With its enviable tropical and coastal location, including multiple inlets connecting inland waterways with the Gulf of Mexico and beyond, Naples offers yearlong access to a big blue sea of opportunity. Boating and sailing are popular pastimes in Florida. According to the Florida Fish and Wildlife Conservation Commission, the state boasts the highest number—more than a million—of registered recreational boating vessels in the country.
Opportunities for global travel and exploration are numerous when you possess a boat. And the bigger and more self-contained, the farther and longer you can sail. Built purely for pleasure, a yacht represents the pinnacle of maritime luxury. Constructed at ever-greater lengths, privately owned luxury yachts increase in number every year. Membership in sailing and boat clubs is also growing. In addition to providing a place to dock vessels large and small, these clubs often offer a plethora of social activities and a heavy dose of fun.
The love of boating and water inspires aficionados to join sailing or yacht clubs. In 1964, because of his affinity for sailing, Jack Messmer founded the Naples Sailing Club. A handful of members raised enough money to purchase 400 feet of waterfront property on Beaumaris Island—where the Gordon River empties into Naples Bay. Eventually a clubhouse for social activities was built on-site, and in 1971, the growing club was admitted to the Florida Council of Yacht Clubs, when it officially changed its name to the Naples Sailing & Yacht Club (NSYC). In 2005, a grand new building was erected.
Women at the Wheel
In the context of a yacht club’s executive team, the bridge—a nautical term borrowed from the command structure of a ship—refers to a voluntary leadership team that guides a club’s activities and operations. Sixty years ago, a registered voting membership at NSYC was assigned to only the husband’s name when a couple joined; women served on the board in the roles of secretary or treasurer and were traditionally the ones who organized social activities and trips.
Nowadays, women are taking the helm, parlaying career-related skills or those acquired as passengers on many an excursion to roles as captains and commodores. In 2014, the first female was appointed to the highest-ranking position of commodore at NSYC. Ten years later, the club’s second female commodore, Carol Joseph, was chosen, representing a quiet undercurrent of change surfacing within the sailing world.
A commodore’s role is similar to that of a company’s CEO. Overseeing all club activities, the commodore presides over meetings and represents the club officially. Each commodore brings a specific set of skills and talents to their role. Joseph, who earned an MBA from the University of Illinois Chicago, spent years working in the corporate world. In 1998, she partnered with her husband, Tom, to operate a small manufacturing company, Magnum Products, growing it into a successful business. In 2011, they sold the company and retired to begin a life split between Oshkosh, Wisconsin, and Naples.
Joseph is serving the first of a two-year term as commodore at NSYC. “It is my role to ensure the board maintains its focus on proper governance and financial and risk management oversight, while ensuring an atmosphere for board members to feel they have made a difference as they give their time and talents,” she says. Although Joseph states financial acumen and understanding of governance are important in her role as commodore, in her experience, “the most critical skill is being able to lead in a collaborative and supportive manner and to respect everyone on the team.”
Where Friendship Meets the Water
Joseph relays that she has always had a boat in her life and even learned how to water ski at age 5. Boat ownership for the Josephs has included a 47-foot Sea Ray, a 56-foot Princess, a 59-foot Sea Ray, and a 60-foot Hatteras. And, after stricken with what Joseph calls “foot envy”—not uncommon among boat owners—she reports they now own a 100-foot Hatteras with a full-time captain and crew, who take care of the boat as it moves between Nassau, Bahamas, in the winter months and Newport, Rhode Island, in the summer months. The Josephs also own fishing and ski boats, as well as a pontoon boat. Because they were missing the camaraderie of club cruises, they will soon add a 56-foot Princess to their fleet, which they will dock at NSYC. “True friendships are made on the water,” believes Joseph, who never thought her life would be so connected to the seas. “We have found it to be our getaway and would be hard-pressed to give it up.”
The Josephs initially joined NSYC because they needed a place to park their boat. They had such a great experience as members and met so many new friends, it helped anchor their seasonal move south, with Joseph claiming, “Boating truly changed my life.” While at sea, Joseph admits life is simpler; days revolve around reading, sunbathing, fishing, watching the rising and setting sun, and just being in nature. “It’s a fun life—a dream I would never have thought possible,” Joseph relates.
When Mary Claire Moser first floated into Naples—sitting on the bow of her boat—she remembers saying to herself, “I think I could like it here.” She and her husband, Gary, have been seasonal residents since 2001 and are members at NSYC. They own a “58-foot President, a cockpit motor yacht,” details Moser.
The Mosers spend much of the year on the water. Last summer, it was seven weeks in the Bahamas. During season, they try to go on a cruise—typically one week in length—with club members (and their respective boats) every month. “At a certain stage in life, boating becomes a passion or a hobby rather than a sport,” says Moser.
Through the years, boaters have held on to some strong beliefs and superstitions, mostly because of the unpredictability of the sea. With the advent of technology, many of those traditions have faded. However, the christening of a new boat, marking the launch and start of that vessel’s safe journey at sea, is one that continues.
It was purely by chance that Moser fell into the role of chair of boat christening at NSYC. She happened to have a copy of a prayer—from years ago when she was on a cruise where a boat was christened—in her possession. New boat owners at the club wanted to honor this tradition for their boats, and Moser volunteered. Fellow members gather, and Moser reads a few lines from the bible of boating: Chapman Piloting & Seamanship. She then recites the prayer and ends by breaking a bottle of Champagne against the hull. “It is a fun and frivolous ceremony to celebrate with friends,” says Moser, “dating back thousands of years.”
Mary Lottes serves as social chair at NSYC, where a diverse membership means people come together from various backgrounds. Lottes and her husband, Art, have been members since 2008. They dock their 42-foot Tiara Coronet in the yacht basin at NSYC. Lottes describes her duties as coordinating parties, developing themes, and figuring out the decor for each. “It is fun to have members get involved and host the parties, which help them meet one another and bond,” she says.
For those who desire more boating-related activities, the club offers plenty, including regattas and weeklong cruises during season to places such as Boca Grande, Sarasota, Longboat Key, and Useppa Island. Every year the club boats parade through local waters for the annual fleet review, a ceremonial procession with the commodore presiding.
“Joining a club transcends mere yacht anchorage, evolving into a dynamic community hub where luxury sailing, cruising, exclusive dining, and global exploration blend to foster connections, friendships, and a lifestyle of unforgettable adventures on and off the water,” explains NSYC’s director of membership and marketing, Brittany Gregg.
In a Netflix documentary of his career titled Off the Record, well-known music producer David Foster said, “In 10 years, I don’t want to be working anymore; I want to be on a boat somewhere, lying in the sun.” He shares a sentiment many people dream of—floating on a glassy sea, surrounded by blue sky and rays of sunshine. For those who partake of the yachting life, the blissful activity is a fulfilling way to satisfy a waterlust.
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