Road Trip Extraodinaire: 22 states in 17 days

I’m going to apologize up front. This post is super long and that’s why it has taken me an eternity to get it up. I’ve tried to really give you a sense of all that can happen in such a short time when embarked on a well planned road trip. The map gives you a quick look at where we went, so you don’t have to scroll through the entire post if you’re not interested. If you find a location that interests you, scroll down to see if there is anything we found or learned that can help in your own planning.road trip extaordinaire

In August 2011, our family embarked on a 19 day road trip. We travelled across 22 states in our old 1999 Dodge Caravan.  Our round trip took us across prairies, through rolling hills, and vast greenery to the Eastern shores of the Atlantic Ocean.  We passed through the Appalachians, the swamps of Louisiana, the dry Texas plains and the beautiful Ozark mountains.  After 9600 km and almost 100 hours on the road, we arrived home with memories that we’ll cherish for a life time. Of all the vacations we’ve taken as a family, this is the one that stands out for all of us. The endless hours we spent together in the van talking, laughing and listening to music were truly special. Of course, we did many cool things while away, but our time on the road was just as valuable and memorable as the excursions.

We stayed in 9 different locations along our route and spent extra time exploring many of the cities and towns, we stopped in. Below is a list of the places we stayed along our route.

  • Whitehall, Wisconsin
  • Worthington, Ohio
  • Beckley, West Virginia
  • Savannah, Georgia
  • Kissimmee, Florida
  • Monticello, Florida
  • New Orleans, Louisiana
  • San Antonio, Texas
  • Eureka Springs, Arkansas
  • Sioux Falls, South Dakota

Day 1:

We left Winnipeg, Manitoba early on the first morning and drove to Albertville Outlet mall. We stopped and spent a few hours shopping before continuing on to our first destination. We arrived at the Oak Park Inn Bed & Breakfast in Whitehall, Wisconsin.  Linda was an awesome host and the inn was very quaint with beautiful gardens surrounding it. The inn is certainly not posh, but it’s super quaint, clean, family friendly and very affordable. We enjoyed our stay and the hosts so much that we stayed with them again in 2013. Oak Park Inn

Day 2:

We left Wisconsin and enjoyed a beautiful drive through the hills and forests of Wisconsin. I especially loved seeing all of the beautiful old barns that were speckled through the country side. The architecture of many of them was quite different from what you would see in Manitoba. We continued our journey to Worthington, Ohio. This was one of the few places where we stayed in what you would consider your “run of the mill” hotel room for the night. After a long day of driving, we crashed for the night at a Holiday Inn.

Day 3:

The next morning, we got up and ate a good breakfast before making the short trek to Columbus, Ohio where we spent all day on at the Columbus Zoo. This zoo was made famous by former zoo director, Jack Hanna. It was an incredible zoo and an experience that will never be forgotten. Believe me, it was like no other trip to the zoo.

It was a very hot day, but despite the heat, the animals were really active and entertaining. Tim had a “stare down” with a gorilla that had major attitude and it “flipped him the bird” not once, but twice! The polar bears put on quite a show during a mid afternoon down pour and engaged in an impromptu diving contest. It was so amazing and fun to watch. The red masked mandrills were quite entertaining as well. Let’s just say they provided a live display depicting exactly how babies are made!! The Columbus Zoo certainly did not disappoint … it was quite an adventure and a day full of laughter.

We ended the day by clocking up another few hundred km. Adding a few hours of driving at the end of a long day may seem a bit crazy, but it gave us a chance to reminisce about the day and relax after spending hours on our feet in the hot sun. It also alleviated a few hours of drive time from the following day’s journey.  This was one of the few nights we didn’t pre-book as we weren’t sure how far we’d make it after a long day at the zoo. We ended up finding a hotel room in Beckley, West Virginia.

Day 4:

We continued our drive through the gorgeous mountains and lush greenery of West Virginia, Virginia, North Carolina and South Carolina.  We were intrigued by the many signs along the road for  Lewisburg, WV and decided to make a pit stop and check out the town. Although we didn’t spend much time there, we drove down the main drag and a few of the residential streets. The town exudes character and was voted on of the coolest small towns in America. If we ever travel this route again, we would be sure to make the quaint town of Lewisburg one of our destination stops.

We ended day 4 in Savannah, Georgia. We had pre-booked The Marshall House,  an incredible hotel located in the historic district of Savannah. It was built in 1851 and most of the original structure has been preserved.  We were awe-struck by the hardwood floors, original doors, mouldings, staircases, etc.  It was our favourite hotel of the trip!!

