How to Create a Road Trip Itinerary

It's the fifth week of our Planning a Back Roads Road Trip series, and we're sharing suggestions for planning your itinerary, from selecting your destination(s) to finding the route to take you there.

When planning a vacation, some people like to wing it and leave the entire trip open to surprise.  Others plan down to the minute and know exactly what to expect each day of the trip.  Still others will fall somewhere in between, which is what we'd recommend for most road trips.  You've probably got specific dates that you'll be working with, so you'll want to plan to do and see as much as you can in that time period, while staying on track so you return from your trip on time and having fully enjoyed your time off.


Here are our suggestions of things to consider as you plan your road trip:

When do I go?
Consider the weather in the location(s) you'll be traveling.  If you'll be traveling in the middle of February, it isn't a great time to visit to Glacier National Park for a drive along Going to the Sun Road.  In July or August, it can be HOT and HUMID in the South.  Spring and Fall will generally be a good time to travel most places and you'll avoid extreme or uncomfortable temperatures.  

Find out when the high season is in the area you will be traveling.  Remember that places like Key West have their busy season in the winter months when the rest of the country wants to escape their cold and snowy weather and will therefore be more affordable and less crowded during the warmer months, and places like Mackinac Island, Michigan or Bar Harbor, Maine will be expensive and overcrowded during the summer.

The Grand Hotel on Mackinac Island had just opened up when we visited in mid-May, 
but on the cold, windy day, we had our choice of white rockers on their giant front porch.

A few weeks later, the island would have been much more crowded!

Check local calendars for events.  Also, consider holidays or local events (graduations, parades, festivals, etc.) that may increase the cost or create a shortage of hotel rooms.  We were in San Francisco for Memorial Day weekend so didn't have much trouble finding a reasonably-priced hotel at short notice, but had we been in a beach, lake, or mountain town, it may have been harder to secure one without making a reservation far in advance.  If you're not traveling specifically to attend an event or for a holiday weekend, you can save money by traveling at a less busy time the week before or after a holiday, if you are able.

Where do I go?
One of the joys of a back roads road trip is not knowing exactly what's next and letting the road lead you to your next stop.  That being said, you have to start somewhere, and it's a good idea to have a general plan when you begin.

Determine points of interest.  Think of places you've wanted to go but never have.  Find that box of brochures for interesting looking places and activities you've collected from hotel lobbies over the years (or am I the only one who does that?).  Look at your Pinterest travel boards.  Grab your 'bucket list'.  

Now pull out a road map or print out an outline of the US (or whatever country you will be visiting!).  Mark the locations of the places that you would like to include in your itinerary.  If there are locations you're unwilling to miss on this trip, mark them in red or with a star so you don't forget about them!

When we pulled out of our driveway to begin our adventure, the only plan we had was to roughly follow this route, making sure to visit each state.  We made our reservations for our first stop (Tampa, FL) a few minutes before we left.

We really didn't put a lot of time or effort into planning this route,

mainly drawing it out so our friends and family could visualize our plan.

How do I get there?
Sketch your route.  Now it's time start sketching out a route on your map.  Start from your hometown and pass through all the areas you've marked as MUST DOs.  

Additional attractions:  Now consider which additional attractions you would like to visit if time allows.  Are they close to the rough route you've just drawn?  If so, it's likely you'll be able to add them to your final itinerary.

Something I did a few times during our trip was to check Roadside America for interesting attractions and oddities that would be near our route.  That's how we wound up seeing sights like...

The Grill that cooked the World's Largest Hamburger in Rutland, North Dakota was only two miles off our route.

I love a good jumping picture! 

The World's Largest Ball of Twine in Darwin, MN.  Again, this roadside attraction was just a few blocks from our route. 

The filming location of the movie Field of Dreams in Dyersville, Iowa.  When we pulled up, a man was out tossing a baseball on the field with his grandson.  In talking to them for a few minutes, we found out that the man had been one of the ghost players in the movie.  This one was a little bit out of the way, so we adjusted the route slightly but still wound up where we needed to go!

I kind of wanted to stay and live in the farmhouse, 

which has a great view of the sunset over the nearby cornfields.

