Route 66 – with a teenager! (2)


Vacations with kids can be demanding.   Vacations with one kid will present different challenges.   Vacations with one teenager.….. well….

There I was – all set to divulge our family secrets and then thought….  Hold on!!   This is the guy I’m depending upon to take care of me in my (rapidly advancing) old age!!!

An abrupt change of tactics required!!   Better make this post less about our road trip and more about Route 66!   That should work! (but not as much fun – sorry!)




This is not a detailed route 66 itinerary.   Its not even a detailed planner for teenagers (you can google some of the 12 million sites for ‘Route 66 with teenagers’!).   This is a general reflection on what worked for us (summer, 2007).



Ok – it can be done in a ‘whirlwind’ if that’s what you want.   If you live in the US then you could do it in stages.   If traveling from abroad you have to allow a few weeks.  You will need a couple of days at either end for Chicago and Los Angeles if you haven’t visited before.  Then there are the ‘add ons’ – Grand Canyon,  Joshua Tree,  Las Vegas…

End to end we allowed 3 weeks and covered 3400 miles.   Our longest drive was 340 miles (St. Louis to Joplin).  There was only one day in which we didn’t move the car (Santa Fe).



Research is very important if doing the trip with teens – is the Springfield Drive-in Movie Theatre open every night?    Where will you find a weekend rodeo?   What attractions are closed on Mondays?   Are you going to try and catch a professional game somewhere?   Whats the cheapest night for accommodation in Chicago / Las Vegas / Santa Monica….

DSCF2415Rodeo,  Santa Rosa,  New mexico


Keeping the Peace

Lets face it – no matter how well you play at happy families,  a few weeks in a car will do everyone’s head in!   There has to be a few rules to help with survival:

*Make sure everyone knows the plan for the day (unless there’s a surprise arranged).  No point in trying to hide that 8 hour drive with minimum stops…

*Make sure there’s a ready supply of (healthy!) snacks and cold drinks on board at all times.

*Even if they have earphones on all day,  you can’t have your own choice of music / radio blaring the whole time.   Encourage your teens to download their own music onto a road trip playlist.

*Physical space – try not to clutter the back seat with extra luggage etc – leave them space to stretch,  lie down,  spread out their stuff.

*Rotate the passenger seat – let the teen sit up front for some part of every day.

*Stop taking offence,  and keep your mouth shut,  if they’re tuned out and not loving the miles and miles of empty highway as much as you do!

*Get out of their way!!!  Give them personal time every day – either stick them under a shady tree or leave them in their bedroom and head off for a walk or a drink…



Are we there yet….are we there yet….. are we there yet…..


*Road signs – put them in charge of spotting lesser attractions and landmarks



*State lines



*Trains and trucks


*Deserted buildings along the route


*Familiar names from TV




This won’t be a cheap vacation.   You’ve most flexibility with accommodation – popular Route 66 motels are obviously going to be more expensive ( and won’t have better facilities) than the regular chains.   Your other major outlays are obviously flights,  car rental,  fuel and food.   RV’s are expensive to rent but might work out better in the long run,  especially if you’ll need more than one bedroom.

You will have to allow for the cost of attractions-  Sear’s Tower,  St. Louis Arch,  Meteor Crater,  movies, etc. – they all add up,  especially with a family.

Blow outs  – try and budget for a major highlight (but not too early in the trip) – there’s Disneyland in Anaheim or maybe a show in Vegas.   We opted for a helicopter ride at the Grand Canyon.



Fine if you’re happy to take your chances but if you’re looking for iconic motels you have to book in advance.  Will you be traveling in the US high season?   Do you want to overnight at the Grand Canyon?   Will you want swimming facilities in the evenings after a long drive?   Does your city hotel have free parking facilities?

I started planning several months in advance so managed to get almost everything I wanted (just not our 1st – or 2nd  – choice at Grand Canyon).   I won’t list all our accommodation here but just a few main points:

*Cities – Chicago,  Oklahoma,  Santa Monica,  Flagstaff,  St. Louis,  etc. –  we just went for convenience and value.

*Santa Fe,  Albuquerque,  Springfield – small motels,  mostly within walking distance of attractions (which means a break from driving).   Bear in mind that Santa Fe is considered one of the most expensive places on the route outside of Chicago and LA.

*Grand Canyon – book this as soon as you’ve worked out your route.  The lodges fill up pretty quickly.   Alternatively,  you can commute from Flagstaff.

*Las Vegas – Do you want weekend or midweek.   Is there a major conference in town that will drive up prices?   You might get a big name casino hotel cheaper than you’d think (but remember the resort fees).

*‘Iconic’ Motels (all should be booked in advance):

Blue Swallow Motel,  Tucumcari,  New Mexico



Wigwam Motel,  Holbrook,  Arizona



Caboose at the Canyon Hotel,  Williams,  Arizona



Big Texan Motel,  Amarillo,  Texas



If booking either a wigwam or a caboose,  its worth keeping it as a surprise if you can….


Food and Drink

With all that driving,  food stops will become very significant events.   If you’re traveling with kids / teens you’re probably looking mostly at diners,  pizza,  fast food,  etc….

*Make a list of those famous Route 66 diners and work them into your schedule for lunch time stops…


*Chicago –  Bring the family for a deep-dish pizza (not really my thing).  There are dozens of pizza joints vying for the top spot so either book a place in advance or just opt for somewhere close to your hotel.

*St. Louis – Its worth joining the queue at Ted Drewes Frozen Custard.  Ted Senior opened his first store in 1929 so they’ve had a long time to perfect those recipes!


