Best Of

Most Creative Parties Ever

A look back at some of the wildest, including jail breaks, crime solving and poisonous snakes on the loose

BY February 6, 2018


Season’s greetings! We do know what month it is. But “season” means more than the holidays around here. And greetings also describe the hey-we-missed-you, how-was-your-summer sentiments expressed beginning around November, as yearlong and part-time residents reconvene for the sparkling soirees and afternoon outings, the sprints in stilettos and the barn dances in boots that make up another spin on the Southwest Florida social wheel.

We’ve flipped a few pages on the social calendar now and look forward to flipping a few more. At this point, we barely remember the party hats that welcomed 2018 and can start thinking about the chapeaux suitable for Hats for Cats in March at the Naples Yacht & Sailing Club. We think the time is right for a short intermission, to pause a moment to review some notable past happenings from the Southwest Florida history book—and perhaps draw some inspiration from them moving forward.

Many years, we saw stars as celebrities answered the call of artist Robert Rauschenberg for Arts for ACT. We’ve had many high points among the wine festival vintner dinners. And for pure quirk, we can reach back far, or not so far. What could top 2004’s geishas on stilts to celebrate the sales center opening of a condominium project (which unfortunately was felled by the housing crash)? Well, to answer that literally, once again last fall the first 80 brave souls to collect $1,500 for at-risk kids served by the Heights Foundation and the Heights Center went up 19 stories and rappelled back down the Westin Hotel in Cape Coral.

Looking back, Arts for ACT’s $4 million annual budget got boosts from Joan Rivers, Jesse Metcalf, Niecy Nash, Lauren Hutton, Tracey Ullman, Sharon Stone, Meryl Streep, Lily Tomlin and Willard Scott at the annual auction of fine art, which began in 1994 to benefit Abuse Counseling & Treatment’s services for victims of domestic violence, sexual assault and human trafficking. During the Rauschenberg Period, autumn may not have meant leaves falling from trees, but there was a definite whisper in the air as we waited for word on which celebrity would play auctioneer at the fundraiser.

Although Rauschenberg’s death in 2008 signaled an end to that parade of names, the show must go on. And it does, with high-caliber art offered at events like 2016’s Disco Ball with the Original Studio 54 Band.


Hosts worth their sea salt know that food can be a party star, too. Guests at Baconfest Naples last November found their favorite flavor in cookies, doughnuts, burgers and vodka—in a party held by the Kiwanis Club of Pelican Bay in support of local charities.

Stephanie Davis, chronicler of the local social scene since 1998, recalls the gold-rush days of the real estate boom, when developers dropped big coin at parties for prospective buyers. One celebrated the opening of the sales center for Cypress Club condos in December 2004. “It was in a big tent on the river. And the money spent on food! There was sushi, caviar, champagne—and not the kind that gives you a headache. And geisha girls on stilts!”

That wasn’t all. Ms. Davis as the Downtown Diva reported in the local daily that month that “even the porta-potties were class—think hardwood floors, mirrors and a courteous attendant (who opened the door as one entered).”

As she said recently, “Cypress Club never opened, but people still talk about how crazy that party was.

“There were a lot of real estate parties back then, lots of times in these beautiful homes they wanted to sell. Some were in Cape Coral, some Sanibel, but they would spare no expense. There was one in Cape Coral that had us all on a boat and took us from house to house. And every house had a theme. You’d go to one house and it would be all Asian fare. And the next house would have African drummers. And then back on the boat and to another house…”

The reasons for those real estate parties came and went. But since 2001, plenty of Neopolitans have counted on the Naples Winter Wine Festival and its vintner dinners for the wow factor.


In 2016, Denise and Brian Cobb and Mary Susan and J.D. Clinton assembled a cadre of well-known people with not-as-well-known talents, including Olympic gold medalist Brian Boitano as chef. He served creamy cauliflower shooters; crab and avocado crostini; and Hawaiian pulled pork sliders finished with paprika, pink Hawaiian sea salt, cumin and coriander. Plus, lobster salad or Liberty Farms duck salad with quinoa, sunchoke and dried cherries.

“Our entertainment was Franc d’Ambrosio, the longest-running Phantom of the Opera,” Denise Cobb says. Vintners came from Sonoma, California, and also worlds beyond the vines. Barbara Banke of Kendall-Jackson Wine Estates, for example, owns championship horses. “So the title of this dinner was ‘I Heard It Through the Grapevine.’ In my living room, we created a vineyard. We hung big wreaths of vines from the ceiling coming down over the tables. Because even though all these people had different things they did, they were known for something else, too. Everybody just had too much talent,” Cobb says, laughing. “It was an amazing night.”

Cobb also recalls a birthday party some years ago for engineer, entrepreneur and author Jim Holden given by his wife, Chris.

“He was very into, well, covertness,” Cobb says. “He knew so much about really unbelievable things. Like he had these binoculars that could look miles and miles out and see people on the deck of a ship. He was very cagey about how he got all these kinds of things.”