I didn't discover this method of discovering nearby attractions/tourist traps until late into our trip and wonder what we else we might have come across had I used it earlier.  Checking it as you plan your itinerary would provide options for interesting places to stretch your legs as you travel!

Finalize it!  Next, you'll need to use a road atlas or Google Maps/iPhone Maps/GPS to plan your actual route.  Of course, we recommend taking back roads because they're more fun.  If you're new to road trips or only have a limited time for your trip, you might need to take at least part of the route on the interstate.  

For a long road trip, it would be overwhelming to do this step all at once.  We chose to look at the atlas every few days to figure out what route to take, then we'd repeat the process a few days later.  

Destination Road Trip.  Is there a large concentration of places you'd like to visit in one part of the country?  Do you want to drive the Pacific Coast Highway or Route 66?  If the area you want to visit is far away from where you live, your best bet may be to fly to that area and rent a car so you can maximize your travel time, instead of taking several days to reach the area you want to explore.  This is the way we explored the Pacific Coast Highway in 2010, and we'd highly recommend it!

One of the highlights of that trip was 
spending a night on the Queen Mary in Long Beach, CA.

Where should I stay?
This really depends on your budget.  A few recommendations:

• Choose one or two hotel chains and earn points toward free nights by staying mainly within these brands.
• Many hotels include free continental breakfasts.  We would highly recommend staying at these hotels most nights!
• Find a quaint bed and breakfast or two; these are a fun way to meet people you wouldn't normally meet at a big hotel.  Plus, their breakfasts are usually cooked to order and very tasty, which is a nice break from restaurant food.  Sometimes these will be a splurge; sometimes, they're comparable to the cost of a chain hotel.
• We've never used airbnb or similar sites because we're more comfortable in hotels, but of course you may be able to find cheaper options that way.

Breakfast at Betsy's B&B in Montpelier, Vermont was delicious and
we enjoyed talking with the proprietors and other guests while we ate.

How long will it take?
It's hard to judge the exact pace of a back roads road trip.  As we've mentioned here before, sometimes our plans for the day change at the last minute as a result of something we come across.  Even when this doesn't happen, sometimes you decide you'd like to spend longer visiting a location than you'd originally planned for.  When this is the case, you just have to make adjustments for the remaining days in the trip to make sure you arrive home on time.  The rough calculation we used was that the back roads took about 1.5x longer than the interstate (this accounts for both slower speed limits and random stops to take a quick picture).  Then for every 3-4 hours, add about 20 minutes for bathroom/gas station stops.

How detailed should my itinerary be?
For your must-do items, make sure you're aware of their hours and the dates they're open.  For instance, some restaurants and museums are closed on Mondays.  Many places, especially family-owned operations, are closed on Sundays.  It's harder to find any kind of restaurant in small towns on Sunday nights, so plan ahead for your Sunday dinner!  Also, if you're driving between time zones, remember to take the time change into account! 

Beyond that, the amount of detail you include on your itinerary is up to you.  

What else?
Make sure not to over-schedule yourself.  It's not very fun to rush from one attraction to the next, worrying all along about having enough time to do it all.  Decide which ones you'll do and accept that the others will have to wait for the next time.

Be willing to cut an item from the itinerary if you decide you'd rather spend longer doing something else.  Add the items that get cut to the 'list of things I want to do one day' or forget about them altogether.

When making reservations in advance, make sure they can be cancelled so you have some flexibility with your time.  On Route 66 in particular, we found that our speed slowed to about half our usual rate because we stopped so many times along the way, and as a result our overnight plans changed a couple of times.

Drive during the day.  You'll miss a lot of pretty sights by driving at night, which we had to do a few times, most notably between Los Angeles and Death Valley.  We knew we were missing some amazing red rocks as we drove into late evening.  More importantly, it's easier to follow unfamiliar roads in daylight!

We saw this colorful sunset outside of Bryce Canyon 

National Park on the way to our hotel in Kanab, Utah.

The point of a back roads road trip is not to get to your destination as fast as possible; the trip itself is the destination.  The idea is to experience the country with your travel buddy(ies).  Remember to allow time to stop and smell the roses.  Get a cup of coffee at a local shop.  Take a walk at a park.  Enjoy the ride!

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