This Historic Florida Inn Has Perfected The Art Of An Old-Fashioned Christmas

There are no commercial flights to Boca Grande, Florida, and there probably never will be. Arriving on Gasparilla Island by car offers the first lesson in how you will spend your time there—in low gear. Normally, moving at 35 miles per hour would feel like steering through molasses to me, but driving into the village, I actually wanted to dip below the speed limit. I felt a tingle in the air, something charged but relaxed at the same time, and it immediately seemed disrespectful to race onto the golf cart-laden streets. I’m not the only one who feels that way. 

Tina Malasics, operations assistant and unofficial historian of The Gasparilla Inn & Club, has been making this drive on her daily commute since 1984. “I come over the bridge in the morning and just feel a change, you know?” she says. 

In keeping with the inn’s signature aesthetic, even its location is subdued but elegant. It doesn’t sit on the main road. You won’t see lavish gates or any loud signage announcing that you’ve arrived. The building (painted a soft, buttery shade of yellow) is unimposing but stunning. “You just feel an immediate sense of ‘ah,’ ” Malasics says with an exaggerated exhale

Charlotte Harbor and Northern Railroad decided to build The Gasparilla Inn & Club for railroad executives. But after the original structure was expanded for hosting travelers and the decor was updated for a reopening in 1913, the rooms stayed mostly vacant, which is where one of Malasics’ favorite anecdotes about the inn begins. 

The general manager at the time was from New England and was hoping to reel in customers from that region. When he received a telegram from a wealthy, well-known Boston widow inquiring about this shiny new resort in Florida, he responded that she would need to send her references before she could stay at the exclusive Gasparilla Inn. After he somehow managed to “squeeze her in” (remember, there were no visitors at the time), the people she used as references also wanted to book trips. And the chain reaction began. The inn became known as the winter retreat for the wealthy from the Northeast. An air of exclusivity still envelops this place: You often need luck on your side to get a reservation. 

The Season

Some hotels would consider it an insult to be described as old-fashioned, but the Gasparilla doesn’t mind at all. Its charming traditions endear it to guests. Dress codes, for example, help make the experience here feel respectful and special, not at all stuffy. And the staff sticks 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 four o’clock in the afternoon, and regular guests begin to mill about around 3:45, waiting to snatch their favorite pastry before someone else does. 

The hotel is open each year from the first weekend of October through the Fourth of July, giving “The Old Girl,” as the building was lovingly called by former owner Bayard Sharp, a little downtime. 

Ownership was passed around several times during the early 20th century, but since 1964, it has remained within the same family. Sharp made extensive improvements to the property and the entire town of Boca Grande. He developed the Gasparilla Inn as the centerpiece 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 ducking into local businesses, and it’s common for dogs to have designated golf cart beds (not to be confused with the ones they nap on at home). There’s a familial quality to the entire island. “Everyone knows everyone” isn’t just a saying here—it’s a fact. Normally, encountering that many smiling faces might seem a bit suspect, but people are just plain happy. 

Sarah Farish (Sharp’s only daughter) and her husband, William, now own the property. Though she could easily pass off responsibilities to the employees, Farish personally approves every decision at The Gasparilla Inn & Club. 

The Interior

When the inn underwent a major renovation in 2020, Farish was involved in every aspect of the design. A team from renowned Kemble Interiors, Inc. helmed the project, but Farish was behind the scenes, handpicking each piece of rickrack bordering the pillows and approving every custompainted backgammon table. Principal designer and Kemble Interiors founder Mimi McMakin has known and worked with Farish for so many years now that she jokingly says she “hesitates to put a date on it.” 

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

“There’s a sentimentality about the inn that people are drawn to,” says Bowman. “They go back year after year for a reason.”

Every choice was thoughtful, from the hand-painted leaves that cover the walls of the lobby to a lounge room full of vintage finds and artwork by native Floridians. The lobby’s signature white furniture wasn’t replaced but re-covered in fresh yet traditional fabrics. The care that is evident in each corner is overwhelming. 

The Gasparilla Inn Beach Club had perhaps the most measurable transformation. The Kemble Interiors designers turned workout rooms into fanciful event spaces and had West Palm Beach artist Christa Wilm cover a floor-to-ceiling fireplace in a colorful collage of shells. The team behind Stray Dog Designs in Tennessee created a massive chandelier modeled after a school of fish for the Beach Club’s dining area. 

The Holiday Decor

Farish’s thorough approach didn’t end with the renovations. She’s also meticulously involved with the Christmas decorations. For more than 20 years, they have been conceptualized and installed by Ian Prosser, owner and principal designer of Botanica International Design & Decor Studio. Farish prefers to keep the holiday displays traditional, like most things at the inn. “There’s no glitter, per se,” notes Prosser with a chuckle. What he describes as “heirloomlike” touches include several trees inside (and a massive one in front of the building) along with plenty of fresh greenery and classic red bows. 

Prosser doesn’t aim for the Christmas finery to overtake the existing decor, which he says, “really needs to sing the song.” In the dining room, potted orchids hang in wicker containers, and the sprinkler system is wrapped in rattan to hide unsightly plumbing. A Christmas tree, decorated only in green and white with cascading silk orchid stems, complements this room instead of overpowering it.

Generally speaking, even magnolia garlands don’t fly here (too much brown for Farish). But at The Pink Elephant eatery, Prosser can let loose a bit with spray-painted elephants, shimmery houndstooth bows, and sparkly champagne-colored ornaments. “The Pink” (as regulars call it) is the inn’s more casual restaurant, located down the street from the main building. “It evokes a huge amount of fun,” Prosser says.

With its polite staff, cheery interiors, and charming atmosphere, The Gasparilla Inn & Club feels otherworldly any time of year. Add Christmas bows and strands of garland, and you’ll likely start thinking, “Should I stay forever?” You’ve been warned. 

How To Celebrate

Seven things to do on your first trip to Gasparilla

1. Drink a Spicy Elephant, complete with a tiny plastic pachyderm on your glass, at The Pink.
2. Take a walk or a ride in a golf cart to see the trees on Banyan Street.
3. Hang out with locals at the Boca Grande Annual Christmas Tree Lighting.
4. Sink into a sofa at BZ’s bar for an evening, and you’ll make quick friends.
5. Visit The Temptation Restaurant for an old-school surf and turf dinner that’s good enough for coach Nick Saban.
6. Pack your best tennis whites for a round of croquet. (Yes, following the dress code is required.)
7. For breakfast, order the sausage gravy and biscuits at The Outlet Restaurant at The Innlet, The Gasparilla Inn’s smaller waterfront sister site.

Ian Prosser's Advice For A Gasparilla Tree Of Your Own

Find Balance

He compares decorating a tree to creating a floral arrangement. Just as he would position each kind of flower one at a time, he does the same with ornaments. However you divide up your baubles (whether by shape, color, or texture), place the entirety of one category on the tree before moving on to the next.

Add Dimension

Be careful not to just decorate the outer edges. That can leave obvious empty spaces. Give the look more volume by also tucking ornaments and string lights deeper into the tree, close to the trunk.

Remember Scale

Another strategy Prosser’s team uses for both bouquets and Christmas trees is to routinely take a step back and view their work from afar as they go as well as when they think it’s finished. This helps prevent glaring blank spots or lopsided areas.