Longboat Key: Off The Beaten Track

If you’ve only seen Longboat Key from Gulf of Mexico Drive, you’ve missed most of it.  The true Longboat experience is found off the beaten track; along its canopied side streets, fishing its bays and bayous, and kayaking through the maze of mangrove tunnels that pass through such vintage north key neighborhoods as Longboat Village and Bayou Hammock.  The lifestyle choices—as quickly become apparent with a bit more investigation—are plentiful and pleasantly overlapping.

Gulf of Mexico Drive was once called Ringling Boulevard after the legendary business tycoon who figured so prominently in the early development of Longboat Key and the creation of its signature thoroughfare.  In the 1920’s, John Ringling became so enamored of the island, so acutely aware of its potential as a world class destination, that he purchased most of its south end. There he envisioned a grand hotel that would, in the words of the Sarasota Herald, establish “a center of brilliance and gaiety surpassing anything of its kind in the South.” Thanks to the financial challenges of the late 1920s, the hotel—a Ritz-Carlton—was never quite completed and became little more than a dangerous and ghostly eyesore. It was demolished in 1962.

Ringling’s extensive real estate holdings were eventually purchased by the Arvida Corporation in the late 1950s.  Its owner, visionary developer Arthur Vining Davis, considered finishing the hotel; but 33 years of neglect had taken its toll.  Instead, he focused on developing a master plan for Longboat Key and spent a million and a half dollars advertising it to the world. The island was evolving into a world-class community; but pockets of its rustic character—as evidenced by the quirky charm of Longboat Village—have been doted-on and lovingly preserved.  Here, the Longboat Key Center for the Arts—now affiliated with the Ringling College of Art & Design—offers an array of educational programs, exhibitions, and events to inspire creativity and invite active participation.

Davis adopted Ringling’s dream of erecting a grand hotel in a grand location on the south end of Longboat Key.  On an even more spectacular site, he built Inn on the Beach, which debuted in October 1982.  It was the crowning touch to Longboat Key Club & Resort, a world-class resort and country club where many a pampered guest—he calculated correctly—would fall in love with the island and queue-up to purchase homes and condominiums.  The resort boasts the only golfing opportunity on any of Sarasota’s barrier islands—with members and guests able to choose between two championship waterside courses—and the largest deep-water marina on Florida’s West Coast.  Just up the road, the Colony Beach and Tennis Club has long been an award-winning favorite of serious tennis players and their families.

A drive up Gulf of Mexico Drive on any given day makes you wonder if the people here ever sit still long enough to enjoy the island’s lush natural beauty.  They’re out in droves, jogging, biking, walking, rollerblading, playing tennis on numerous public courts and otherwise taking full advantage of the public parks, nature preserves and recreational facilities that generously dot the key. The Longboat Key Education Center—located mid-key at the Centre Shops—offers more than 150 non-credit programs, a lecture series, a performing arts series, one-day workshops and guided trips to points of interest throughout Southwest Florida

At the end of the day—after the sun makes its famously blazing exit over the Gulf of Mexico—recreation yields to relaxation and Longboat Key becomes a culinary smash hit. Diners from all over the area beat a path to such noteworthy eateries as Moore’s Stone Crab and Mar Vista, on the north end; Euphemia Haye, Harry’s Continental Kitchen, Pattigeorge’s and Café on the Bay located closer to mid-key, and the Dry Dock and Chart House, toward the south end.  Longboat Key Club & Resort offers its members and guests five unique restaurants, including its latest sensation, Portofino, overlooking the club’s new marina.  The casual comfort of the Monkey Bar and renowned Colony Dining Room—both inside The Colony Beach & Tennis Resort—are open to the public.  Starving for great cuisine on Longboat Key is simply not an option.

Today you needn’t be a tycoon or visionary to take advantage of the tremendous lifestyle opportunities that await home buyers on Longboat Key.  That loud noise you heard the other day might well have been the sound of jaws dropping at the news that a fully-updated, one-bedroom waterfront condominium—with a huge terrace and million-dollar view of the Gulf of Mexico—had just closed for $250,000.  Indeed, prices across the board have been substantially reduced on residential properties of every type in every neighborhood.  The best-priced opportunities in the best locations are selling-out fast with this year’s activity already outpacing last year’s.  Investment-minded buyers will no doubt wish to entertain the possibility of owning a guest suite at Inn on the Beach or The Colony, where the income potential is considerable.

For those who wish to possess the finest in new beachfront condominiums there’s the classically-inspired Positano and the soon-to-be, ultra-luxurious Bleu Claire.  In a completely different vein, at nearby White Sands of Longboat and Veranda Beach Club (further south, just across from the Avenue of the Flowers Shopping Center) you can purchase a fully furnished vacation apartment for as many weeks out of each year as you wish.

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