For most of the first half of this trip we’ve set out from one destination and headed directly for another. We started in Toronto and knew we’d stop in Niagara Falls, Pittsburgh, Wytheville and Savannah on route to Orlando.  We’ve also known generally where we’d stay. We booked our stays in Wytheville (The Bolling Wilson Hotel), Savannah (Hampton Inn and Suites) and Orlando ( a gorgeous 2-bedroom townhouse at Regal Oaks) either before leaving home or on our way down but each time we knew what we wanted – a boutique hotel, a good free breakfast, room to spread out – and booked that in advance.

Bolling Wilson Hotel

The lobby of the boutique Bolling Wilson Hotel

But since leaving Orlando, our approach has been different. We knew we wanted to get to New Orleans within two days when we left Orlando and we knew we couldn’t do the drive in a single day but that’s about all we knew. Where we’d stop in between was left to be determined by how we felt as we drove (Did we need a break? Did we want to drive on? Were the kids itching to stop?) and what we needed (Sleep? A swim? A great breakfast?).

This approach –  leaving things to chance and seeing how things turn out  – is something that both thrills and terrifies me.

A new-to-me place is easier when I’m traveling alone. With the kids – although they have yet to complain about anything –  I find myself second guessing my instinct. I tend towards city names I recognize for overnights and use a faulty system of historical reference in deciding against others.

On this trip it was the kids who changed that. When I said we needed to stop driving in west Florida they protested. They wanted to drive further and get to Texas sooner. I gave in to the pressure and we pushed on.  It resulted in an experience I’m so glad we had. Our overnight stop turned out to me Mobile, Alabama.

And our hotel pick? The Malaga Inn.

Malaga Inn

Malaga Inn, Mobile, Alabama

The historical property was fantastic and friendly and Vonnie who checked us in was a wealth of local information. It also meant that we were able to explore the USS Alabama the next morning and see the real Calamity Jane. The boys still count it as one of the best experiences.

USS Alabama

USS Alabama

Other lessons I’m learning on this trip:

Lesson #1: Give the kids some control

The first lightbulb moment was when, to give them something to do in the car, I handed them the iPad, told them our budget of $200 for the night, pointed them to the Expedia app and told them they’d be in charge of picking our New Orleans hotel. They jumped at the offer. For the next hour or so they pored over the app, arguing about whether a pool was better than a hot tub, debating the distance from Cafe du Monde as an important factor and asking things like “What’s a continental breakfast?” (and then quickly ruling that out as an option for our food-loving family).


From my seat up front I was pleasantly surprised by their diligence. And when in the end, they presented me with two options, impressed with what they’d picked. In the end we  leaned towards their first choice: The Holiday Inn New Orleans and it was fantastic. The hotel had been recently renovated, the staff was friendly (the boys told me they’d read good reviews online) and the location was perfect. Even better? It was one less thing I had to worry about.

Holiday Inn New Orleans

The rooftop pool at the Holiday Inn New Orleans may have been a selling factor for the kids.


Holiday Inn New Orleans

The 150 ft clarinet that adorns the side of the newly renovate Holiday Inn in New Orleans.

Lesson #2 – Use long drives to book surprise adventures

Ish likes to drive and the boys have a bit of a routine in the back seat. They’ll read, play games, argue, make up and make videos as we go. In the front seat I’m comfortable to be working, chatting and looking out the window. But every so often I’ll hop online and see if there’s something I can do to surprise them. I find activities from reading up on the destinations as we go and/or simply noticing a huge mural from the window for a family photo.  The stops force us to get out of the car, stretch our legs, get some giggles in and reset. On this trip I’m also using the @Expedia app to choose a few activities we can do together. They never know ahead of time. Sometimes the surprises are met with glee ( The Kennedy Space Center)  and sometimes they start out a bit resistant (our cooking class in New Orleans) and then love it more than they imagined.

New Orleans School of Cooking

The skeptic before our New Orleans School of Cooking class


Skeptic no more!

Skeptic no more!

(Yesterday we took a 4X4 Jeep tour of the Grand Canyon that knocked their socks off ! Booking was as easy as

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Lesson #3 – Be open to changing your  route

We are now officially halfway through our road trip  ( 13 states in 15 days!) and while the first half of the trip was fairly well scripted, this second half is a lot more “let’s see where the road takes us.”Just like we did on our trip around the world, we started out on this trip with a general route in mind. We started out following it like gospel but as time has gone on we’ve learned to sway. For example: According to plan we were going to go to Odessa, Texas from San Antonio, instead we found ourselves in Alpine, searching for alien lights and discovering incredible murals.

Alpine murals

We should’ve headed directly to Albuquerque and Santa Fe; instead we opted for Roswell, New Mexico and the UFO museum and an extra night in the Sedona area.  Deciding to change our route has opened us up to new adventures. And isn’t that the whole point of a trip like this?

Aliens Roswell

Alien encounter in Roswell, New Mexico

These are all lessons we’re learning as we go. Sometimes we arrive in a small town and aren’t sure we’ve made the right choice, but by the time we leave with some new memory or shared inside joke, we realize it really isn’t about where we are as much as that we are experiencing it together.  We’re still keeping track of everything through the Expedia app ( I get gentle buzzes on my wrist throught the Apple watch everytime I update the itinerary) and we’re learning that the less planned the destination the more likely that all of us will come away learning something new.

I like to think of it as spontaneity with a safety blanket.

apple watch expedia

Detailed itineraries right on my wrist.

The Great Big Summer RoadTrip is subsidized in part by . Visit  and  follow along on our #ExpediaRoadTrip on Twitter and Facebook . As always, all opinions are my own.