How Financial Freedom Lets You Say ‘Yes’ to a Spontaneous 2-Week Road Trip—Without Stressing About Money
This past fall, I embarked on a two-week spontaneous road trip that turned into one of the most refreshing, free-spirited adventures I've ever had. Sometimes, the best trips aren’t the ones that are meticulously planned—they're the ones that unfold as you go, filled with unexpected stops, new experiences, and a sense of freedom that’s hard to replicate in everyday life.
Imagine waking up on a Monday morning, looking at your calendar, and realizing—you have nothing tying you down. No clocking into a 9-to-5, no financial stress looming over your head, and nothing stopping you from packing a bag, grabbing your keys, and hitting the road for two weeks of adventure. That’s exactly what financial freedom has allowed me to do.
It all started with a smart decision: buying a starter condo. While many people aim for a big house right away, I chose something smaller, more affordable, and easier to maintain. The lower monthly costs of owning a condo—like reduced utilities, lower maintenance, and minimal overhead—have freed up my finances in ways I never expected. Instead of feeling weighed down by an expensive mortgage or endless home projects, I get to use that extra money to invest in experiences, like spontaneous road trips that don’t require months of budgeting.
The journey began with a simple thought: why not hit the road? And so, without a detailed itinerary or specific destinations in mind, I packed up my dog, Buttercup, and set out from Chicago. With no rush to get anywhere, the trip was all about enjoying the moments, exploring new places, and taking it slow.
First Stop: Murfreesboro, Tennessee – A Tiny Farm Stay
After a long day on the road, I made my first stop in Murfreesboro, Tennessee, at the most charming Airbnb I could have imagined. Nestled on a tiny farm, the property was surrounded by rolling hills, and it felt like stepping into another world—peaceful, quiet, and rustic. The best part? The hosts had fresh farm eggs waiting for me, and there were chickens and roosters roaming around, adding to the country charm.
Waking up to the sound of roosters crowing and enjoying breakfast with farm-fresh eggs made for a perfect start to my trip. It was a reminder of how rewarding it can be to disconnect from the hustle and bustle of daily life and embrace the simplicity of nature.
Lake Buena Vista, Florida – Disney World, Great Amenities, and Dog-Friendly Comfort
After a few days of enjoying Murfreesboro, I continued my journey south, eventually arriving at Lake Buena Vista, just outside of Disney World. I stayed in a lovely dog-friendly hotel that had everything I needed for a comfortable and relaxing stay. The property boasted a fantastic pool and a fully-equipped gym, which was perfect for unwinding after a long day of exploring the parks. The best part was that it was just a short distance from Disney World, so I could easily head to the parks each day and make the most of my time there.
Each morning, I would make tea with Buttercup by my side and plan the day’s adventures—whether it was spending the day at one of the Disney parks or exploring the outer suburbs of Orlando. The hotel was cozy, and the fact that Buttercup could stay with me made it feel even more like home. I was able to enjoy the magic of Disney World each day while having a peaceful, comfortable place to come back to in the evenings.
When I wasn’t at the parks, I took time to explore the natural springs and manatee sanctuaries in the area. These hidden gems provided a much-needed contrast to the bustling theme parks, offering a serene environment to enjoy the natural beauty of Florida. The trip was all about balance—mixing adventure and relaxation, theme parks and nature.
Some local spots in the Orlando area worth visiting for natural springs include:
Wekiwa Springs State Park: Just a short drive from Orlando, this park offers crystal-clear springs perfect for swimming, kayaking, and hiking. The peaceful surroundings make it a fantastic place to relax and enjoy Florida’s natural beauty.
Blue Spring State Park: Known for its manatee sightings, Blue Spring is a stunning spot for wildlife lovers. The park is also great for tubing, paddleboarding, and enjoying the lush, scenic views.
De Leon Springs State Park: This spring has a unique charm, complete with a pancake house right on the water. It’s a perfect spot to enjoy breakfast after a swim in the spring or a canoe ride.
A Visit to Friends in Alabama
On the way back up north, I took a few days to visit some friends in Alabama. We caught up, had great conversations, and explored some local spots. It was a much-needed pause before continuing my journey, and it made the trip even more special to be able to connect with loved ones along the way.
Brentwood, Tennessee – A Final Rest Stop with Local Flavor
Before heading back to Chicago, I made one last stop in Brentwood, Tennessee, just outside of Nashville. Brentwood is known for its scenic views and vibrant local businesses, making it a great place to unwind and enjoy some local charm. The town’s small but impressive selection of independent spots is what really makes it stand out.
Dining: For a delicious and upscale dining experience, I highly recommend Kerrington Rowe, a modern American restaurant with an elegant atmosphere and a menu full of flavorful, creative dishes. Whether you're in the mood for a fresh seafood dish or a perfectly cooked steak, Kerrington Rowe delivers a great dining experience. Another excellent choice is Del Frisco's Grille, where you’ll find a refined yet casual ambiance and a menu that’s sure to satisfy. From classic American fare to craft cocktails, it’s the perfect spot for a night out or a leisurely dinner with friends.
Shopping: For a memorable shopping experience, make sure to visit Hemline Brentwood, a fabulous local boutique that carries an eclectic mix of women’s fashion, accessories, and unique gifts. Whether you're looking for the perfect outfit, a trendy accessory, or just want to support local businesses, Hemline is a must-stop shop in Brentwood.
More Local Spots: If you're a coffee lover, The Coffee House at Second and Bridge is an absolute gem, offering freshly brewed coffee and cozy vibes. It’s perfect for sipping on a cup of joe before you hit the road. For a more relaxed shopping experience, head to Downtown Franklin, for a variety of stores, from boutique shops to well-known brands, giving you the perfect opportunity to find something special. Whether you're on the hunt for the latest fashion trends or looking for unique gifts, Franklin is the place to go for a pleasant, relaxed shopping spree.
The Freedom of the Open Road
What made this road trip truly unforgettable wasn’t just the destinations or the places I stayed. It was the freedom to go slow and savor each part of the journey. Traveling spontaneously allowed me to embrace flexibility, make decisions on a whim, and truly enjoy each day as it came.
Whether it was exploring a new town, having quiet mornings with Buttercup, or taking an unplanned detour down a scenic road, I realized how liberating it is to not be tied down to a set schedule. The memories I made—from the farm fresh eggs in Tennessee to the sunsets over the manatee sanctuaries in Florida—will stay with me forever, reminding me that sometimes the best adventures are the ones you don’t plan.
If you’re thinking about taking a road trip or simply going on a spontaneous adventure, I can’t recommend it enough. There’s something incredibly refreshing about taking the time to slow down, breathe, and enjoy life’s little moments on the road. After all, it’s not just about the destination—it’s about the journey.