Four years ago, we almost moved to Jacksonville Florida, but opted to stay in New York City so that our youngest could finish high school here. We had bought a condo near Jacksonville in Ponte Vedra that has some of the best high schools in the state. We even visited schools. For native New Yorkers who have spent over four decades firmly rooted in NYC, we came really close to moving.
The almost-change significantly spurred our FIRE plans onward. If we couldn’t move right now, we wanted to be able to move to Jacksonville or another beach locale once we were empty nesters.
An Opportunity For A FIRE Trial
With our oldest having moved out and our youngest in a sleepaway camp for the first time, we were finally able to find some time for ourselves to do a trial run on empty nesting!
We drove to Jacksonville from New York City, taking the long, scenic route via the Skyline Drive, Blue Ridge Parkway, and back roads through South Carolina and Georgia where we discovered the most amazing donuts!
Rock Point Overlook – Blue Ridge Parkway milepost 10.4
In all, we spent a full week in our condo in the Riverside/Ortega area of Jacksonville. Since the trip was less a vacation and more a trial run for how we might live FIRE by moving here, I planned to work throughout the week and really see how smoothly I could move my business down here.
Can I get my work done?
Condo overlooks a park, and a tree that is currently flowering pink
I worked off the dining room table because I like the view from our living room window. We also have a desk in the corner of the living room, and I might move there long-term. Or we may outfit the now-empty third bedroom as an office for the both of us. For now, the dining room was perfect, and I got my planned work done easily.
I have a lot of variety in my work – coaching, writing, teaching, recruiting. Interestingly, I found it easy to concentrate on everything but the recruiting.
I wonder if the challenge of focusing on recruiting while in Jacksonville is the pace of life there? New York City and recruiting are faster-pace, so perhaps they just go best together? It’s a good thing for me to know this about myself as I develop business in this next year before our move.
Can I find my creature comforts?
Another item I wanted to check during our trial FIRE run in Jacksonville was whether I could get as comfortable as home. For me, that means finding no-frills, comfort food places to eat, and being able to cook my favorite Filipino dishes. On the comfort food front, we checked all the boxes:
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A truly amazing pancake!
Diner: We’re walking distance to a Metro Diner, which is great for breakfast, though they have an extensive lunch and dinner menu as well. I had a Southern pecan coffee– the pecan is in the beans, not a syrup. Delicious! Scott had the special that day, the Everything Pancake, which was ginormous and the leftovers provided breakfast for a 2nd day! Metro Diner got it’s start in Jacksonville but has expanded to 11 states now, so maybe there is one near you?
- Southern comfort: Our realtor turned us onto a great fried chicken place, Beach Road Chicken Dinners, on an earlier trip, and we confirmed on this trip it’s just as good as we remember. The restaurant is an institution and feels very vintage – it has been there since 1939, when it was literally in the middle of nowhere on the 15 mile road that goes to the beach from Jacksonville.
- Chinese: We discovered Silver Star on this trip and loved it. Not only did we find a nice sit-down Chinese place (verses takeout), but it serves yat gaw mein, which is hard to find even in New York. I haven’t had that noodle soup in many years, and it was yummy.
- Italian: We love pizza and pasta, and Italian is always one of the few cuisines our youngest one eats reliably. So we had to find a good place. Luckily, walking distance from our condo is Ale Pie House, which has an extensive menu for both pizza and pasta.
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Where you won’t leave grumpy!
Breakfast: My favorite meal of the day is breakfast, so I have to find lots of options for that. Metro Diner will be a standby, but to mix it up, there is also Maple Street Biscuit Company, Grumpy’s and Cool Moose Café. The breakfast box is also definitely checked.
Since we were only there for a week, I didn’t cook – all of the Filipino dishes I make are big stews or soups that feed a family for days. However, I did find a great Filipino grocery attached to an amazing Filipino restaurant and entertainment space called Maharlika. Seriously, there is a dance floor in the center of the restaurant!
Maharlika was like eating at a family party. We had empanadas, beef kaldareta and beef nilaga, and I’d order all of these again, except I’m dying to try everything else on the menu.
Large restaurant and dance floor at Maharlika’s
Meanwhile, we noted several turo-turo style Filipino places, and even non-Filipino places had lumpia on the menu. Right after we arrived, we stopped a Southern comfort food place called Westside Diner, and it offered lumpia on the menu, which was very authentic!
Lumpia at Westside Diner in Jacksonville
Even a steampunk restaurant, Goozlepipe and Guzzyworks, had lumpia as an appetizer. I didn’t try it there, but the shepherd’s pie is amazing, and the decorations in the place are pretty wild, with the walls lined everywhere with over a million pennies!
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So far, so good! But this blog post just got too long to finish it in one shot. Check out part 2, which covers what we found for entertainment, shopping and the beaches!
We are Scott and Caroline, 50-somethings who spent the first 20+ years of our adult lives in New York City, working traditional careers and raising 2 kids. We left full-time work in our mid-40’s for location-independent, part-time consulting projects and real estate investing, in order to create a more flexible and travel-centric lifestyle. 
Financial independence and early retirement is not something we originally focused on, but over time realized it was possible. Our free report, 