That evening, we went out for dinner and enjoyed a beautiful dinner on the waterfront. It was my first time eating Fried Green Tomatoes….mmmm good!  On our way back to the hotel, we came upon a street party celebrating the 92nd birthday of Leopold’s Ice Cream. Of course, we couldn’t participate in the festivities without actually trying some of their famous ice cream. Delicious.

Days 5 and 6:

We spent the next two days exploring the city. Savannah was established in 1733 and its history is reflected in the incredible architecture.  The layout of the city is also very unique, as there are “town squares” every few blocks. The squares  were once business hubs, but now mostly serve as parks.  The kids had a blast running through the fountains in Ellis Square. It was really hot, so the cold water was very refreshing! We also took a guided tour of the historic district in a horse-drawn carriage. It was really interesting to learn about the history of Savannah and some of the homes that are around 200 years old. Crazy!! It is a beautiful city and was a definite highlight of our vacation.

A short drive from Savannah is Tybee Island. We set off early so that we could spend a few hours at the beach before taking off for our next adventure. The kids loved playing in the waves from the Atlantic Ocean, but unfortunately Eden’s retainer was swept away in all the fun!

We left Tybee Island and drove about 4 hours to Cape Canaveral, just in time to board the Orlando Princess for four hours of deep-sea fishing.  We had signed up for the Florida Groupon and were able to pre-buy the tickets at a great price. The ocean was very calm when we left, but a few hours in, we got caught in a squall.  The waves were huge and at times the boat seemed to stand almost vertically before crashing down the other side of a wave. It was a super rocky boat ride, but somehow we all dodged sea sickness and it only seemed to enhanced our adventure!  Of course, the most memorable part was when the “boys” made their big catches and solved the dinner problem for the next few nights. Tim caught a delicious mackerel and Shay hooked a shark!  We got to keep both, but had to toss back the numerous other fish that were deemed too small to keep.

We drove the last leg of our trip and arrived at our condo in Kissimmee, Florida late in the evening.

Days 7 to 14:

We had rented a condo that would serve as our home base for our week stay in Florida. During our time in Florida, we did a variety of touristy types of activities. We had taken the kids to Disney twice before, so although we did spend one day enjoying the parks, it was not the highlight of our trip. Here is a bit of a summary of what we did.

  • We spent the day at Aquatica, and on this trip everyone was “big enough” to try all the watersides. Our kids love Aquatica and deem it their favourite water park. What fun!!
  • The next two days were enjoyed at Universal Studios.  Eden was more cautious and opted out of most of the thrill rides, but Shay was more adventurous and joined us on most of the coasters and other attractions.  The water rides were a big hit with the whole family, as the days were very hot.  Despite the crowds, the lines moved quickly and both days were great fun!
  • We decided to take a day to enjoy the pool at the condo, shop Downtown Disney and go miniature golfing at Pirate’s Cove.  We had a great time golfing, and Tim and I reminisced about the first time we had golfed there, about 20 years prior.  I must admit I had the most fun because I waxed Tim and the kids!! (I’m very competitive.)
  • We could only squeeze in one day at Disney, so we splurged and got park hopper passes.  The kids participated in the Jedi training at Hollywood Studios.  We hit all of our favourite thrill rides at both Hollywood Studios and Epcot.  It was a long day, but great fun!
  • Our last day in Kissimmee was spent at the Discovery Cove all-inclusive resort.  We spent the day snorkelling and swimming with a variety of tropical fish, stingrays and of course, the highlight, dolphins.  We got tomeet Kylani.  She had great personality and enjoyed our hugs and kisses!   Kylani’s aunt (a full grown dolphin) let us hold her fin and took us for a ride.  It was a truly awesome experience and a day we’ll never forget.


After a wonderful day at Discovery Cove, we got back on the road to begin our return trip. We stayed at the John Denham House in Monticello, Florida. The home was built in 1872 and oozes with character.  We had a peaceful sleep in the infamous “blue room” despite the fact the home was named the “2nd most haunted place to sleep with a ghost” in USA Today. The 12 foot ceilings and massive pocket doors made Tim look like a dwarf in comparison.

Day 15

We drove along the Gulf coast and saw first hand the lingering devastation of “Katrina” (2005) along the deserted shore.  We arrived in New Orleans on the 6th anniversary of the hurricane.

Once in town, you couldn’t help but enjoy the music and excitement of Bourbon Street and the French Quarter.   We stayed in the beautiful Hotel Monteleone which was built in 1886.  Tim and I had Po’boys at Mother’s and of course, we stopped for coffee and beignet at Cafe du Monde.

