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!