If it comes as a surprise to you that the Sperry Top-Sider Charleston Race Week is one of the nation’s largest sailboat races, you are not alone.

“I race in events all over the country, and I’ve had to get up in front of the CORA (Charleston Ocean Racing Association) crowd and try to explain to them that this isn’t our little old Charleston Race Week anymore,” said Randy Draftz, who’s in his fourth year as race director. “This is like a top-drawer, best event in the country kind-of-thing nowadays. ... There might be an event in Chicago that has as many boats, but I don’t think so anymore.”

In 16 years, Charleston Race Week has grown from a handful of local sailors into a marquee regatta attracting boats from around the world, with Sperry Top-Sider as the title sponsor.

This year, 269 boats have registered, including six in the first 50-feet-and-longer category.

“We’ve ratcheted it up to another caliber level,” Draftz said. “It’s off the hook.”

By land

For landlubbers and casual sailors not competing in the four days of races this week, the event also includes plenty of shore-side action.

Most sailors have been groomed toward an affinity for the sport’s signature cocktail, the Dark ’n’ Stormy, a Bermudan-born amalgam of dark rum, ginger beer and a pinch of lime. The drinks will be poured by the dozen at the daily post-race beach parties.

Over the weekend, Draftz estimates that attendees consume 260 gallons of Gosling’s Rum — about a gallon per boat — and peel through 150 pounds of limes.

“It’s scary,” laughs Draftz. “I think it’s the widest disbursement of Gosling’s anywhere.”

The imbibing doesn’t occur on the water. Even local sailors who breezily compete in the association’s Wednesday race series step up their game for Race Week. Still, evenings at the Charleston Harbor Resort and Marina at Patriots Point allow for some serious reveling.

Tickets to the on-shore events are available via a weekend pass, which includes dinner, an open rum and beer bar, and live music each night. Thursday’s lineup features Ben Fagan and Friends, with 17 South taking the stage on Friday. There also are daily bocce and cornhole tournaments.

For people not seeking a four-day commitment, Saturday night’s beach party is available as a stand-alone ticket, with music by Calvin Taylor and the ubiquitous all-you-can-drink Gosling’s.

Saturday afternoon will be highlighted with a display of the “oldest trophy in international sport,” America’s Cup.

Tom Ehman, Golden Gate Yacht Club (they currently hold the cup)vice commodore and 32-year America’s Cup veteran, will be on hand at 1 p.m. to present a kid-friendly multimedia presentation of the historic race’s history and its latest developments.

Speaking of trophies, Race Week underwent an upgrade this year thanks to Isle of Palms-based sculptor Fred Moore, who emblazoned the trophies’ metal sails with the Sperry Top-Sider logo and the CORA flag, flying over a hand-carved wooden skiff.

“It’s a Charleston-oriented trophy that people will want to win,” Draftz said. “It’s not something they’ll just put off on a bookcase somewhere.”

By sea

For a contest with no cash prizes, the level and variety of competition are staggering. This year’s series includes six courses, including an open ocean cruising category.

Sail Magazine even got behind the event, sponsoring a Best Around the Buoys contest, won by a Florida team whose trip to Charleston is provided by the magazine and CORA.

Six foreign teams have registered, representing Sweden, the U.K., France and Bermuda. Eighty-five percent of the boats are from somewhere out of town. Nevertheless, Charleston teams often manage to beat the out-of-town entrants on their home waters.

Don Terwilliger, a local engineer, has watched Race Week grow from a small locals event into a major regatta, racing on three different boats over 11 years of competing. He won his class two years ago with the boat Dauntless, “and a whole lot of second place finishes, every other year.”

“Last year, we were racing against our friends on Big Booty (another Charleston-based team) and went out the first day and got three first place finishes out of three races,” recalls Terwilliger. “We had to go in really light winds the next day, which is not our forte with Dauntless, and watched the first place slip away from us by Sunday.”

With more boats and more categories, Terwilliger anticipates some of the tightest races ever this year, with finishes within 15 or 20 seconds of each other.

“There’s a buzz around the marina for the whole week or two leading up to the race, with the local guys tweaking their boats and everybody from out of town rolling in,” Terwilliger said. “This is our big event for the year, and we’re fortunate that we don’t have to travel to participate.”

Offshore races launch from the harbor each morning at 8 a.m., with in-harbor racing beginning at 11 a.m.

More than 350 staff and volunteers work the event, including 150 in-water staff who set buoys and carefully time and document each boat’s rounding time. Whenever the wind shifts, the whole course must be quickly reset.

“These guys are super busy all day long,” Draftz said, adding that the Coast Guard is on hand to help keep the race courses clear of other boat traffic.

Still, spectators with their own boats are welcome to watch the action from the water.

“You can get pretty close and get a good idea of what’s going on,” Draftz said.

To view the races from land, organizers suggest watching from the regatta village at Patriots Point or from Demetre (Sunrise) Park on James Island.