Small City Road Trip

Back during the holidays, my boyfriend and I took a road trip from Florida to Pennsylvania to New York and back down to Florida. Instead of rushing to get to each family we decided to make a road trip out of it, the kicker, we wouldn’t stay at each place more than a few hours – unless we were sleeping there.

As anyone road tripping, we wanted to hit EVERYWHERE but we knew if we wanted to make it to Pittsburgh in time for Christmas Eve with the family, we had to limit ourselves and really fine tune this road trip – which is hard for two extremely spontaneous people.

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Our way of making it up the eastern part of the country was hitting smaller cities that we could explore for a few hours instead of feeling like we NEEDED to stay longer. Instead of going to the Nashvilles and D.C.s along the way, we explored the Chattanoogas and Lexingtons. While we did hit a few bigger cities like Philadelphia and Atlanta, we stuck to exploring for only a few hours – though most of them we are definitely planning to go back for a long weekend!

Our first day on the road we left from St. Petersburg to Atlanta, the longest stretch we would go. However, we did stop in Ocala to pick up some cold weather gear from Walmart and I kept an eye out for A Day to Remember, hoping to spot them in their home town!

Another pit stop was made at Magnolia Plantation in Georgia to pick up some hot sauces and what better way to road trip than to stop at every kitschy roadside attraction.

We left later than planned – thanks to The Witcher being released on Netflix – and arrived in Atlanta just in time for dinner!

We checked into our hotel in downtown Atlanta – thank goodness for all of Tyler’s Marriott points – and went out searching for a meal that included more than just gas station snacks.

We hopped on a rental scooter – easily the best way to travel in any city – and made our way to the restaurants and bars in Atlanta. Little did we know, Atlanta is hopping at night and we struggled to get in anywhere. Instead of waiting out the rush we kept wandering in hopes of finding a good take out spot or walk up window joint. To our pleasure, we ended up at the Centennial Olympic Park where a massive german holiday pop up village and festival was happening!

We grabbed some hot chocolate and made our way around the village, walking through the shops and pointing out cute little figurines. My Jewish side instantly ignited in happiness when we found the most massive latkes I have ever seen!

We ate our head sized latkes – Tyler got bratwursts with it – and continued on to see what else we could stuff ourselves with. The answer was giant soft pretzels, we can become totally overstuffed with some giant, German, soft pretzels.

Instead of stuffing ourselves more and having to roll back to the hotel we decided to skip out then and get a good nights sleep.

The next day we woke early to have breakfast at one of Tyler’s favorite spots, The Flying Biscuit, then headed to our next stop.

Next up was Chattanooga – one of my new favorite spots but that can be said about every stop on this road trip!

It was super cold and rainy during our time in Chattanooga, and being up on the mountain just exacerbated the weather situation but nothing could stop up from having a good time at Lookout Mountain. While there we quickly explored Point Park and learned about its significance in the Civil War – all while we were struggling to keep my tiny body from being lifted off the mountain in the wind.

The park offered up education about the area, a memorial, and extraordinary views of the city and river below. We indulged in the view until my fogged up glasses couldn’t take it anymore and made our way over the incline!

The Incline Railway is one of the top things to do while exploring Chattanooga. While riding you get to see views from each point of your mile journey down the mountainside.

When you get dropped off below you can explore the surrounding area or hop right back on to get taken back to the top.

The enticing smell of the sweet shop took us off the incline and straight to the hot chocolate… and my awesome, new ice cream dad hat.

After we drank our hot coco and took incline photos, we got on the next ride up to our car then straight out of Chattanooga to Knoxville – with a much needed stop at COOK OUT.

While still cold and rainy in Knoxville, at least we were closer to sea level to help the windchill subside.

We walked down Gay St. to the Mast General Store. You can find just about anything in this general store, but we really came to get all of the candy. We have quite the sweet tooth so we had to go and get all of our favorite classics!

We filled an entire bag of candy then continued to walk down the rainy road.

We stopped in a bar to grab a drink and buy a pint glass – something Tyler has been doing for the past year, where we buy pint glasses at all of the bars and destinations we go to.

After our drink – one drink – we got back on the road and headed to Lexington. It was dark by the time we got there so we did not visit the Kentucky Castle, as we were told to but instead explored the lively brewery and bar scene in the distillery district in Lexington.

