Boca Grande is . . . Preppy Heaven


The Gasparilla Inn and Golf Clubhouse.


By Brian D. White


Gasparilla Island also known as Boca Grande is a seven mile long island about 45 minutes south of Sarasota, Florida.  My father’s family has been going there since the early 1920’s, traveling by train from Boston–back when you needed letters of reference to stay at the Gasparilla Inn.  My parents honeymooned there in 1961. Since I was born (and am of the fourth generation to go there) I have always felt it was in my blood and, to this day, I still spend several weeks down there with my mother every year.


Lyndsay Pond White with Brian D. White. Spending quality time with my mother every year is what it’s all about. 


We usually stay at the Boca Grande Club, which has the widest, longest stretch of beach of any club on the island. My parents joined in the early 1980’s and were among the first 100 members. One of my favorite memories at the club was always having strawberry daiquiris with my friends after our tennis lessons at the tiki bar by the pool, overlooking the beach—served by “Manuel” who is still there after all these years!


View of the beach and gulf at the Boca Grande Club.


Like membership in the Social Register or belonging to the Colonial Warriors (or Dames), going to Boca Grande Island is like the secret handshake among the super preppy set anywhere you go and you either “get it” or you don’t.


The Port Boca Lighthouse.


It’s not for everyone . . . and you are more likely to see golf carts & old bicycles tooling around the island than Bentley’s or Ferrari’s . . .  and that’s how we like it–quiet and old.


One of several churches on the island with its majestic Royal Palms.


I actually remember seeing Katharine Hepburn riding on old bicycle on the island when I was little and remember my parents being so nonchalant about it saying she rented a little place near the beach during the winter.


Shell collection by Henry Francis du Pont at the Library.


Other names that have been connected to the island for generations are the du Ponts, Sharps, Crowninshields, Bushs, Engelhards and Wanamakers, along with many from our own North Shore; once you discover Boca Grande’s special charm you are hooked and families continue coming back for generations.


The newly restored tall, skinny lighthouse: Boca Grande Entrance Rear Range Lighthouse.


During the time I’m there every year I typically go to the beach almost every single day from 10 a.m. to 5 p.m. either taking long walks from the Club up to the tall skinny lighthouse (Boca Grande Entrance Rear Range Lighthouse) and back, comb the beach for some cool shells or my favorite leisure activity–just sunbathing on the beach and going for a dip in the Gulf every hour or so to cool off.


Watching a bird hunt for food on the beach at the club while sunbathing.


We usually have lunch at the Club or run down to Newlin’s which has the best lobster rolls this side of Maine.  For dinner we alternate from an old favorite called The Temptation or “The Temp” as it’s known, with its hand painted island scenes done in the 1950’s by one of the duPonts.


Hand painted murals done in the 50’s by one of the du Ponts at “The Temp.”


Stone Crabs are still in season which I have to have at least three times along with the fresh gulf shrimp followed by the famous coconut cake for dessert.  We also go to The Pink Elephant aka “The Pink”, PJ’s Seagrille, the Boca Grande Club, and finally the historic Gasparilla Inn built in 1913, which is the focal point of the island and owned for many years by Bayard Sharp, whose wife happened to go to Pine Manor College where my mother went.


The historic Gasparilla Inn built in 1913.


In the “old days” everyone would be in coat and tie at the Inn and I’d see the most colorful Lilly Pulitzer jackets, whale embroidered pants, blue blazers, bow ties, Gucci and Belgian loafers and NEVER a pair of socks wore worn and its reassuring that some things never change and it continues to attract the preppiest people on the planet.


BDW behind the backgammon board at the Inn.


Years ago, I rallied a group of close friends from Chicago to come down for a party my family was having at the Gasparilla Inn Beach Club and during one of our nights hanging out at the Inn we came up with what we dubbed our “Triathalon of Leisure” (rhymes with pleasure) which always starts out with Gin & Tonics followed by a game of backgammon in the cocktail lounge, then dinner followed by ping pong on the porch and more G & T’s followed by a game of pool in what was then “The Pelican Club” at the Inn with after dinner drinks–all of course in a jacket and tie–I just love that title and think it sums up Boca Grande so well.


Historic Banyon Street.


It’s a totally relaxed, low key, quiet, charming little “fishing village” held back in time without over development or anything commercial about it whatsoever, with some of the most beautiful, unspoiled beaches anywhere as well as some of the best tarpon fishing in the world.

It is truly Preppy Heaven!


Sunset at 8:09 p.m.