Party Confidential

The gulfshore’s celebrated gala circuit is well traveled—and well covered, with big-ticket fundraisers the public face of the region’s party scene. But what happens when this same crowd goes beyond ball gowns, benefits and their best behavior? What kind of private parties are thrown for good friends, to celebrate special occasions or for no other reason than that the day ends in y? From formal dinner parties that employ "scientific" seating to militantly casual bashes in Port Royal, with warnings about some merry-making minefields along the way, here’s a look at the region’s diverse, quirky—and fun—private parties.

Thinking big, seeing small

Do the Gulfshore’s social and business titans assume laid-back alter egos when it’s time to let the good times roll? Are you kidding? Some of the parties these high-rollers throw boast the sort of tactical planning more commonly associated with military campaigns. (For one recent birthday affair, the party-throwing friend in chief deputized a formal committee of other women to carry out her marching orders.)

"Detail and execution," says builder Todd Gates of the approach he takes to gatherings at his family’s Pine Ridge manse. A true party house, the year-old residence was built to hold gatherings of up to 350 people. Gates showed the original blueprints to Wynn’s Catering and other event pros, asking them to point out trouble spots, places, say, where a hungry mob might trap a server and her cheese tray. The home has hosted several fundraisers, but Gates won’t let its rep as a party venue overshadow private good times: welcoming 100 family and friends when daughter Courtney graduated from high school last spring or seeing the home awash in Barron-Collier blue and silver for 16-year-old daughter Brittany’s homecoming party. No detail is too small for Gates to have thought of: He has mixed 300 CDs to match every conceivable party atmosphere.

For those whose life plan is "show up and see what happens," such control is intimidating, but it’s not uncommon. For certain large dinner parties, Denise Cobb employs a "scientific" seating method, combining a hostess’ good instincts with formal logic. When she arrives, each woman guest receives a card with three numbers, each corresponding with a seat; the man’s card has one number. After the first course, Mrs. Y leaves off chatting about wine futures with Mr. X and moves to the seat bearing the second number on her card; meanwhile, Mrs. Z settles beside Mr. X, where the two might discover a mutual interest in Renaissance art. For dessert, Cobb typically reunites spouses. But why have the women move? "Because the men would get lost," says Cobb.

Faux Pas No. 1

The lovebirds who always switch place cards so they can sit together. Yes, you vowed "’til death do us part," but check for the clause that exempts dinner parties.

A mighty theme

Themed parties do require more planning and are more difficult to execute, "but they’re also so much fun," says Naples hostess Suzanne Chute. One of her reliable favorites is Valentine’s Day, with flowers and linens in pinks and reds and guests brightening up in the same colors. Chute loves the research involved in staging an unfamiliar theme. For a King’s Day party, hummus, stuffed grape leaves and lamb with mint and rice made up the menu. Male guests were given crowns in honor of the Three Kings, and everyone left with gifts of gold, frankincense and myrrh.

For her own themed gathering last spring, Mary Parent and her husband, Thomas, invited nine other couples to toast the sunset with cocktails at their 1930s Old Naples home, and then carried lanterns the short distance to Palm Cottage, the city’s oldest residence, for an authentic Victorian dinner. "It was just like it would have been in the 1890s, except we had air conditioning," says Parent.

She worked with caterer A Fare Extraordinaire to make sure the turkey, stuffing and sweet potatoes were prepared in the fashion of the Kentuckians who settled Naples. (Yes, Midwesterners, Naples was settled by Southerners.) In a bold move, she seated the men at one table and the women at another. Friend Pamela Macia says the configuration turned into a great dinner party conversations, as the women talked over all the girl stuff "that men don’t want to hear."

For the 30- and 40-somethings in Parent and Macia’s set, formal dining has a special allure. That doesn’t surprise baby boomer Carol Ann May, who says the parties she threw in her mid- to late-30s were much more formal than the impromptu dinners she stages for friends today. "I can’t believe we ate that way," she says of the cream-choked Coquille St. Jacques and butter-heavy layer cakes that once dominated her dinners.