The Distillery District is one of the hottest districts in town, it’s filled to the brim of food, beer, and, well, distilleries. Since this wasn’t our last stop of the night we had to take it easy on the drinking and only drank at two places; The Burl Arcade, where Tyler got to live out his 80s nerd dreams, and Ethereal Brewing, a hip brewery with lively nightlife.

It was hard to say goodbye to these spots and not spend the ntire night drinking and playing classic video games on the wall of TVs at The Burl Arcade.

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But, alas, we pulled ourself away from the drinks and made our way to Covington, our final stop of the night. While many like to stay in Cincinnati, we decided to stay right across the river in Covington where we could get spectacular night views of the Cincinnati.

When we woke up in the morning we crossed the border to Ohio and had breakfast First Watch in Cincinnati. We attempted to explore the city but we’ve become too much Floridians and could not handle the freezing temperatures of a midwestern morning.

This was our final road day for a while because we stayed outside of Pittsburgh for the first part of the holidays with Tyler’s family. We did explore Pittsburgh and the surrounding area but due to us being there for four days and not four hours there is so much to say about what we did. Some quick highlights from our stay in Western Pennsylvania was McConnells Mill State Park, exploring the city, and the Duquesne incline!

After we spent time with Tylers family, it was time to drive eastern to my family home in New York – although my family decided to dip out of New York the day after Christmas so we did not even see them there!

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We did stop in Scranton on our way over to New York to check out all of The Office spots in town. If it wasn’t for The Office we probably would have never visited this tiny city but now that I’ve been to the downtown I am all for people taking a trip to Scranton. You can read more about that adventure here!

Once we were in New York we stayed at my family home outside of the city for another four days instead of four hours. This was our relaxation stop since we had the entire house to ourselves and all of my moms sherpa blankets, we ended up sleeping in every day. We did make it out to the city a couple times and we mainly just drank at the bars while there – thank you MTA for having a stop right near my house.

After our drinking escapades in New York we started our trip back south to the Sunshine State!

Our first stop was Philadelphia, a major city always in reach of exploring but I had never done in the 21 years I lived in New York.

We stopped so Tyler could have a true Philly Cheesesteak. We asked my sisters fiancé where to go – he’s from the area – and told us the age old debate is Pat’s or Geno’s. We settled on Pat’s, where Tyler fell in love at first bite.

The two OGs are directly across the street from each other so you can try one or both and decide for yourself who has the best Philly Cheesesteak.

We decided to walk up 9th St for a bit after another bartender told us to, just to get the full Rocky experience. Then, as any Rocky fan in Philly has to, we raced up the Rocky Steps to the Philadelphia Museum of Art and took our Rocky photos. We didn’t take a picture with the statue since the line for a picture was longer than the line for a cheesesteak.

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After our explorations we drove right outside of DC, on the Maryland side, to spend the night with Tylers sister. We had dinner and then breakfast there then headed south to Savannah!

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One pit stop at the roadside attraction, South of the Border, then it was all Savannah!

We always heard Savannah was beautiful and such a great city, but neither of us had been. We were excited to get there on a Friday night, hoping we could catch a haunted bar crawl, but the drive got the better of us and we ended up passing out on our hotel sofa debating on if we should go out or not!

The next morning we woke excited to make up for our sleepiness! We walked down Broughton waiting for breakfast spots to open up, pointing out unique shops and walking into whatever shop was open.

Once the restaurants started opening we made our way the The Lady & Sons to have a MASSIVE brunch. After brunch we made our way around the Historic District, gazing up at the massive trees, awing at the beautifully manicured lawns in the parks, and walking through the antique shops along the river hoping we don’t fall down the steep steps to the water.

It was incredibly hard to pull ourselves away from this magnificent city, but we had furbabies waiting for us at home. This is definitely a city we haven’t seen the last of.

This road trip was amazing, and a first for me, plus my boyfriend and I were together for an entire two weeks in car and we came out loving each other even more so go us!

For anyone looking to travel to family, especially in a time like now where flying is not possible for everyone, I highly suggest making a road trip out of it. It was intimidating at first, I did not think I could do it, two weeks in a car? No way, not for me. But I did it and now I can’t wait for my next road trip!

I let my boyfriend take the reins on this one, and I love that we visited so many little cities, and never traveled more than a few hours at a time so we didn’t hate our time in the car.

What road trips have you done? Where are you planning to go next? Tell me below about your road trip memories and plans!

Follow along on social to see where I’ll be going next!

Like what you see? Email me at or DM on Instagram to set up your own adventure!

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