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Front entrance to the Gasparilla Inn located in Boca Grande on Gasparilla Island, Florida. All photos by Paul Goldfinger © 2014.   Click all photos to get bigger views.

Side view.  Condé Nast rated the Gasparilla Inn among the top resorts in Florida. The Boca Grande beach is number two of Travel and Leisure’s “best little beach towns in America.”

By Paul Goldfinger, travel editor @Blogfinger.  Re-posted from 2014.

If you were a big shot one hundred years ago, like Henry Ford, Thomas Edison or Harvey Firestone, you would have wanted a high-tone place off Florida’s Gulf Coast, where you could rendezvous in the winter with like-minded society people from the northeast who enjoyed the finer things in life.

After all, the weather here in the winter is unsurpassed. Perhaps you enjoyed golf or going deep sea fishing with your friends, but at the end of the day, you would prefer  4 star cuisine and only the best accommodations for friends and family.

Gasparilla Island seemed like the perfect place to establish a first class  hotel where the rich could mix pleasure, privacy  and business.  1,000 years ago the first visitors to the region were the Calusa Indians—fishermen who built mysterious sea shell mounds.

In the 18^th century, a Spanish pirate named Jose Gaspar plundered the waters near here. The fishing around this barrier island is remarkable, and going after the mighty tarpon is among the best sport fishing experiences in the world.

We took a ride north from Fort Myers to spend the day on the island.   There is only one way in and one way out.   The hotel was built in 1913 and is picture perfect, with the ambience of Old Florida and with a style of understated luxury.  It is on the U.S .Register of Historic Places.

People tool around in golf carts, and the town of Boca Grande, where it is located, is classy but very low key.  We had lunch al fresco in town at the Loose Caboose where they serve excellent grouper sandwiches and homemade ice cream which was a favorite of Katherine Hepburn—she even wrote about it.

Eileen (l) and  sister Hope hanging out at the Loose Caboose. Pink is an important color there—said Lilly Pulitzer.

Downtown Boca Grande. While their parents ordered lunch at the Loose Caboose, these sisters strolled across the street to learn beading.

The décor at the Inn is done in bright colors with all sorts of nautical themes around.  Pinterest.com mentions “the pinks, greens, chintz, wicker, rattan and sea shells.”  The golf course is surrounded by water, and a guest calls it “golf heaven.”  The beach club is one block away.

People here are dressed in a certain fine casual style:   Docksiders (no socks), flowery and colorful casual dresses/skirts (on the women), and khaki Bermuda shorts for the men held up with belts that have fish and lobsters on them.  You don’t see too many women in pants or short shorts or gaudy jewelry, or big hair, and not a chance of cleavage. The men like golf shirts or bright colored short sleeve polos.

The downtown is small, consisting of a few streets with restaurants and gift shops.  There is a popular store called an “outfitter” which provides fishing gear and clothing that breathes and has an spf rating .    I actually saw two guys walk in and one said to the other, “Let’s buy some really expensive gear and go fishing.”

George H.W. Bush and his family come to the Gasparilla Inn  for Christmas and New Year’s. The former president is known to be an avid golfer who goes out even in cold wet weather.  I asked a young waiter at the Inn if the locals call the shrubs “George bushes.”  He smiled but he was not enthused.

Eileen and her sister Hope were reluctant to walk into the front door. So I thought positive and entered.  They cautiously followed. Inside we walked around, and no one challenged our credentials.  The staff and guests were relaxed and easy- going. I took photos, but no one objected.     I usually don’t like  fancy places, but the Gasparilla Inn seemed just perfect to add to my bucket list.  I think I’ll start one now.

Here’s a photo tour of the Gasparilla Inn:

Living room. ©

Dining room. All light fixtures burn candles . ©

Serving tea. The staff is immaculate in dress and manners. ©

The bar. ©

Pampered dogs get chauffeured around in a golf cart.  And there is a fine and spacious dog park.

BING CROSBY  (“Puttin’ on the Ritz” was written in 1929 by Irving Berlin.)

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