Road Trip Simply

Howdy, road warriors! Welcome to #RoadTripSimply, the Road Trip section of Simply St. Augustine. If this is your first time here, you may want to start by learning about me. At least that’s what I do when I visit new sites… I like to know who is writing so I know if I’d like to do things their way! I love brainstorming road trip ideas- read some of our actual trips below!


If you’re coming to St. Augustine and need help planning your time here, go straight to Simply St. Augustine where you can learn about local dining, what to do, parks in St Augustine and tons more. If you’re planning a #RoadTrip, stay on this page. Road Trip Tips are first up! I’ve linked some trip ideas further down.

I have lots more planned for this page in 2017-2018! To get email updates, join 1,500 other amazing people on my mailing list. Easy peasey!

How to Road Trip with Kids

We love to travel and really immerse ourselves wherever we are. I have a saying here on Simply St. Augustine… Enjoy your stay the local way. When we’re visiting somewhere new, that’s what we try to do! Really slow down and do life “their way”. When we travel this way, we hashtag #RoadTripSimply on social. Try it as a reminder to SLOW DOWN and enjoy the ones you’re with!

I think a Road Trip begins when we pile in the car… life is about the JOURNEY, not just the DESTINATION, right?! We travel with 7 kids and we enjoy it! If you’re trying to figure out how to road trip with kids, here are some protips:

How to Survive a Road Trip with Dad

Make a Rainy Day List Before You Leave

10 {and 1/2} Tips to Road Tripping with a Baby

Pack a Mamma’s Bag-o-Tricks!

#RoadTripSimply Saint Augustine Quote

Road Trips We’ve Taken

Here’s a quick list of the Road Trips we’ve taken. Scroll down to read more about each and find links to our favorites and memories. 🙂

A Mountain Vacation in Helen, Georgia

Every year, our family retreats to the foothills of the Smoky Mountains. We’ve found our Shangri-La just outside Helen, Georgia. Every year, we explore a few new places and return to old favorites. Other than our annual girls day, we don’t spend any time in Helen itself. Instead, we’ve come to love the surrounding parks, trails and attractions for the kids. Take a look at our family favorites on this page: What to do in & around Helen, GA

st augustine road trip Writer’s Retreat to St. Simon’s Island

I’m a mamma and a writer. Sometimes those two roles fit together perfectly. I like capturing simple moments to memorialize everyday life. But sometimes being a mamma to 7 sweet children does not fit well with writing. I’m lucky to carve out 2 uninterrupted hours and when I’m writing a book or working on a big piece for a regional mag, I need quiet for hours at a time. This is where writer’s retreats come in. One of my favorites was to The King and Prince on St. Simon’s Island, Georgia. I threw open the doors to my suite and the soft murmur of the ocean provided the best white noise ever to cover distractions as I wrote.

If you’d rather spend a long weekend exploring St. Simon’s Island, The King and Prince is still a great base. This page (same as the link in the previous paragraph) outlines how I would explore Georgia’s Golden Isle: What to do in St Simons Island

Ever been to Boston in the fall? I have and I LOVED it!

Oh my gracious, y’all. I didn’t think I’d like Boston all that much. I’m usually more of a small town & quiet country roads kind of gal. Well, I was wrong. I’m also a city girl. 🙂

We went to my first professional baseball game- the Boston Redsox vs the NY Yankees at Fenway Park! We LOVED exploring the Italian restaurants of Boston’s North End and really the North End in general. We had a blast sending our kids photos with a little lobster we picked up in a cheesy souvenir shop. We deemed him Lobstah Lou {say that w/a Bostonian accent} and took pictures of Boston with him.

Back to FLORIDA… Jacksonville is a quick drive from St. Augustine!

Hardly a “Road Trip” from St. Augustine but certainly a drive if you’re not from here, metro Jacksonville offers TONS to do. Did you know it’s the largest city in the US? I’ve blogged a few things I love about Jax:

  • Casa Marina Hotel, a historic oceanfront retreat in Jacksonville Beach
  • A friend guest blogged the Jacksonville Zoo… I need to get there myself and share current faves soon!
  • Barbara Jeans Restaurant is an Old Florida, Intracoastal waterfront favorite in Ponte Vedra {If you’re looking for waterfront in St. Augustine, here’s my list of waterfront restaurants in St Augustine}
  • Another guest post featuring a drive down A1A by a friend, Gluten Free Jacksonville {If you’re looking for GF options in St. Aug, here’s my list of Gluten Free Restaurants in St Augustine}
  • And although Seasons 52 is not exclusive to Jax, I do enjoy eating off their fresh menu when hubby & I want to dress up a bit. But, more often, if we’re at the Jacksonville Town Center, we head to M Shack for some delish local burgers and great shakes!

what to do in palatka florida

Palatka is also just a Country Road Drive Away

We often pop over to Palatka to visit Ravine Gardens… the azaleas are breathtaking from Jan – March!

Amelia Island and Fernandina Beach

One of my best memories ever… a road trip up A1A with the top down {in a Corvette}. Forever in my heart = Road Trip to Amelia Island. I also loved my flight over Amelia Island– it’s a perfect place to experience powered hang gliding!

More than Disney in Orlando, Florida

We go to Orlando all the time. It’s only 2 1/2 hours away and we have BFFs there. The truth is, you could spend a year vacationing in Orlando and do something different every day. The Road Trip Orlando page is starting to fill up and I have tons more to share! Click the “vacationing in Orlando” phrase 2 sentences back for the fun!

LEGOLAND Florida Road Trip!

LEGOLAND and Old Florida in Lake Wales

If you have kids who love LEGO, you must make time for LEGOLAND. Here’s a recap of LEGOLAND photos and here are some LEGOLAND protips. Here’s how we drive to LEGOLAND from St. Augustine and a memory from nearby small town Lake Wales, which was a big deal back in its heyday. It’s a good glimpse of the changes Florida has gone through in the past 100 years.

Want to experience Mayberry? Monticello, FL is a small town with no red light!

There’s no place like home so I love taking my kids to Monticello, my hometown. It’s truly life in the slow lane… there’s not even a red light there! When we visit, we always go to Johnstons Meat Market for some sausage. We mostly cook for ourselves but every visit we eat out one meal… like at Monticello Pizza Kitchen or The Brick House Eatery. I have a twitter friend who lives over that way and has extensively food blogged the area… if you’re looking for good food in Monticello, Tallahassee or other N Florida areas, check out his site: Sweet Tea & Bourbon.

My site designer is making it where you can read the latest posts here… but it may take him a while because he’s my hubby and I don’t pay too well. 😉