Leaving Florida, we continued north to Savannah, Georgia, a city that until 2 hours earlier we had never, ever spoken it’s name.

On paper it has some of the best charm, nature and diversity one can ask for. But we simply didn’t fit in.

Like an art student in a room full of jocks, it was obvious we had nothing in common with the locals. Despite the city bustling with life at 11:00 pm, the pub and beer culture just wasn’t our scene.

We loved and appreciated the kindness, accents and fact that every passerby said “Hi there!” while walking their dog, but we couldn’t help but lack connection. Just like love often has no explanation, so does the feeling of home. And it simply wasn’t there.

One night was enough and we continued to Charleston, the prized city of the south. Had we been simply on “vacation” we may have enjoyed a few days, even a week in the extremely quaint city, however it was more of the same from Savannah.

It didn’t take us long to admit: the South just wasn’t our place. There was just too much monotony: of food, people (it’s not international, nor are there even people from all parts of the U.S), and style. Too much of one thing, even a good thing is still too much.

And so we left, grateful for the experience. When we visit a city we learn so much more than just our specific feelings toward that city, but our feelings in general. What things do we value in a home? How did our experience here help determine what we like and don’t like?

In Charleston, and all of the south, it’s simply too disconnected. Driving from Savannah to Charleston made us feel trapped and isolated. Even though Charleston is great, with a walk score of 93, when one has to leave it takes 3 hours to get to the nearest town, which apparently are equally uniform in style.
Everyone and everything it seemed, between NYC and Florida was quite similar…. which wouldn’t be a big deal if our lifestyle wasn’t so different and unconventional.

Without even meeting that many people, we could just tell we wouldn’t be understood or have like minded people to surround us with.

We not only eliminated Nashville and Wilmington from the list, but we confined our search to well connected, open minded and diverse metropolitan locations or cities with some tourist appeal so there’s always something going on.

We don’t want to feel out of place for having a 4:00 pm lunch on a Tuesday, or going to the gym at 10:00 am on a Friday.

And so, the journey continues, us still unsure if what we are looking for is even something we truly want.

– Me

7 days, 6 nights, 10 cities (West Palm Beach, Delray, Boca Raton, Ft. Lauderdale, Naples, Sarasota, Sanibel Island, St. Petersburg, Tampa Bay and Orlando), and 1,500 miles sum up our road trip across Florida.

All in search of one thing: Home.

As we continue our search we continue to refine what we want out of a place to live. Florida is a stark contrast to the high priced, low value living of New York.

We immediately fell in love with West Palm Beach. The bustling farmers market – one of the best in the world – was our first contact with the city. We connected with the laid back, yet simultaneously energetic vibe of the beach life. Although a bit touristy, especially in January, WPB had personality.

With a serious latin influence and people migrating from all over the country in search of warm weather and low cost of living, WPB is quite diverse and offers an incredible selection of food. Perhaps it’s due to the fact that it’s extremely well connected. With 3 international airports within a 1 hour drive (Miami, Ft. Lauderdale and WPB) and a high speed railway that will take you to Miami in under an hour, it’s perfect for our jet-settling lifestyle. Even if one wants to stay close they have options. Delray Beach, a hip and happening beach town, and Boca Raton – especially Mizner Park – are just minutes away and equally spectacular.

Looking at property is always a telling moment, and here’s when we really felt like we could someday call this place home. We saw a 6 bedroom, 4 bathroom house on 3 stories for $289,500, just a short bike ride from town. Granted it needed some work but compared to the usurious prices and taxes of California and NYC, it was hard not to be attracted to the place.

This cheaper lifestyle seemed to transverse all aspects of ones lifestyle, from gas prices under $2.00 to reasonably priced organic vegetables.
… the only thing we left wondering was, why weren’t more people living here?

It saddened us to leave the next morning. But Delray and Boca Raton were calling.

On paper Delray Beach has everything: a vibrant downtown, easy access to the water and many of the perks of WPB. However, after looking at property and spending some time there, it just didn’t feel like home.
We left after a day.

Boca Raton was cool – including one of the world’s best Whole Foods, but lacked the downtown walkability that was so prevalent in WPB. We continued on to Ft. Lauderdale, only to drive through realizing that it was too busy and trafficked for our taste.

Which took us to the West Coast, with promises of the countries most beautiful waters and beaches.
And it delivered.

When we arrived in Naples, we almost cried witnessing the pearly white sand and the way the water glowed in the sunset. We truly didn’t want to leave the quaint, mesmerizing downtown, and we may not have if the real estate agent hadn’t told us that the barrier to enter was over $1,000,000.

The rest of the city was spread out and full of old people – we literally looked in a 55+ community, which, is as depressing as it sounds – and so, after one night we left.

The only thing the rest of the West Coast offered was made us realize we liked the East Coast. Sarasota, Clearwater, St. Petersburg and Tampa are all painfully old and rather dull. We drove through quickly before making our way to Orlando, “wife’s” former home, before “me”.

It’s not the same as when we were there before, because being in a different part of your life makes you see the same reality differently. We were surprised at how much and how quickly we fell in love with the charming Winter Park, a high end community nestled in the north-east of the terribly trafficked Orlando.

Walking through the eclectic shops and beautiful nature, with lush Spanish moss covering the trees with its hanging tentacles, one gets completely lost in it’s beauty. It didn’t hurt that we found our absolute dream home – a 4 bedroom, 3.5 bedroom palace of 3,500 square feet, just a few short steps from the town’s center.

It both scared and confused us.

Were we ready for such a purchase? What would we use it for? Could the same money be spent elsewhere for investments while we flexibly rent in the mean time?

When it came time to actually moving forward, we got cold feet. Maybe a huge, high maintenance home isn’t what we wanted after all. Is it really valuable to own a home, or was it more likely that the home would end up owning us?

Trusting our inclination, yet certain to return to Winter Park, we opted to continue on our journey, except this time with newfound insight. It made us realize that WPB was more of a place where one can come and go… the high tourism population meant the city didn’t hold you down.
Winter Park was different – a family lifestyle and big home was something the city begged. If and when we ever get there, at least we’ll have a good place to be.

For more house hunting videos, check out our YouTube Chanel!

We absolutely love it here. It’s a bold statement to call something the best, but Manhattan just may earn the title. From the diversity (on one corner in Chinatown they sell Peking Duck, and directly across in Little Italy it’s Parmigiano Reggiano), the incredible efficiency (even Whole Food delivers), to the accessibility, NYC has something for everyone.

We could put up with the freezing cold… shivering our ass off strolling through the charming streets of the West Village still beats the 0 walk score solitary confinement that comprises most of America.

The city truly does never a sleep: an epic protest across the street lasted throughout our 20 day stay, and the ambulances and fire trucks seemed to opt for our street to transverse Manhattan. That’s okay though, it kept us out and about instead of idling on the computer.

But when it came time to viewing places to actually live our opinion changed. A 700 square foot condo that costs $2,000 a month to maintain for 1.3 million? It’s telling when it feels like a bargain to rent the same place for $5,000 per month.

And what if you have kids?

Three strikes and you’re out.

Temporarily that is. If we ever accumulate 10,000,000 dollars, 2 will surely be punted on that epic high rise overlooking the most incredible city on the planet. Even if the kids have to sleep in the kitchen.