If you're looking for a taste of "Old Florida," look no further than Boca Grande - the stunningly traditional island that'll take you centuries away from the real world.
Disclosure: some of the links below are affiliate links. If you purchase a linked item, I will made a commission, at no extra charge to you. As an Amazon Associate, I earn from qualifying purchases.
*Updated August, 2019
Florida is a large an varied state - no matter what type of vacation you're after, chances are, you can find it somewhere in the Sunshine State!
From the best theme parks in the world to beaches packed with light beer guzzling "Spring Breakers," it's different strokes for different folks.
If you're looking for life at a slower, more refined pace - where golf carts are the main mode of transit, mint juleps are still all the rage, and you won't look out of place in a giant floppy hat, then Boca Grande is absolutely the right Florida for you.
"Can't repeat the past? Why of course you can...," Old Sport.
History of Gasparilla Island and the Gasparilla Inn
If you're anything like me, then you'll read up in "the Boca Grande book" - trying to figure out how this gorgeous place turned out the way it did. Boca Grande's earliest settlers came for the fishing, and European settlers did the same, centuries later. It wasn't until the end of the 19th century that the island started to take the form we know today. In the 1880s, phosphate was discovered on Boca Grande, and with the extension of the railroad lines into the area, came the wealthy Northern tourists who found that one of Florida's deepest ports also offered some of the state's best fishing. Tarpon is the name of the game - even today, you'll see massive tarpon displayed in restaurants: the crown jewels of decades-lost competitions (though Tarpon fishing is still common today). In the span of 10 years (1969-1979), Boca went from being the fourth busiest port in all of Florida, to having the railroad and phosphate industries abandoned and moved elsewhere.
The demise of industry did not decimate the Island, however, as the tourism industry continued to thrive.
Boca Grande's wonderfully historic hotel, The Gasparilla Inn, was built in 1911 and originally run by the railroad to attract tourists to its wholly-owned town, and has thrived in its century of life. Tourism now sustains the island's (small) economy, with seasonal and some year-round residents owning large homes on the island, in addition to the Inn (and several other hotels).
Boca Grande's famous residents have included, at least seasonally, the Bushes and a few Hepburns - along with a number of wealthy families, mostly from the North East and Midwest. Along with its Inn, it has served as a haven for tycoons such as JP Morgan, Henry Ford, Harvey Firestone, and the duPont family.
Golf carts are the main mode of transportation - and, in fact, the island has no gas station (aside from a fill-up station for boats).
Perhaps one of the most interesting pieces of Boca Grande's history is the "tall tale" that grew up behind the name "Gasparilla Island." Though the name can be seen on maps pre-dating the "arrival" of Jose Gaspar, a legendary pirate captain whose story is woven into Florida folklore, the train companies that created, grew, and cultivated Boca Grande from the ground up similarly stoked the legend of Gaspar, including the idea that his buried treasure was said to have been hidden on the Island - and had never been found! His rugged image continues to be the incongruous emblem of the Gasparilla Inn. You'll see many a banker-on-holiday sporting a fantastical needle point belt with Gaspar's image.
The Gasparilla Inn: The Heart of Boca Grande
The historic Inn's motto is "Florida the way it was meant to be," and is it ever.
With Greenbrier-esque decor, featuring massive palm leaves and a slightly over-the-top pink motif, the Inn is absolutely immaculate. It carries its century of history well - clean and traditional, a bit stuffy, but with its service every inch the well-oiled machine. Though the dress code has relaxed a bit in recent years, there still is one - you won't see a bathing suit or flimsy beach flip flop in these lobbies. And though you no longer need a personal recommendation to get a reservation, it very much retains the feel of a private club. Here you'll find turned-out families sporting their best Lilly Pulitzer, from Mom to Chip, and everyone in between, dining with retired doctors - always the tucked-in polo- and their wives - blonde bobs, cajun shrimp nails, and J. McLaughlin abound. Eccentric Yankees certainly are on display and "the business" is often the topic of conversation - and, of course, there's always an occasional famous face.
The Inn continues to be, as it has been for many years, privately owned by the Farish Family - William Farish was the former U.S. ambassador to England, while his wife is a descendant of the DuPonts. At the turn of the 21st century, speculation had raged that, with the death of Farish's father-in-law, Bayard Sharp, the Inn would be sold to a major developer or hotel chain. Thankfully, that was not the case, and the Inn retains all the charm its ever had - along with its historic quirks, such as the Pelican Room, a billiard room built for the Pelican Club - a group of wealthy fisherman who frequently the Inn and the Island in the mid 20th century.
With traditional Southern style, casual seating options abound throughout the hotel - while your fellow guests certainly do not.
Sporting its own, country club-style restaurant, an 18-hole golf course, a spa, a pool, and two gift shops, the Inn is very much the center of much of the social scene on the south end of the Island.
The Inn also owns two other restaurants in town - The Pink Elephant (more of an upscale island restaurant, without the country-club vibe of the Inn's actual restaurant), and a coffee shop, which also serves sandwiches, etc., in the downtown. And never fear - the fabled Jose Gaspar is depicted subtly, and tastefully, throughout.
Downtown Boca Grande, Florida
There's quaint, and then somewhere far beyond the usual definition of the term, is downtown Boca Grande.
It's a unique combination of small scale and high-end, resulting in a number of gorgeous clothing and home stores, a couple trinket shops, a gourmet take-out kitchen, and an incredible charity shop - where you can certainly score excellent deals on the discarded treasures of Boca's eccentric inhabitants.
The town can be fully explored with a quick walk through, but don't forget to visit the incredible Catholic church in town, Our Lady of Mercy, and picture-perfect Banyan Street - a stunning expanse of banyan trees - the most intricate and detailed trees I've ever seen. They truly look more like 6 trees and a few vines molded into one organism. A common spot for weddings (and a few Instagrammers), Banyan Street is easy enough to miss. Check out the map below before you go, unless you're lucky enough to have a guide who grew up frequenting the town, as I did.
Waterways in Boca Grande: Canals, The Gulf, and The Bay
What has drawn people to Gasparilla Island for centuries continue to do so now - easy access to water. Paying the $6 toll gets you access to three forms of water - the bay to the East, the Gulf to the West, and canals throughout the Island. We are on one of these channels, and one great way to tour the Island is to go visit some of the other canals - as we whiled away hours on the porch, many people came by on boats or stand-up paddle boards, to check out the homes (and, of course, look for manatees).
To learn more about the wonderful manatees, and to adopt or donate to protect them, check out Jimmy Buffet's charity, Save the Manatees.
Unobstructed access to the pristine beach is easy, with a number of public parks dotting the Island, providing entry to miles of sugar sand beaches (and some good shell selections!) During the week, you'll find few crowds, with people spacing themselves out and generally not posting up for the entire day. Extra points for taking your golf cart to the beach - don't worry, there's a parking lot (we biked).
Boca Grande is a remarkable combination of luxury and relaxation, history and style, discretion and class, that remains as pristine, yet fascinating, as it has been for a century. Hop in your time machine, stop by, stay a while, and experience this unique Floridian treasure.
"So we beat on, boats against the current, borne ceaselessly into the past."
Love it? Pin it!
This website uses marketing and tracking technologies. Opting out of this will opt you out of all cookies, except for those needed to run the website. Note that some products may not work as well without tracking cookies.Opt Out of Cookies