Days 16 and 17

From New Orleans we headed West to San Antonio, Texas, where we spent two days.  We stayed at another lovely bed and breakfast – Bonner Garden.  This grand Italian Villa was built in 1910.  During our stay, we spent time in the private pool, took a guided boat tour along the famous river walk, and visited  The Alamo. Bonner Garden was a great place to stay, but I understand it has been permanently closed.

Days 18 and 19

We began our return trip by driving north through the Ozarks to Eureka Springs, AK (one of our favourite places).  I’ve added a link to the Eureka site, but if you Google Eureka Springs images, you’ll soon see why we love it! I first heard of this quaint one of a kind town in the early 1990’s. Tim and I stopped there for the first time over 20 years ago and instantly fell in love with it. I think this was my fifth trip through Eureka Springs. I absolutely love, love, love Eureka Springs.   For more on Eureka Springs, check out this articleOf course, we stopped at Bubba’s BBQ for their famous ribs before heading to our hotel.  (If the truth be told, this is one of the reasons we stop here.) To be honest, the hotels we stayed in were not really that nice, but we were doing the “historic” theme and decided to try two iconic Eureka hotels: the Basin Park and Crescent Hotel. They were fine, but would probably stay elsewhere next time. There are many lovely choices in Eureka Springs.

Eureka Springs must be one of the quaintest towns in North America.  It is nestled in the Ozarks and the streets and buildings are built right on the side of the mountain.  The town is very old and each and every building tells a story of long ago.  It is home to many artisans, and the main street is lined with unique little boutiques.  We spent our day getting “old time” family photos taken, visiting the Thorncrown Chapel and “Quigley’s Castle”, shopping, eating at “The Dog house” and having the best dessert ever at “Peace, Love and Cheesecake”. The town is just so cool…lush trees, hilly townscape, incredible architecture, character homes and unique boutiques and eateries… really has it all. In fact, Eureka Springs would make a great road trip destination as there is so much to explore in the area.

Day 20

From Eureka, we headed to Kansas City, where we spent several hours shopping at the outlet mall. We came back to the van to find a note under our wiper that said, “Go Jets Go! from a fellow Manitoban”.  We had an awesome burger at FIVE GUYS and then continued driving to Sioux Falls, SD.  It took much longer than expected because sections of the interstate were still closed due to spring flooding.  We arrived in Sioux Falls very late and got a room for the night. We tackled the last 7 1/2 hours the following day, and arrived home around 5 o’clock on the 21st day of our trip.

Despite the many hours spent in the van, the memories and experiences have been unparalleled to date. There was so much packed into those 3 weeks. Again, I say to you…..take the plunge and plan a road trip. There truly is nothing like it. For more information on why road trips make the best family vacations and the steps to planning a successful trip check out my previous posts.

11 Steps to Planning a Successful Road Trip

Why a Road Trip?

11 Steps to Planning a Successful Road Trip

Road TripIn 2011, our family embarked on a fabulous 17 day road trip. I’m pretty organized and must say that the thought of spending endless hours in the vehicle with two young children both excited and terrified me. At times, I thought the whole idea was ludacrist, as we couldn’t seem to make it across the city to piano lessons without a royal battle commencing in the backseat. We had been on many 4 hour drives to my hometown and although the kids did occassionally “fight”, it seemed like scooting around the city was more of an issue than when we were in “vacation” mode. I was cautiously optomistic, but the teacher in me decided that the best way to ensure survival was to plan lots of activiites for the van. I can honestly say I must have spent about 50 hours or more planning this trip. Some of the time was well worth the effort, but some was an absolutet waste of time. Let’s just say I learned a lot from planning that first big trip.

At the time, our kids were 9 and 7. They owned iPod shuffles that had their own music on them, but did not own or have access to any kind of “device” to occupy them with video games, so it was up to me to figure out how to fill the 100 hours we expected to be on the road. Yep, that’s right 100 hours, (10,000 km) in 17 days!  Our days on the road averaged at around 7 to 8 hours per day, but we did do a couple of 11 hour days as well as some short trecks as well. The trip was packed with long days of travel, pit stops and lots of adventure.

Planning the travel details like the route, places to stay and major attractions was well worth the time and effort. Likewise, the bit of research I did about the 22 states we travelled through kept us entertained and counting down the miles to the next stateline. The kids were intrigued by the fun facts and trivia we learned along the way. I also think it helped that the places in which we stayed were in some way intriguing in and of themselves. We stayed at several Bed & Breakfasts, many of which were historical homes with lots of history. The kids enjoyed meeting the owners and learning about the homes and towns we visited, just as much as Tim and I did. I really strived to stay away from the hotel strips and find quaint little towns or neighborhoods within the areas we wished to stop.

