This Florida Inn has perfectioned the technique of an antiquated Yuletide celebration.

This Florida Inn Capably Maintains the Tradition of an Ancient-Style Christmas Celebration

There aren't any commercial flights to Boca Grande, Florida, and it's unlikely they'll ever appear. Arriving on Gasparilla Island by car offers the first lesson in how you'll spend your time there - in slow mode. Typically, cruising at 35 miles per hour feels like navigating through molasses for me, but driving into the village, I actually wished to reduce my speed even more. I sensed a thrill in the air, something electrifying yet laid-back, and it seemed disrespectful to speed onto the golf cart-filled streets. I'm not the only one who feels this way.

Tina Malasics, the operations assistant and unofficial historian of The Gasparilla Inn & Club, has been making this journey every day since 1984. "I cross the bridge in the morning and just feel a change, you know?" she says.

In line with the inn's distinctive style, its location is understated yet elegant. It doesn't stand on the main road. You won't spot enormous gates or any loud signage announcing your arrival. The building (painted a soft, buttery shade of yellow) is unassuming yet stunning. "You just feel an immediate sense of 'aha,' " Malasics says with an exaggerated sigh.

Back in the early 1900s, the owner of the Charlotte Harbor and Northern Railroad decided to construct The Gasparilla Inn & Club for railroad executives. After expanding the original structure for accommodating travelers and updating the decor for a reopening in 1913, the rooms mostly remained vacant. This is where one of Malasics' favorite anecdotes about the inn begins.

The general manager at the time hailed from New England and aimed to attract visitors from that region. When he received an inquiry from a wealthy, well-known Boston widow about this luxurious Florida resort, he demanded that she provide references before she could stay at the exclusive Gasparilla Inn. After somehow managing to "fit her in" (remember, there were no guests at the time), she brought along other references who also booked trips. And the domino effect began. The inn gained fame as the winter retreat for the wealthy from the Northeast. An air of exclusivity still envelops this place; you often need good fortune on your side to secure a reservation.

Open for Business

Some hotels might find it offensive to be labeled old-fashioned, but The Gasparilla embraces it wholeheartedly. Its endearing traditions endear it to guests. Dress codes, for instance, add a sense of respect and uniqueness to the experience, far from being stuffy. And the employees stick to the rules; I witnessed two men being turned away from BZ’s, the cozy lobby bar, for wearing shorts after 6 p.m. (I loved it.) Tea is always served promptly at 4 p.m. in the afternoon, and regular guests begin milling about around 3:45 p.m., eager to claim their favorite pastry before someone else does.

The hotel is open for business each year from the first weekend of October through the Fourth of July, giving "The Old Girl," as the building was affectionately called by former owner Bayard Sharp, a little break.

Ownership of the property was passed around several times during the early 20th century, but since 1964, it has remained within the same family. Sharp made significant improvements to the property and the entire town of Boca Grande. He developed The Gasparilla Inn as the focal point of the community and set the standard for everything surrounding it. Picture a place that's as manicured as a scene from The Truman Show (without the eeriness). You won't find a big-box store, a chain restaurant, or even a stoplight, and the primary mode of transportation is via golf cart. People often leave their keys in the ignition when popping into local businesses, and it's common for dogs to have designated golf cart beds (not to be confused with their usual napping spots at home). There's a family-like atmosphere to the entire island. "Everyone knows everyone" isn't just a saying here - it's a fact. Running into that many smiling faces might seem suspicious, but it's simply an average day in Boca Grande.

Sarah Farish (Sharp's only daughter) and her husband, William, now own the property. Although she could delegate responsibilities to the employees, Farish personally oversees every decision at The Gasparilla Inn & Club.

Time for an Update

When the inn underwent a major overhaul in 2020, Farish was involved in every aspect of the redesign. A team from renowned Kemble Interiors, Inc. led the project, but Farish was the guiding force, carefully selecting each rickrack border for the pillows and approving every custom-painted backgammon table. Principal designer and Kemble Interiors founder Mimi McMakin has known and worked with Farish for so long that she jokes about being hesitant to put a date on it.

