In the grand reception room of a storied and opulent New York City nautical club, the Florence, Italy-based watchmaker Officine Panerai kicked off its North American Circuit of the Panerai Classic Yachts Challenge season with an event to honor the non-profit Sailing Heals and Memorial Sloan-Kettering Cancer Center. The summer-long racing series, which began on May 23, is the largest international circuit of regate for classic yachts.

Sailing Heals, a philanthropic organization, backed by Panerai, creates special sailing experiences for patients by taking them on sails with professional yachtsmen and women. “At the very crux of it, we offer a day of sailing for cancer patients and their caretakers,” said Mylissa Tsai, a Sailing Heals board member and cancer survivor who is regrettably once again a cancer patient.

Over a stately spread of fine wines, cocktails and antipasti, she discussed her experience with the charity. “How often do I get to go out on a boat and get on the water and wash away all my responsibilities and sort of put life into perspective?” Ms. Tsai  asked rhetorically. “It’s a special experience.”

The launch was a casual but moneyed affair. Attendees milled about the yacht club, exploring the model ships that adorned the gilded walls, schmoozing as Duran Duran’s original "Rio" music video ran on loop overhead.  (Apparently it was  filmed on Panerai’s restored 1936 ketch, Eilean.)

“In Boston, we’ve committed to at least ten sails with Mass General [Hospital’s] Cancer Center—that’s significant! Newport, Marblehead, Nantucket…” gushed  Ms. Tsai about Sailing Heals’s 2012 calendar. “Ambitious,” The Observer noted, especially considering that Panerai fleets will compete from May through September in the Atlantic North East, British Isles and Mediterranean (see the slideshow for the full details).

“How do patients and their entourage get to these posh locations?” The Observer wanted to know.

“We personally reach out to people who have registered through our VIP guest registry form at sailingheals.org,” Ms. Tsai explained.

The Observer was fortunate enough to see what  a “VIP cancer sail” entailed. On a sunny and sweltering day this Memorial Day week, Panerai’s Michele Gallagher invited us aboard a 1938 vintage yawl called The Black Watch. It won the Panerai Classic Yachts Challenge North American Circuit in 2011.

“That’s my mortgage!” yelled one guest, marveling at the immense yacht before hopping aboard. As the vessel drifted out into New York Harbor, participants were offered Dramamine pills or wristbands to avoid seasickness. The Observer, a hearty seafarer, passed. Before we knew it, a dashing young man was passing out glasses of wine, seltzer and beer. Next, gourmet amuse-bouches including prosciutto di parma, seared yellow fin tuna, shrimp and Aberdeen Angus beef with black truffle oil were passed around. More wine was poured. Indeed, Panerai’s Sailing Heals voyages are VIP.

The Black Watch sailed past Liberty Island, Ellis Island and southwest of Governor’s Island. “The city’s skyline is so different from this perspective,” commented one voyager. For several on board, the evening marked their first sail ever.

“This is such a unique time to just meet fresh faces that have all been touched by cancer, but the focus is sailing and the beautiful views—not cancer itself,” said one woman in between sips of her beer. A widower, whose wife had recently passed away after a bout with cancer, brought his daughter, who had served as her father’s caregiver—he, too, had battled cancer. Others came solo, knowing no one else onboard, but understanding that cancer is a common denominator that does not discriminate, no matter who you are. A young social worker at Memorial Sloan-Kettering Cancer Center spoke openly about her experiences at the hospital, supporting patients and their loved ones. Angelo Merendino, who lost his wife to cancer in 2011, talked about how he launched a photography website in her memory  to detail her fight against breast cancer. It is an emotional study of their experience and the reaction of others.

As the scorching sun began to set and The Black Watch headed back to the North Cove Marina, we felt a blanket of panic about our return to reality. We weren’t alone.

“Can we go on another one?” asked one eager caregiver, a man well into his retirement years. He was told that Sailing Heals opportunities are popular and rarely happen more than once a year for individuals—but you never know. (The last time The Observer was aboard chartered sails this nice, there was a $10,000 tab!)

The Observer left in awe—not only of the marvelous views and sumptuous grub—but of how truly therapeutic a few hours  at sea can provide the right dose of escapism for someone in a constant fight for their life.

My mother once told me that I avoided joining large playgroups because I had a fear of “disappearing” into them. Apparently I was a very metaphysical child, noticing at an early age that girls who hung out together inevitably developed a sort of hive-mind mentality—dressing the same, talking the same, laughing (at me) the same.

In my recent bid to increase my social standing and ingratiate myself into a group of fancy ladies, I have resolved to hit the charity circuit. But it’s not as easy as it sounds.

The sheer number of organizations throwing fundraisers on any given night is mind-boggling, and one misstep could lead a budding socialite to donate her time, energy and money to an unfashionable cause.