On the flip side, the crate full of activities I researched, made, purchased and collected was for the most part an absolute waste of my time. I had travel bingo games, card games, sketch books, books to read and numerous other activities. The crate full of “time killers” was big, took up lots of room and was virtually untouched. I totally underestimated my kids. There were exactly two conflicts/meltdowns on the trip….and both were after long days during our week stay in Florida (not on the road). There was not one single dispute or complaint during the entire drive. I did make the kids passports with the intention that we would collect ticket stubs, stickers, etc. along the trip to add to their passports. I thought this was a great idea (and still think it is), but we honestly just kind of forgot about them, as we were too busy having a great time! The sketch books and maps were the two things the kids used.

11 Steps to Planning a Successful Roadtrip:

  1. mapMind Set ~ set the stage for a positive road trip.  Although we planned to spend one week of our vacation in Florida, we never talked about our trip in terms of a “trip to Florida”. It was never about the destination, but rather the adventure of being on a road trip with many stops and adventures along the route. I think this really helps to eliminate the “how long until were there mentality”.
  2. Map out your route and make copies for the kids. Our kids loved highlighting our route as we travelled and enjoyed filling in points of interest and personal memories on their own maps.
  3. Take a GPS. If you don’t have one, it really is a must. We visited lots of little towns and it was so simple to find the addresses of the Bed & Breakfasts with our GPS. I assume most people have one or access through their phones, but it really is a necessity if you don’t have one.
  4. Take your vehicle in for servicing before you go.  Be sure all the fluids are full, tires are in good condition and that your vehicle has been completely checked over (especially if its an older vehicle).
  5. Find interesting facts about the states or areas you plan to travel through. We passed through 22 states in 17 days. As we crossed each state line, I would share some interesting facts about each state. The kids’ favourites were learning what famous people live in or came from a particular state, town or city. They also loved the crazy list of 3 or 4 state laws I managed to did up. These took the form of “Did you know it is illegal to _____ in _____?” (For example, “Did you know it’s illegal to cross the state line with a duck atop your head in Minnesota?”) Of course, there is a website completely dedicated to sharing dumb laws, so its pretty easy research and lots of fun for the whole family. Another favourite was learning about popular foods or “dishes” in certain states. Whenever possible, we tried to sample some foods that were either grown in or unique to certain areas. (Like the Fried Green Tomatoes and Peach Pie in Georgia or a Po-Boy Sandwich in New Orleans. Mmmm.)
  6. Try to plan your stops ahead of time. This gives you a goal for each day and by pre-planning, you don’t have to worry about finding a decent place to stay. We wanted to maximize our time at our stops, so we planned a few long driving days. This allowed us spend more time in the places we really wanted to explore. My husband loves to drive and he was more than happy to do all of the driving. Pre-booking your accomodations can also help the budget, as there is nothing worse than breaking the bank on an unplanned expensive hotel stay because you’re in a “pickle” and can’t find anything else.
  7. Entertainment: We did have a DVD player in the van, but our kids only watched one movie, twice. We were going to visit Universal Studios and neither of them really knew the Harry Potter series, so we bought the first movie for the trip. We took a whack of others, but they were too engrossed in the trip to watch movies. Go figure? There was no “shut-eye” either. With so much to see everyone was wide awake. Eden did not fall asleep once and Shay slept for about an hour on the last leg of our 100 hour road trip. Now that’s a road trip!!  I loved that they did not have video games. We spent the entire trip listening to great music (from a pre-made iPod playlist with great tunes both old and new) and talking. To this day, the kids will often have a road trip memory when they hear a song from our playlist. It was facinating just to watch the change in topography as we travelled from state to state . We literally saw mountains, hills, plains, ocean, beaches, dessert, and forests – it was amazing!  The architecture was also intriguing. One of my favourite memories was of all the incredible barns we saw when we exited the interstate to make our way to our first Bed & Breakfast in the little town of Whitehall, WI.
  8. Columbus ZooTry to break-up the trip with some longer stops along the way. We really found that having a “fun” destination after a long day or two of travel kept everyone excited. After your stop, try to rattle off another couple of hours driving before stopping for the night. This helps to cut the driving time on some of the other days. Everyone is tired from the day’s activities and more than happy to sit and relax in the van for a few hours before calling it a day.
  9. Of course, you need to budget. Although you aren’t paying for flights, you will be paying for gas, lodging, food and entertainment. Depending on the nature of your holiday, we found that if you spend wisely on some days, you can afford to be more extravegant on others. For example, amusement park tickets are expensive, but the beach is free (other than parking). Planning ahead really pays off. Many park passes and attraction tickets are cheaper to buy online. Try to avoid paying escalated gate prices.
  10. Take a cooler. Plan snacks and food for along the way. Make sure you bring condiments like salt & pepper, mustard, ketchup and butter with you. We had a variety of fruits and healthy snacks to munch on, but also made wraps or sandwiches for lunch. On long travel days, we would sometimes breakdown and hit a fast food drive through for dinner, but this only happened a few times. Packing healthy snacks and food is super important. No one feels good if they’ve spent days on end in the car eating Cheetos and McDonald’s. This will save you money, prevent sugar lows (moody kids) and keep everyone feeling well. It also makes those occassional ice cream pit stops a highlight for the whole family.
  11. PouchPlan some activities for the kids. Again, speaking from experience, don’t over do it. Of course, this totally depends on the age and interests of your kids. Our kids were 7 and 9 at the time of this trip. If I were doing it again, I would take prepared maps, sketch books, writing and colouring tools and a chapter book each. I might also bring a couple of trivia type games or car bingo that we can all play. Movies are a good idea, although my kids weren’t interested in watching them. One thing I would suggest is some kind of a small tub and pouch to keep their things in one place. Here is an example of what ours looked like. The pouch was picked up at the dollar store and rigged it up to attach to the front seats. It kept all of their pens and markers. (This little tub sat between them and worked well. You can’t see the huge red crate with all the other activities that they didn’t even touch.) It’s Always Autumn has a great post with 20 awesome road trip ideas and there are also some great ideas on Frugal Family Times. There are many great resources on the internet, so don’t bother reinventing the wheel – it will save you lots of time and energy.

