The road to the America's Cup regatta that begins this fall in Auckland, New Zealand, has been long and rocky. With a 4 1/2-year wait since Team New Zealand swept yachting's grand prize in five straight races off San Diego in 1995, syndicates from Japan to France to Australia to Hawaii have struggled to raise money and keep their focus.

None has worked harder than the New York Yacht Club's Young America campaign, which may have the most at stake. NYYC is the storied player in Cup history, having held the silver ewer 132 years before losing it in the summer of 1983, when Dennis Conner lost to Australia II at the helm of a boat called Freedom in an event he accurately dubbed, "The Yacht Race of the Century."

Ever since, New York has wanted the Cup back, and for only the second time in 16 years it has a chance. Its two new Cup boats are under construction in secrecy in Rhode Island, to be shipped later this summer to Auckland for two months of testing and development. After that they square off against nine other challengers in October, with the winner earning the right to sail Team New Zealand for the Cup in a best-of-nine series in February.

Five of the 10 challengers are from the United States but all the others are from the West Coast, three from California and one from Hawaii. Only the New York Yacht Club wants to bring the Cup back to Newport, R.I., where folks named Vanderbilt and Lipton and Ted Turner battled for it since the glory days of the 1930s. It's an auspicious quest that will cost millions -- and not for the faint of heart.

Suitably, the man directing New York's campaign is a formidable Cup figure himself. Young America President John Marhall trimmed the mainsail for Conner when he lost in 1983; he was boat design chief for Conner four years later when the Californian reclaimed the trophy for his home San Diego Yacht Club in wild winds off West Australia in a boat called Stars & Stripes. And it was Marshall's boat, the first Young America, Conner drove when the Cup was lost once more nearly five years ago.

Marshall is back, aiming high in a high-stakes game he's been playing for more than two decades. For the last four years he's been dodging a minefield of troubles, raising money in a sometimes hostile climate, assembling sailors, overseeing scientists and yacht designers in a bid to build a boat and team fast enough to beat the best in the world.

Now, at last, says his skipper, Ed Baird, with an exaggerated sigh of relief, "In a few more weeks we're getting our Cup boats. It's actually going to happen!"

Baird and Marshall, along with four Cup crewmates, were in Annapolis earlier this month for a stop on the long tour they've taken to the main event. They signed up to help longtime Chesapeake-based ocean racer Al Van Metre of Northern Virginia race in the 473-mile Annapolis-Newport Race.

While it was a valued chance for the Young Americans to sail a big, fast, state-of-the-art race boat, Van Metre's chartered 60-footer Rima, against good competition in a grand-prix event, it also was an opportunity to schmooze, something Marshall has been doing a lot of lately.

With more than $11 million yet to raise in his posted $40 million Cup budget, the ex-sailmaker from Addison, Maine, is working on wealthy friends in the sailing community. Van Metre is one of 64 he claims to have signed up in the Young America "afterguard club," which includes anyone willing to pony $100,000 or more to the NYYC Cup cause.

It's a strategy that sounded farfetched when hatched several years ago, as the America's Cup increasingly has become an event tilted toward big-name corporate sponsors with deep pockets. But major disappointments on the corporate fund-raising front, coupled with the booming stock market, pushed individual donors to the front in the Young America strategy and kept Marshall busy.

"He's a boat-design freak," said Baird, "but he's been working so hard raising money, he's only been down to see the boats under construction once, which is pretty amazing to me."

What convinced Van Metre to give to a Cup campaign for the first time? "The same thing that convinced me to buy all those sails from him," laughed the Virginia real estate developer, who campaigned the famous 60-footer Running Tide on the ocean racing circuit for years. "John is a very good salesman."

Marshall has had to navigate around some major financial perils. Last winter, he finally landed a multimillion-dollar corporate sponsorship from Fox Sports, then had to relinquish it when ESPN, the network that televises the Cup, threatened to withdraw if Fox remained as principal sponsor of a key competitor.

Rumors swirled that Young America was on the financial ropes, in danger of folding. Today, Marshall's answer to any who question his team's viability is: "How would you like to be looking down the barrels of two new Bruce Farr boats when the trials open this fall?"

Indeed, designer Farr, the Annapolis-based wizard whose yachts have dominated international big-boat racing the past 20 years, is a formidable weapon for Young America, even though Farr's office has yet to design a Cup winner in four tries.

Marshall also has assembled top sailors to spur the boats around the course, including skipper Baird, uniquely qualified to sail against the New Zealanders. In 1995, when the Kiwis won the trophy, Baird was on the New Zealand team, skippering the backup race boat in months of testing and practice against the one that wound up beating all comers. He knows the opposition.

Along with Baird, who steered Rima much of the way to Newport, Marshall last week brought along Young America crew boss Kimo Worthington, bowman Jerry Kirby and headsail trimmer Ross Halcrow. All are veterans of past America's Cups and all are Whitbread 'Round-the-World veterans. Consummate professionals, they got Rima's sails up and down without any drama.

While the Whitbread is a race of physical extremes, with gales, icebergs and weeks at sea, the America's Cup is not. Hardships aren't physical. Even if the wind kicks up, you get to go home to a warm bed every night.

But the financial and psychological pressures of the 4 1/2-month-long competition for yachting's top prize are as fierce as anything the Whitbread offers. So much pride, prestige and money is on the line.

When Marshall and Conner recaptured the Cup in Australia in 1987, they chose as a theme each time Stars & Stripes left the dock for the wild and windswept Indian Ocean the song "Danger Zone," from the movie "Top Gun."

It's another sort of danger Young America sails into now. They won't face big winds in Auckland, where races will be in more moderate breeze, but there's no way to avoid the debilitating perils of a slow boat or dwindling finances.

How will Young America do? It's too soon to say, given the fact none of the 15 or 16 new boats being built for this Cup season is fully up and running. Young America has Farr's expertise and a crew of top sailors, but only time will tell who got the boat-design equation right. Meantime, Marshall has weathered storms to get this far and confidently awaits the next.

Strong headwinds bashed Rima for six hours on the way to Newport, sending spray flying and sailors reeling. But the foul winds eventually abated and by the final evening, as the swift 60-footer headed for the finish in record time, the sky was a canvas of high, fair-weather clouds painted pink by the setting sun. Marshall took a perch on the windward rail and absorbed the view.

Newport, he said, would be a fine place to hold the America's Cup.

CAPTION: Young America President John Marshall, right, here with bowman Jerry Kirby, is trying to bring the America's Cup back to the New York Yacht Club.