Like the Gasparilla's loyal guests, McMakin and senior designers Cece Bowman and Mackenzie Hodgson didn't view it as a commercial project but rather as a large home. Instead of stripping the building of its whimsical, pastel-hued charm and replacing it with white marble and sleek finishes, the Kemble designers preferred to refresh what was already there.

"There's a sentimentality about the inn that we’re drawn to," says Bowman. "They return year after year for a reason."

Every consideration was thoughtful, from the hand-painted vegetation adorning the lobby walls to a lounge filled with aged treasures and artwork crafted by Florida natives. The distinctive white furniture in the lobby remained, but was upholstered in fresh, traditional fabrics. The attention to detail in every nook is remarkable.

The Gasparilla Inn Beach Club underwent a significant makeover. Kemble Interiors transformed workout spaces into extravagant social areas, and West Palm Beach artist Christa Wilm decorated a floor-to-ceiling fireplace with a vibrant mosaic of seashells. Stray Dog Designs, based in Tennessee, built a massive chandelier in the shape of a school of fish for the Beach Club's dining area.

Twirls Everywhere

Farish's comprehensive strategy didn't stop at renovations. She was also carefully involved with the Christmas decorations for over 20 years. They were always designed and installed by Ian Prosser, the owner and principal designer of Botanica Design Studio. Farish preferred a traditional look, as she mentioned, "There's no glitter, really." The decorations included assorted trees within and a large one outside, as well as ample greenery and classic red bows.

Prosser aimed not to overshadow the existing decor with the Christmas finery, stating, "It should really shine on its own." He decorated the dining room with hanging orchids in wicker containers and concealed the sprinkler system using rattan to hide unsightly pipes. A traditional Christmas tree, decorated only in green and white, complemented the room instead of overpowering it.

Typically, magnolia garlands were not used (Farish found too much brown). However, at The Pink Elephant, Prosser was allowed some creative freedom with spray-painted elephants, shimmery houndstooth bows, and sparkling champagne-colored ornaments. The Pink, as regulars called it, was the more casual inn restaurant located separately from the main building. "It provides an immense amount of fun," Prosser said.

With its polite staff, cheerful interior, and delightful atmosphere, the Gasparilla Inn & Club offered an otherworldly experience any time of year. Add Christmas bows and garland, and you might begin to ponder, "Should I stay forever?" You've been warned.

Expert Advice For A True Masterpiece Tree

Ian Prosser on the tree's centerpiece

Was this page helpful? Thanks for your feedback! Tell us why!

Seek Equilibrium: He likened decorating a tree to creating a floral bouquet. Just as he would meticulously place one type of flower at a time, he does the same with ornaments. Divide your ornaments based on color, texture, or category, and place the entire category on the tree before moving on to the next.
Introduce Depth: Be mindful to avoid decorating just the outer edges. This leaves noticeable empty spaces. Enhance the look by tucking ornaments and string lights deeper into the tree, close to the trunk.
Consider Scale: Another approach Prosser's team uses for both bouquets and Christmas trees is to periodically step back and assess their work from a distance while decorating, as well as when they believe they're finished. This helps to avoid conspicuous blank spots or unbalanced sections.

How To Make The Most Of Your Island Time

Seven things to explore during your initial trip to Gasparilla

Sip on a Spicy Elephant, complete with a miniature plastic elephant on your glass, at The Pink.
Take a stroll or a ride in a golf cart along Banyan Street to view the trees.
Mingle with locals at the Boca Grande Annual Christmas Tree Lighting (visit bocagrandchristmas.com for more details).
Relax in a couch at BZ's bar for an evening and make quick friends.
Dine at The Temptation Restaurant for an old-fashioned surf and turf meal that satisfies even Nick Saban.
Break out your best tennis whites for a game of croquet, requiring adherence to the dress code.
For breakfast, order the sausage gravy and biscuits at The Outlet Restaurant at The Innlet, the Gasparilla Inn's smaller waterfront counterpart.