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How To Plan The Perfect Roadtrip

I definitely think I have a problem. The moment I’m on the flight home from our annual roadtrip, I’m already plotting the next destination. This year we had an epic adventure through Chicago and Wisconsin. We chose Wisconsin as we had visited Louisiana in 2015 and wanted a slightly different culture/landscape to mix things we up. We also wanted a cooler climate (Louisiana in July is not for the faint hearted).  So as soon as we returned from Louisiana, we unrolled our map of the USA and ticked off each of the northern states.  Wisconsin stood out as it had a Great Lake and was the home of beer and cheese.  We also knew we could get to Wisconsin by flying direct from Hong Kong to Chicago. At 15 hours flying time this was also the first time I felt mentally prepared for doing such a long flight with my 7 and 4-year-old.


How do I come up with the route?

Itinerary planning is like a jigsaw puzzle.  Especially when you are completely unfamiliar with the territory.  I start by reading guidebooks and checking out the official tourist websites. Then I post a question on the Tripadvisor Forums, which usually garners helpful responses (although be as specific as you can when you ask questions on there, e.g. ages of kids, how many days you have, what you like to see).  

I then make a list of all the places I want to visit and run all the driving distances through google maps. It’s also worth checking in advance if there’s any key events you want to visit. For example, I read that the Wisconsin state fair was on in Milwaukee in mid August so I made sure to be in town over that weekend.  I also made sure we were in the small town of Middleton, Wisconsin for the National Mustard Day Fair!

How do I book our flights?  
We usually end up taking two flights; the international leg from Hong Kong to the USA (usually LAX) and then a domestic hop. This year had a bonus that despite the long flight to Chicago from Hong Kong, we didn’t have to do any onward flying.  I also choose to splurge all our air miles on this trip so we can do it in style.. Cathay Pacific Business class!  To take advantage of miles upgrades, you need to be on the ball and book your tickets far in advance.  Although our flights were still expensive as I had to buy 4 premium economy tickets, I cannot talk more highly of my time in business. It was AMAZING and well worth the miles splurge.
How do I organise the car hire?  
Stay tuned for tips on how to hire car as we had a few money saving tricks up our sleeves this year.
How do I book our accommodation?  
I book everything in advance, where possible with cancellable bookings. For our Wisconsin/Chicago trip we had a lot of variety, the old ‘hotel, motel, holiday inn’.  We tend to be on the move every 2 nights.  If we are staying just one night, I am happy for us all to share one hotel room. For several nights, I am turning more and more towards airbnb rentals.  You can have space, room to cook, outdoor area all for the same price as one large hotel room.  
My favourite airbnb rental this trip was a tranquil, all american dream home on the outskirts of Madison, Wisconsin.  The kids loved playing in the straw fields and we even had our own fire pit. Airbnb hosts are also great sources of local information.
How do you plan what to do each day?  
Ha! Well I have a comprehensive spreadsheet that lists the following:  
Hotel / Driving Distance / Activities / Restaurants  
Some may think I overplan but I relish this part of travel and when you’ve got young kids in tow, it’s hard to be spontaneous. It’s the little things, such as knowing restaurant opening hours or which days museums are free of charge.
When I arrive in each destination, I also speak to locals and pick up pamphlets in hotel foyers (always check out the discount coupons!)
There are endless online resources devoted to every single town on the planet.  There are also lots of useful apps you can turn to on the road, such as Yelp (restaurant recommendations) and Googlemaps (how did we ever navigate without this).  
As a travel blogger, I also approach the local tourist bureaus who provide handy hints on what to see. I tend to mix up our activities from things I’m interested in e.g. Historic Homes, things my husband is interested in e.g. visiting stadiums and eating big american food and then activities for the kids e.g. Childrens Museums and going to the American Girl store (that may have been the highlight of their trip).
What else do I need to know about road tripping in the USA?
I think the USA must be one of the easiest places on earth to travel as a family. Immigration on arrival can be a pain (don’t forget your ESTA) but outside of that, what a wonderful, friendly nation it is!  Perhaps that’s why we keep returning 🙂
For more US Roadtrip ideas:


  • MummyTravels


    I am bookmarking this – we took our first family road trip this summer in California and can definitely see how it would be addictive. We did AirBNB the whole way. Off to check out a few of your other routes for next year.

  • Leah


    These are great tips! I’m glad you love visiting our country and that you find everyone to be friendly. 🙂 We’re just starting to look into more airbnb properties when we travel- if you’re looking for suite-type hotels, we are frequenters of Homewood Suites by Hilton and Residence Inn by Marriott. They always have a separate bedroom and a kitchen and table. The Residence Inn we stayed in a few months ago even had an outdoor sport court!
    I look forward to read your posts on Chicago- I only live 6 hours drive away and have never been there!

    • Nicola

      Chicago is amazing, have fun!

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