Creating a Basic Itinerary: The First Step in Crafting The Ultimate Road Trip!


If you’ve been following us on Facebook and Twitter then you know we are planning an awesome trip to New York, New Jersey, and Pennsylvania next summer to tick another three states off our list. At the end of next summer we’ll have visited 46. Our trips are not only an annual tradition, but over the last 10 years have become legend. So while it wasn’t surprising, it was still a thrill to hear that Lilia, my college age daughter, when asked if she still wanted to go gave a resounding “YES”. It warmed my heart to know that for her, summer just wouldn’t be the same without “The Road Trip”. So how does it all happen? How do I come up with our route and loose plan from which the rest of the trip will evolve in the coming months? I get asked that question all the time. In this post, I will use my upcoming road trip as an example while I explain and give you step-by-step instructions to plan an awesome road trip of your own.

imgres-1Step 1Decide how long you’ll be traveling-From a sheer exhaustion point of view I know from experience that 12-13 days is our limit. Sometimes we can do it in less time but it all depends on where we’re going and how much ground we want to cover. After 13 days I can’t look at my suitcase, let alone my kids and I am dying for my bed and shower in the comfort of my home. Your capabilities may be more or less than mine, but either way, decide on your limit and go with it. Now you can start figuring out your starting and stopping place(s).

Step 2Decide where you’ll start (an end) from-Try to find a city with an airport that offers reasonable prices and nonstop flights whenever possible. When planning your own trip you may have a couple of different options for airports so choose the best and most economical option and start your trip from there. If you’re driving from home, lucky you! Since I am traveling from Southern California I’ve got to pick a city I can fly in and out of that works for us. This trip is easy to decide since there are lots of convenient flights to Newark or JFK. Having experienced both airports in the past, I will take Newark over JFK any day of the week.  Now that we’ve got our airport covered I guess for us the best place to start is New York City.

gotta try a philly cheese steak

gotta try a philly cheese steak

Step 3-Make a list of the cities you’d like to explore– Using an atlas or Google Maps check out the area you’d like to cover and see what cities and landmarks you can hit.  Think about the places that you definitely want to check out.  On my trip I know I want to see the Pennsylvania Amish country, Pittsburgh, and even Niagara Falls near Buffalo NY. I want to hit all the capitals of the state’s we’re visiting so I have to take that into account too.  Make your wish list and then see what’s realistically doable. For inspiration, I also like to do a word association game with my family to give us some good ideas.  I name the state and they list things they associate with it off the top of their head. For example..Pennsylvania-Liberty Bell, Independence Hall, Cheese steak sandwich, Snyder’s pretzels, Amish, Hershey chocolate … you get the idea.

Step 4-Decide on your route. Using a road atlas or Google Maps take a look at the area you’d like to cover and see which cities you can reasonably get to either using the scale or the directions button on Google Maps. Zoom in and out to see the entire state or a particular leg of your trip. Ideally your overnight stops should be about 2-3 hours max from each other (which should roughly translate into about 150-200 miles). This assures your trip is more about exploring and not about driving. Bigger cities usually have better options for hotels and eats and even night time activities so I always try to schedule my stops that way.  I try to work in a loop moving in a large circle from one city to the next ending in the city I started in.  This makes it infinitely easier when booking flights and returning the rental car. Just to give you an idea, here’s how my trip works out.imgres-3

• Day 1-Fly to New York (Newark)

• Day 2-New York City

• Day 3-New York City, Brooklyn

• Day 4-New York City, Bronx, Queens or Long Island

• Day 5-Atlantic City

• Day 6-Philadelphia


• Day 8-Harrisburg

• Day 9-Pittsburgh

• Day 10-Erie

• Day 11-Buffalo

• Day 12-Syracuse (or somewhere nearby)

• Day 13-New York–fly home

I made a list of everything I wanted to see (and taste) in NYC so it looks like we will need 2-3 days there.  I can’t commit yet until I really delve into the activities and figure out roughly how much time I’ll need, so I’ll leave that loose for now and just assume it’s 3 days. Looking at the rest of the places that are on my must see list for the entire trip, it looks like we can spend a day in each place-and 2 in Philadelphia- with 2-3 hours max on the road per day. Sometimes you’ll find a place you wanted to visit just isn’t possible as it’s just too far or out of the way. Trying alternate routes can sometimes make a difference, other times you might just have come to terms with the fact that you just can’t squeeze it all in. In any event, using these 4 steps should give you a skeleton itinerary that you can then start to fill in with more detail later.  Remember, everything is still loose at this point but at least you have a general idea of where you are going.

And there you have it … the beginnings of your road trip itinerary.


  1. Nicole White says:

    I LOVE the planning phase of road tripping!

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