Chris Holden enlisted a friend of the couple who was an undercover police officer in Miami. As Cobb tells it, the three were out somewhere and Chris Holden stepped away to go to the restroom. A uniformed officer came and “arrested” Jim Holden and the plainclothes friend, who whispered to Jim not to give him away to the uniformed officer, who took their wallets and ID, loaded them into a cruiser and took them to jail. “And the friend says, ‘I’m going to break us out of here.’” The officer had left the keys within reach of some kind of tool the plainclothes friend had, and soon enough the pair had unlocked the cell.

“So they run out and jump into a police car and drive off,” Cobb says. “And they’re speeding. So the sirens start as more officers start chasing them. They catch them, throw them on the hood of the car and handcuff them behind their backs and tell them to turn around, and they all have balloons and say ‘Happy birthday!’”

The Holdens since have moved to Chicago, but stunts continue to play a part in Southwest Florida parties.

Last April’s “Hollywood Heist” for LARC, in partnership with McMurray & Nette of Royal Shell Real Estate, enlisted local people to populate a real-life scenario similar to a Clue game in a 13,000-square-foot house that was for sale in Fort Myers’ Gulf Harbour.

From the moment of conception—when LARC Development Director Angela Katz’s husband, Lenny, suggested a Clue theme—to the day of the party was a mere six weeks, Katz says. In that time, a script was written, props acquired and actors in place for the 150 guests, who would meet and scrutinize the behavior of Kerry Grant (Mike Dinko), Dame Hildegarde (Sunny Lubner), Fibberace (Marc Collins), Shirley Will (Tera Nicole Miller), Fluffy Lovelace (Anne Dodd), Mark Loren (as himself), Lenny Rogers (Patrick Day) and assorted others to tease out the thief of a Mark Loren original necklace.


Clearly, another ingredient for a memorable party is a cause for which Southwest Floridians have a passion, whether for the adults with intellectual and developmental disabilities served by LARC or the mainly migrant families whose children benefit from the educational pathways forged by the Immokalee Foundation.

The latter was the cause célèbre for a party from the past held by Shirlene and Bob Elkins.

Denise Cobb attended that one, too. “This is going back about 15 years,” Cobb said. “The theme was Africa. There were animals they actually brought from NGALA, the reserve in Collier County. Everybody got on a trolley, which was decorated, and they took us to a villa in Pelican Bay that was decorated like a jungle, then to Bay Colony, to a penthouse at the Brighton. And wild animals were there.

“The funny part of that story,” Cobb says, “is it was actually Shirlene’s apartment, and her husband was getting ready in the bathroom. And they had either a python or a boa constrictor in a big bag on the floor. It was probably sleeping, and Bob tripped over it. And then he started to open the bag and the thing started to move.”

That party had an unexpected meet-and-greet as well. “People in the elevator ran into these animals in cages. And the next week there was a bylaw about no exotic animals in the building. They called it the Elkins Rule.”

The party ended with guests being instructed to put on animal slippers and head to the beach for dessert. Then as they headed back to the residence, “all the alarms went off,” Cobb says.

Just a tiny bit of research in newspapers of yore turned up an Elkins-Rooney vintner dinner of 2006 with astonished guests watching Wallendas of the famous trapeze family suspended on scaffolding at least 30 feet high. At the time, guest Lynne Adams apparently said, “It’s so over-the-top. It’s so Shirlene.” We kept hearing that in our unofficial past-parties poll.


On at least one recent occasion, the memories involved Southwest Floridians but were made out of state.

“Retta Singer turned 65, and Elliott Singer invited a group of friends to go to Natchez, Mississippi (her birthplace). He went all out,” Sandra Stilwell Youngquist wrote in an email.

“It started out with all of us being invited. He would take care of all of the arrangements, accommodations, etc. All we needed to do was get there. Once we confirmed our attendance, a lovely hard-covered book arrived with all of the plantations, history of Natchez, etc. It was to give us a sneak preview of what was ahead.  

“He totally took over two bed and breakfast inns and brought in special chefs, etc. … We met for cocktails and dinner. The whole weekend was amazing, including going to plantation houses for dinners and lunches. We were surprised by going to the first plantation church and we were met with an entire choir singing to us. …  

“Retta was Little Miss Natchez when she was about 6 years old. Elliott found the regular Miss Natchez (who was about 17 years old when Retta was 6). He had her come and meet up with all of us, and the mayor of Natchez joined us. He had a banjo player onboard the bus. There were lots of photos, food, wine, laughter and fun. Then, on top of it, he hired The Temptations to play one night. Retta loves Motown music. 

“We’ve co-hosted wine dinners together, traveled to Europe, California twice, New York several times and the Bahamas, etc.,” Stilwell Youngquist wrote. “However, this took the cake!”


In general, parties have grown a bit, well, demure in the past decade or so, said the party aficionados who were polled.

“Whereas I used to see caviar and escargot and champagne, I really do now see cheese and crackers,” Davis says. “But I think what’s really important for any gathering is the people. If they’re fun and nice and having a great time mixing and mingling and enjoying each other’s company, it doesn’t matter what people are wearing or what alcohol is served.”

And after all, people yet to be seen at galas this season include Mike Huckabee, Lesley Stahl, Jeb Bush, Newt Gingrich, and former POWs Capt. Wayne Smith and PFC Jessica Lynch—and plenty of amusing and generous residents of Southwest Florida.


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