Balance is Key:

When you are planning a long vacation, you really need to create a balance between high and low cost choices. The sacrafices you make some days will allow you to go all out on other days.

Have each family member create a list of what they would like to do on the trip. Compare the lists and try to come up with a plan that balances out the inexpensive and more pricey activities.

The same can be true for meals and lodging. When we reached Florida, we rented a condo for the week. Often renting for 7 days is less expensive than paying a nightly fee. The condo also allowed us to save on food. We ate breakfast at the condo and usually packed a lunch in a cooler before leaving for the day. (Some parks will not allow coolers, so research this first.) For dinner, we did a combo of eating in and out. Little things make a big difference. For example, you could order pizza for $30 or more, or pick-up frozen pizza for under $10 to throw in the oven after a long day. You may not feel like preparing big meals, so consider simple short cuts and convenience foods like “salad kits” or canned spaghetti sauce. This may not be the way you would shop at home, but it can save you both time and money. Try to think about buying groceries to create meals that are both easy to prepare and at least somewhat nutritious. Those store roasted chickens are another great meal. For $10, you can have dinner and possibly enough leftovers for lunch the next day. It really is worth thinking through the possiblities for easy meals before you go (or while you’re on the road), as it really beats the expense of eating out everyday.

Lodging Tips:

Again, renting a place with a kitchen is a great way to extend your money when you’re on a long vacation. The other thing to consider is booking your single or two night stays at places that include breakfast. We did try to stay away from hotel chains, as we were really looking for unique experiences.  Whenever possible, we stayed at either Bed & Breakfasts or historic hotels that were built in the late 1800’s or early 1900’s. Bed & Breakfasts can be very elegant and expensive, but many are very affordable. The nice thing is that there are nearly always plenty of reviews to help you figure out what is the best fit for your family. When travelling as a family, we are basically looking for B & B’s that are safe and clean with great hosts. You can often get a feel for the hosts through the reviews. When we were booking in 2011, I was using a site that had a “family friendly” filter. Many Bed & Breakfasts are designed for adults only. If you go to, you will first want to put in your destination, dates and number of guests. Once you press search, a button for + Advanced Search will come up. You’ll want to click this and under the ammenities, select “children welcome“. This will save you lots of time as it will only give you properties that welcome families. Bed & Breakfasts are a really great way to learn about the places you travel and connect with people. We love sitting around the breakfast table and chatting with the hosts and other travellers from around the world. So interesting! The best tips and information generally come from the locals and B & B owners will often offer coupons or discounts for local attractions. I just love picking their brains ~ “If there was one thing we must see what would it be?” You often get insider tips that aren’t even in the travel brochures!

If you want to know more details about our 2011 road trip from Winnipeg, Manitoba to Florida via “the scenic route” check-out part two of this post. The post will include the route, stops, lodging and attractions we took in. Stay tuned.


If you have never taken your family on a road trip, do it. The bonding time and memories from that one trip far out weigh those from our trips to the Dells or Disney. It is truly a chance to unplug and intimately connect with your family. Conversations go deeper and life gets a whole lot richer within the confines of a car!