As in high school, everyone wants to be part of the cool kids’ table. (Unlike high school, however, that table will now set you back $75,000.) The Frick, New Yorkers for Children, the Metropolitan Museum, City Harvest, Save Venice, The Museum of the City of New York, The Society of Memorial Sloan-Kettering Cancer Center, The New York Botanical Gardens: These are some of the more desirable charities, as famous for their glittery, star-studded fêtes as for the causes themselves, which are unquestionably, without a doubt, “the reason we’re all here.”

Luckily, you don’t need a million dollars in order to start your social career. Just a couple hundred to join a juniors group. These organizations are the training wheels for future socials: where young men and women learn how to plan the perfect party, fill tables and woo A-listers to show up and be photographed.

For advice on how to be chicly charitable, I turned to publicist R. Couri Hay, who has worked with most of the Hearst children, Lauren Bush, Harry Winston, Sloan-Kettering, Bergdorf Goodman and Bulgari. Mr. Hay suggested I start with museums: the Apollo Circle for the Met, Whitney Contemporaries, Junior Associates of MoMA. The biggest requirement to being on a junior board (league, committee, whatever), he said, wasn’t money but age.

“I’m the one you can blame for cutting the age limit down,” the sprightly PR machine said. “I started it years ago, when I was the junior committee co-chairman of American Ballet Theatre. I noticed that people were creeping in not just over 30 or 35—but over 40! When I was on the board for the Bronx Zoo event where we actually moved it into the zoo, I put my foot down. I was like ‘Forget it! Juniors are 21 and under!’”

In Mr. Hay’s ideal world, the drinking age would be the cut-off for Juniors; 35, for Associates and beyond. “But there was hell to pay for that, because everyone wanted the cheap tickets,” he recalled. Events held by junior committees are less expensive than their adult counterparts, and they tend to be less formal. Youthful, even. “I don’t want to name names, but I would look around a room at a junior event, and there were these very big figures who argued that they went out every night and didn’t want to pay big ticket prices.
“Plus, the old group always wants to mingle with the young,” he added ruefully.

The biggest tragedy, in Mr. Hay’s opinion, occurred when Anna Wintour took over the Met’s annual Costume Institute Gala in 1995 as co-chair and canceled the post-party dance the following year. Under former co-chairs Diana Vreeland and Pat Buckley, the after-party attracted a younger set, who could spare the $100 for the late-night dance. But under Anna, even buying a place in the Met’s $1,000-per-year Apollo Circle (age limit: 39) won’t guarantee you an invite to the Costume Ball. (Though you might get invited to their unofficial after-party on the roof of The Standard.)

Looking back, Ms. Wintour told The Wall Street Journal in 2011, “It was much more fashion industry before. When I became involved, I started to invite the Nicole Kidmans and the Cate Blanchetts, and then tried to bring in the worlds of politics, literature, painting and music.”

Today, at $25,000 a head and $250,000 a table, the gala brings in a lot more money than it used to. The problem is it’s all old money now. Literally.

“That was the Armageddon for the biggest junior party there ever was,” Mr. Hay said sadly, referring to Ms. Wintour’s reign at the Met. “She thought it was ‘unseemly’ to have her celebrities walk past these ‘freaks’ partying all night, but there really was this fabulous fashion on display. Young people cutting up their own clothes and creating whole new looks.” Besides, in Mr. Hay’s opinion, those “freaks” were going to be the people donating millions in a few years. “I always said today’s juniors are tomorrow’s seniors, and the museums have mostly picked up on that.”
So how does one get on a board? “You go to parties, you buy tickets and tables, and you spend money,” Mr. Hay explained, as if I were a small child. “It is charity, after all.”

Well, some of us have a hard time raising taxi money for the trip home to Brooklyn, let alone getting our nonexistent friends to pony up thousands of dollars to buy tables. But baby steps. What do junior committee members even do?

“For me, being on a board meant raising money, since raising money means raising awareness,” Mr. Hay said. Mr. Hay worked to rope in co-chairs with last names like Hearst, Rockefeller and Roosevelt.
“My job was to gather around me a circle of my friends whose names meant something,” he continued, “Because let’s face it, New York isn’t just one big club for anyone to join. People came to these events because they wanted to rub elbows with socially prominent young people; they wanted to gawk at them, dance next to them and network with them. And then if it was a great party, Emily Smith would write it up, and that would raise awareness.”

The nuances between different sorts of events became clear to me the other night. Clutching my invitation to the Spring Thaw party, thrown by the Young Members Circle of the Museum of the City of New York, I rushed uptown for what I thought would be a repeat performance of the museum’s lavish Winter Ball. The previous month, the Director’s Council (presided over by social arbiter Mark Gilbertson) held a dazzling fête at the Plaza for the same institution. I arrived at the Museum’s UES location, breathless in a flouncy Betsey Johnson cupcake dress, looking like a debutante in frosting.