*St. Louis – join a tour at the Budweiser Brewery

*Amarillo – At the Big Texan Steak Ranch you can enjoy your own meal while watching someone tackle a 72oz steak! (its free if you can eat it within an hour!).


*Las Vegas – Kids and teens will not be welcome around the gaming areas but they can still enjoy the buffets.

*Oatman  – have lunch in the Dollar Bill Bar and enjoy the decor!



Highlights and Activities


There’s a LOT of driving.   If travelling with youngsters or teens,  you need to try and find something of interest every day.




Sears Tower

River Architecture Tour (you can enjoy the commentary and they can enjoy the boat trip!!)

Go see grant Wood’s American Gothic at the Art institute


Visit ‘the Bean’ at Millennium Park

Get your photo of Route 66’s starting point



Wilmington  Gemini Giant




Lincoln’s Home National Historic Site

Drive-in Movie Theatre





St Louis  Gateway Arch




Marsh Rainbow Arch Bridge




Molly’s Landing – Blue Whale



Oklahoma City

National Memorial



National Cowboy and Western Heritage Museum



Clinton – Route 66 Museum




Amarillo  Cadillac Ranch




Santa Rosa  Route 66 Auto Museum




Old Town

Sandia tramway



Acoma Pueblo Tour




Painted Desert


Petrified Forest National Park

Winslow  Slow down to see THE CORNER made famous by the Eagles hit song ‘Take it Easy’

DSCF2538 (1)


Meteor Crater   Guided Tour



Grand Canyon



Oatman  Gun fights and donkeys on the streets




Las Vegas  Retail Therapy  –  bring them to an outlet mall for their sports gear and new sneakers etc.



Joshua Tree National Park



Elmer’s Place   Bottle Tree Ranch



Los Angeles

Disneyland,   Universal,  etc.

Hollywood Walk of Fame


Santa Monica

Santa Monica and Venice beaches


Don’t forget your route end photo!







13 years later!

One to one 30 second interview (at enormous expense!) with said teenager:

Off the top of your head,  without thinking – what were your favourite bits?

Big Texan Steak House

Chicago – all of it   (that’s a surprise!)

Grand Canyon

Drive-in Movie in Springfield

Vegas even though I wasn’t allowed to do or watch anything

Sleeping in the Train and in the Wigwam


And worst bits?

Santa Fe – all of it – but can’t remember why!

Mexican food – but I like it now!



Small Stuff


Don’t forget:  ESTA    /    Drivers licence   /   Excess car insurance

Would it be cheaper to get a return flight to Chicago and an extra Los Angeles – Chicago flight rather that into Chicago and home from Los Angeles – no harm in checking before you purchase tickets.

Which car rental companies don’t charge excess for a different drop off point (presuming you’re not driving back to Chicago!)

Some diners in smaller towns close up surprisingly early  – don’t dawdle too long at the motel swimming pool without checking restaurant times,  especially mid week.    Bring games etc. for night time entertainment.

Watch out for time zones.  We got a bit cross with a guide at the Meteor Crater because she wouldn’t let us on our prebooked 10.00am tour –  transpired it was only 9.00am!!!!

After flying along for days,   it took absolutely hours to do the last stretch in California due to traffic.   Allow plenty of time if you are heading straight to the airport the same day….




14 thoughts on “Route 66 – with a teenager! (2)

  1. What a great trip and so well organised. Well done also for including you teenager, very difficult, I would have brought a friend along!

    1. Ah we were used to traveling together in those days. We never brought a pal on those summer trips because we’d be away for 3-5 weeks. We were good at managing our own space I think and finding stuff that suited everyone.

  2. Marie thanks that was really interesting and useful if we ever do it. I think 2 teens is worse than one! Less space, constant arguing!, not agreeing on anything. Yes definitely better off with only one!

    1. Sounds like torture Sinead!! You’d love the trip – but all that time with the 2 lads in the back….. Good luck with that one!!!

  3. I enjoyed this post very much, especially the photos of the motels and restaurants along the way. At 2,500 miles (roughly 4,000 kilometers), this trip is not for the faint of heart! I don’t think I know any Americans that have actually done the whole thing, although I’m sure there are a few. Thanks for putting together this interesting summary!

    1. Thanks Carol – it was a great trip. There are sections along the way with very little of interest so there can be long stretches of time with no distractions. That was the toughest part. But there are so many experiences en route that its like several vacations rolled into one. I’m glad though that we did it as one trip rather than breaking it up.

      1. I was going to mention that much of the landscape is just not very interesting, but I couldn’t think of a diplomatic way to say it. (I grew up in Kansas, so I feel that I can be honest about the flat lands!).

      2. Thinking back, there were only a few days which were heavy going. Most of the time, there would be something every few hours to distract. But its one BIG country!!

  4. Hello.

    Wow! I envy you! 🙂 Driving Route 66, has been my dream, but it never will come true. You have made a great road trip report and I do love it. Congratulations!

    Happy and safe travels!

  5. Wow, you guys had a chance to drive the whole length of the Route 66 back in 2007 when the whole world and the travel industry was a completely different place? I bet you made many unforgettable memories! Thanks for taking me along and fueling my wanderlust. Aiva 😊

  6. What a great post. Essential reading if intending to do such a trip. I have what is probably a common ageing male fantasy of revving up the Harley a la Easy Rider, putting on the sunnies and heading steadily west along 66. Maybe meeting my doom in a fireball.

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