that stop.

Be sure to include a pocket page of some sort to hold any tickets, receipts, or other things you need to hold onto during your trip.

Conclusion

Multi-city road trips are a lot of fun, but they can be overwhelming to plan. These tips should help make the whole process easier for you. Enjoy your next road trip!

For more trip planning tips, see my packing tips for multi-city road trips, how to plan an epic vacation, ultimate guide to travel with kids, and how to take amazing vacations on any budget.

For more road trip tips, see my complete guide to family road trips, how to pack for road trips like a pro, the best road trip snacks for kids, and the best tips for successful road trips with kids.

Happy travels!

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