Holiday in the Sun

By Cindy Cole | Photography courtesy of Cindy Cole Fine Homes

I believe that the story of a place is best told by its dwellings. Whether a perfectly planned neighborhood or a single home carefully crafted to match the area’s natural aesthetic, real estate will make known the cadence of a community.

Homes all over the Emerald Coast are by-products of the lives they represent. Tuscan estates with perfectly manicured lawns and blooming buds signify year-round residents, likely retired. Courtyard-centered, high-density neighborhoods attract city dwellers who have come for an escape but still want an urban feel.

On Destin’s Holiday Isle, its residents, culture, and recreation are, as my theory proposes, as varied as the houses. This rare three-mile-long and half-mile-wide peninsula bordered by beach, harbor, and pass and intersected with man-made canals is organically grown. It still manages to exist without a predetermined path and certainly without limitations.

Where else could I relax on a balcony overlooking fishing
boats headed out to the Gulf, bike ride with a group of local guys,
hang out at the beach with the kids, and enjoy an afternoon ride
in my boat—all without getting in my car?

Holiday Isle’s charmed and weathered seaside cottages are virtually unchanged since their inception in the early 1970s. Their owners choose to embrace a simpler time. Study its warm-colored Mediterranean estates, and you imagine celebrations of cheerful guests connecting over blue-green seas. Modernist masterpieces overlooking high sea dunes begin to fill in blank spaces, offering a hint at progressive thinking and an acceptance of new ideas.

Residents like vacation home–owner Bill Smith, who spends most weekends with his wife in their Waterview Towers Yacht Club condominium, came to Holiday Isle looking for adventure. Waterview Towers units embrace the sprawling space of their 1990s architecture, but most, like the Smiths’, have been updated in today’s finishes and colors. The building overlooks Destin’s East Pass, which links the harbor to the Gulf and its rocky jetties. The Smiths take in one of Destin’s most spectacular views through floor-to-ceiling windows.

My family and I would never leave Holiday Isle,” Bill says. “Where else could I relax on a balcony overlooking fishing boats headed out to the Gulf, bike ride with a group of local guys, hang out at the beach with the kids, and enjoy an afternoon ride in my boat—all without getting in my car?”

With the exception of two public access points, Holiday Isle’s seductive, sugar-white beaches are private to homeowners and their guests. There are no restaurants or retail sites on Holiday Isle, and there is virtually no traffic. Trendy establishments, like Bric à Brac—a sister restaurant to Grayton Beach’s Red Bar—and Capriccio Cafe, have started to claim spaces just up the road.

Homes on the harbor find their most important calling in providing safe port for the fishing vessels that line Holiday Isle’s shore. Retro-modern newcomers coexist harmoniously with low-slung ranches, and yachts nod a respectful passage to well-intended dinghies.

David and Julie Schneider of the Cincinnati area have been vacationing in Destin for more than twenty years. In 2013, they stumbled across Holiday Isle for the first time. Their nine-thousand-square-foot glass and concrete contemporary compound overlooking the Gulf of Mexico is under construction. “Julie is an award-winning builder back home. We are almost empty nesters, so we were ready for our dream home, but it had to be big enough for all of our kids to visit. Julie had a dream for a home where every room faced the Gulf. My only requirements were peace and solitude,” David says. “When we stumbled across Holiday Isle and this one-hundred-foot lot, we knew we had found our sanctuary.”

Architect Lance Baxter designed the Schneider’s home so that outdoor and indoor spaces blend seamlessly. Telescoping walls of glass open to a dramatic lagoon-style pool with a fire feature, all overlooking alluring beaches. The home includes seven bedrooms, a game room, a screening room, and a climate-controlled wine cellar.

There is a certain sense of ease that envelops people on this island that isn’t really an island. They slow down a bit and smile before pausing to remember why. Even on the busier harbor side, the carefree overwhelms the eventful.

For a year, my husband and I lived on the harbor side of Holiday Isle. From our back balcony, we watched sun-worn fishermen clean their boats in well-rehearsed motion. Excited children checked their traps for the day’s catch that was seldom captured. From our front balcony, there were mesmeric sunsets that lingered for hours, tour boats with guides telling stories over their loudspeakers that we never heard anywhere else, and antique planes with pilots who risked their lives for the love of the show.

Homes on the harbor find their most important calling in providing safe port for the fishing vessels that line Holiday Isle’s shore. Retro-modern newcomers coexist harmoniously with low-slung ranches, and yachts nod a respectful passage to well-intended dinghies.

Cynthia Wilson has lovingly renovated two homes on Destin’s harbor front. Cynthia says, “That harbor provided an endless playground for my sons.” Cynthia’s iconic Mediterranean home on Lagoon Drive is for sale. It includes four deep-water boat slips, one large enough to accommodate a one-hundred-plus-foot boat.

Longtime residents are passionate about Holiday Isle’s history and are intent on maintaining its slower pace of life. While there is an ongoing attempt to limit the number of people who may occupy a house operated as a vacation rental, locals don’t seem to mind when a few admirers drop in on their clandestine serenity.It is amazing how architecture seems to work together with the natural inspiration of only the sun, the moon, and the sand. This island of random people and places appears to have relegated class and status to the fishermen comparing the sizes of their catches. 

With ten new housing starts on Holiday Isle in the past year, island life seems to be catching on again. The essence of its new homes remains as interestingly unintentional as the spirit of its older ones. I’m sure that the residents of Holiday Isle would love the chance to show you a glimpse of their eternally charmed lives. For your own study in island lifestyles through architecture, try a Sunday drive through Destin’s Holiday Isle.

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Cindy Cole is a broker associate with Cindy Cole Fine Homes of Keller Williams Luxury Real Estate International.