Road Trip: Florida with a Newborn

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After weeks of endless snow, -30C/-22F weather and being stuck inside with a colicky newborn (hello cabin fever!), I was ready to get out of Toronto and escape to someplace warm.

I needed a hot spot that would be easy for the rest of the family to join; and one that our budget could handle. We picked Florida — specifically Fort Myers on the gulf side — for kid-friendly beaches and sunshine.

The Plan

Travelling with a newborn is unpredictable. And I was going to be travelling solo, with a baby in need of constant motion. Just the thought of packing for the plane, with her mountain of belongings, was stressing me out! This made the decision to drive easy. I could extend the trip as long as possible and share a nice leisurely drive with baby Liv.

I took the direct route down through Fort Erie and broke the drive up into four (roughly) 5.5 hour days. I knew with food stops, minimal night time sleep and baby breaks, the days would be much longer; and of course I wanted to do some sightseeing along the way. Who knows when I’ll get to visit Charlotte again?!

My itinerary:
Toronto – Pittsburgh (5 hours)
Pittsburgh – Charlotte (7 hours)
Charlotte – Jacksonville (5.5 hours)
Jacksonville – Fort Myers (5 hours)

IMG_7714The Trip

Toronto to Pittsburgh

Baby Liv and I were all set to leave on Wednesday morning. With 2300 kms to go, mother nature decided NOW would be the perfect time for a snowstorm in Toronto! And of course we’d planned to take the more treacherous mountain route down to save a bit of time. Like true Canadians, we packed up and hopped on the road anyway.

What seemed like a day later (it was 4 hours with a stop for lunch and heavy heavy snow), we finally made it to the border — lucky for us, there was zero wait and no snow on the other side.

We arrived downtown around 6 p.m., and used the Hotel Tonight app to find a sweet deal on the Shadyside of Pittsburgh. We did a quick loop down Forbes Street, passed the University and the city was hopping for a Wednesday night. After checking into Shadyside Inn Suites — a spacious 1 bedroom with an open-layout living room and kitchenette — we headed out for a stroll and some grub. The hotel recommended the Shady Grove Pub which had a huge, reasonably-priced menu and was packed at 8 p.m. Check out my shrimp tacos below!


If booking last minute, do a quick loop of the hotel neighbourhood first to make sure it’s safe and within walking distance to shops, cafes and restaurants you want to visit.

In the morning, we walked along Walnut Street and hit up Coffee Tree Roasters to fuel us for the day and stretch our legs for the drive ahead.

Pittsburgh to Charlotte

It was an EXTRA long, but gorgeous, drive today thanks to the babe. What should have been 7 hours, turned into 10 with MANY stops along the way. Caffeine was a must in my food groups today!


​If you can make it, Summerville along the I19 (3 hours from Pittsburgh) was the perfect choice for lunch, with lots of variety right off the highway and big box shopping. Gas stations were everywhere, so there was no need to worry about running low. And stopping right off the highway is ideal. We also went through a few automated toll booths looking for exact change, which luckily I had. No clue what you do otherwise, so make sure to carry some with you.

Arriving in Charlotte around 7 p.m., I booked the Hampton Inn Uptown Charlotte, which was a clean, nice size room and great location for walking. They also had a free shuttle service for nearby stops; but after being in the car all day, we were up for exploring the neighbourhood on foot.

The hotel was right next to the NASCAR Hall of Fame and close to College Street which is full of restaurants and shops — an even better place to stay if you can find a good hotel deal. We stopped in at Queen City Q for a delicious BBQ dinner, and a visit to Amélie’s French Bakery is a must. The décor, savory food and wine and beer options make it the full Parisian experience.


Everything I read about police radar through the mountains was true. By the time you see them, it’s WAY too late! Take your time, watch your speed and you’ll have an enjoyable drive.

Charlotte to Jacksonville


Hello sunshine! We finally made it south of the cold temperatures and palm trees were starting to sprout. The roads were now big, flat and dry which made the drive almost a little boring at this point! Or maybe we were just road trip pros after 3 days.

Sadly, good reviews for staying downtown Jacksonville were hard to find, so we opted for the Southside/San Marco area and came across The Aloft at Tapestry Park. Tapestry Park was a quaint, old-fashioned development with everything I needed in close walking distance (even a Starbucks in the hotel parking lot!).

For our last meal on the road, we went big and treated ourselves to a III Forks Steak and Seafood dinner. I definitely recommend the Brussel sprouts with lemon aioli.


See the city. Staying on the outskirts means you miss out on the true downtown experience. 

Jacksonville to Fort Myers

With a quick and easy last drive, we finally arrived in Fort Myers and 28C/82F weather. Now it was time to unpack, settle in and explore our new home for the month, before the rest of the family arrived.

Don’t forget to follow Practical Adventures on Instagram to catch my upcoming posts on our Florida vacation, including the drive home and seeing Graceland.

I’d love to hear from you! Leave a question or comment below about your road trips to Florida and favourite spots.


Note: All recommendations are products we have personally tested and truly love. No sponsorship was accepted for these features.

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