May’s trick is to choose entrées that are both simple and substantial—Beef Wellingtons, for instance—that can be prepared ahead. "People love to be cooked for," she says. Eight to 12 guests make for a party that is big enough to be lively but small enough for her to share one-on-one time with each. One of her favorite parties was a 50th anniversary celebration she threw for Neapolitans Connie and Tom Holzer. The mix of 16 people included the Holzers’ two daughters, a prized nephew and good friends from Naples. Having people who didn’t all know each other but who had their affection for them in common made for an easy, fun evening of anecdotes and stories.

Faux Pas No. 2

Hostesses whose themed menus are more authentic than appetizing. "Stewed" may be a red flag for this when used to describe the dessert course.

Something to talk about

Beyond pairing guests expertly, some hosts take other steps to get the conversational ball rolling. A popular trick is to pose a deep question for each person to answer during a later course: "What’s the best gift you ever received?" (And if you glibly riff on a new sports car, you are almost guaranteed to be followed by a heart-tugging tale that involves a puppy, a small child or a grandparent.) One guest confesses that she would rather spend an entire evening expounding on the view of the Gulf from her condo than get put on this hypothetical hot seat.

What is and isn’t proper conversational fodder? Money? Never. How you got out before the real estate bubble burst? If you don’t mind being exiled to the far reaches of the room. Scandal? Only if it’s in the rumor or indictment stages, never if there’s actual jail time involved.

Of those old bugaboos, religion and politics, the first is generally avoided, but attorney and man-about-town Joe B. Cox says fellow guests often ask him for his opinion on politics. Very few want to talk shop with him at parties, says the noted estate attorney, unless it’s a vaguely dreamy question about offshore investments they might make, preferring to keep their real issues behind the closed doors of his office. But the significant other of a physician confesses that her guy has been known to conduct medical diagnoses over dessert. In truth, she says, when talking symptoms—even graphically—he’s in his element. Making small talk about real estate? Not so much.

Faux Pas No. 3

The over-sharer whose husband has been known to sputter, "We’re not among family here" when he hears her tell all. If you wouldn’t want your worst enemy to repeat it or your mother to overhear it, don’t say it.

Good spirits

Wine aficionados abound on the party circuit, and hosts pride themselves on their skill at matching vintages to courses. That’s why the special bottle you bring to dinner probably won’t be opened that night, unless you mention ahead of time that you’d like to make it part of a toast to their gracious hospitality. When doling out the harder stuff, bartenders or hosts-turned-bartenders can find themselves playing Tom Cruise in Cocktail—and playing him badly. To combat this, many hosts offer one cocktail tied into the theme of the night—mint juleps for a Derby party or sidecars for an old-fashioned Southern feast. And although drink trends come and go, some concoctions are so perfect they’re always in style. (We’re told, for instance, that physician Jose Campoamar’s mojito is the Platonic ideal of that rum-based drink.)

When drinking, too many sips can make for all kinds of slips. "The older people are partiers," says one 30-something with a tone akin to awe. Her favorite tale of bad behavior among her elders? The normally ladylike 50-plus Neapolitan who broke into a tabletop strip tease at a posh party. (In fairness, she was in great shape.)

Faux Pas No.4

The 40-something party girl who thinks that because she doesn’t remember throwing her hosts’ crockery at her husband, no one else does.

Dressy Bessies and the anti-Palm Beach

A word to the wise: "Casual" is rarely said casually in the Gulfshore. Pam Macia says decoding the dress code for an informal soiree is much harder than finding a gala get-up. For that, she says, "You can always wear the black dress." But while casual might mean cute top and trendy shoes or dressy blouse and long skirt, in certain circles it almost never means denim or khakis. One of our correspondents learned this the hard way when she showed up for a Naples barbecue in her weekend uniform of tank top and cargo pants, only to discover an elegantly dressed hostess and a catered lunch in the formal dining room.

She might have detoured to Tammy Alexander’s house in Port Royal, where the 30-something mom’s parties are all about "how many kids can come over with their parents" to hang out and cook out. For galas, yes, she’ll pull out the gown. But for private entertaining, "I refuse to dress up," says the longtime Naples resident, who appreciates what she says has always been the town’s quieter, less pretentious party vibe. "You don’t have to pull a Palm Beach" to have fun, she says. Macia agrees on what makes the best party starter: "Getting good friends together for no particular reason. That’s what’s most special."