When the doors opened, I was greeted by men and women in after-work attire. Some were in jeans. The open bar was serving only gin, wine and beer, and the food was limited to some nuts and candy. I felt ridiculously out of place—one of the first times in my life I might have actually overdressed.

It turns out the Young Members Circle is a totally different breed of junior philanthropy than its more exclusive brethren. Membership is $100, and events usually run about $40-$50 for nonmembers. Since most members are young professionals with full-time jobs, committee chairs are simply whoever volunteers, and most of the event planning is done via a shared Google Doc, according to current committee co-chair David Semanoff. Last year the group raised $40,000 for the museum, including membership fees. In comparison, the Winter Ball raised $445,000 in one evening.

It seemed clear that joining the Young Members Circle would not help me grasp another rung on on the social ladder. As my editor pointed out, I could become a member of the zoo and get a free t-shirt and parking passes, but that wouldn’t make me a socialite.

Still, as I stood around people of my own age and tax bracket (all of whom were down-to-earth, relaxed and fun—three strikes against them on the Social Register), I began to see the appeal in the Young Member’s Circle’s approach. There’s something refreshing about a charity group that openly courts new blood, whether or not it’s blue.

Soprano Karita Matilla

Major patrons of the Metropolitan Opera Guild donned their finest on Sunday for the seventh annual Opera News Awards in the Plaza’s ballroom.  The soirée honored some of the genre’s foremost contributors including: baritones Dmitri Hvorostovsky and Peter Mattei, sopranos Karita Mattila and Anja Silja, as well as iconic director Peter Sellars.

The likes of Enrica and Fabrizio Arengi Bentivoglio, H.R.H. Princess Madeleine of Sweden, Annaliese Soros, Mercedes Bassm, Ira Siff, Sarah and Howard Solomon, Karen and Kevin Kennedy and the venerable Ann Ziff sashayed and blew kisses at a cocktail reception, before feasting on chilled peekytoe crab and Meyer lemon salad, grilled prime beef entrecôte and fine wines.  The awards (a crystal designed by Opera News’s art director Gregory Downer and produced by Tiffany & Co.) were presented by conductor James Conlon, Sherrill Milnes, Eric Owens and composer Kaija Saariaho, and esteemed mezzo-soprano Stephanie Blythe hosted the ceremony.

During his acceptance speech, Peter Mattei comically stumbled on exactly which organization was responsible for bestowing the award on him: “I’m not good with names anymore!” he laughed. Why has he stayed so dedicated to the opera? “It’s the people who come to listen to opera at the Met. They want to be a part of the opera house. They have the same curiosity and the confidence as the city of New York! It makes you perform better,” he confided on stage.

Verdian baritone Sherrill Milnes, who presented Mr. Hvorostovsky with his award, brought gusto, impeccable articulation and a spot of comedic relief: “I can appreciate a singer with a nice head of hair,” he said poking fun at Mr. Hvorostovsky dramatic white mane. (Mr. Milnes himself is known for his full head of hair.) “I grew up listening to great recordings from the Metropolitan Opera,” commented Mr. Hvorostovsky after accepting his prize. He stressed the significance of being a part of the Met community. “I felt like all my dreams came true,” he said. “You feel a great support from everyone at the theatre from the make-up room to the chorus.”

The booming buttery voice of bass-baritone Eric Owens was another delight, as he presented avant-garde director Peter Sellars with the Distinguished Achievement award. “There is no one else in the world like Peter Sellars,” he said with chuckle. Holding back tears as he accepted his award, Mr. Sellars stated: “Can you image a life where you get to be with these people? I love these singers because they have so much beauty. I get to work with people that are truly incredible.” Mr. Sellars, a champion of modernizing opera and expanding its audience for posterity, expressed his desire to keep opera relevant and how the Guild works to promote that initiative. “Opera is going to be here and now for a long time. It’s so important that opera speaks to as many people as possible,” he said.

Ms. Silja who shined in a white pantsuit and tiered pearls with gemstones, dedicated her award in a brief statement to her grandfather (her only singing coach) and a great love of her life, Wieland Wagner (grandson of the great composer).

But perhaps the best moment of the night came from diva Karita Mattila. After receiving her crystal she proclaimed simply, “I deserved this!” Getting an award doesn’t mean you “have to be humble,” she said.

Bottom (L-R): Baritone Sherrill Milnes, baritone and 2012 winner Dmitri Hvorostovsky, baritone and 2012 winner Peter Mattei, conductor James Conlon
Top (L-R): Host for the awards Stephanie Blythe, 2012 honoree Anja Silja, H.R.H. Princess Madeleine of Sweden, 2012 winner Peter Sellars, bass-baritone Eric Owens, 2012 winner Karita Matilla

(Photos via Patrick McMullan)