Call it a game of speed, tactics, underwater rocks and double the number of hulls.

For the first time in its 43-year history, the Maxi Yacht Rolex Cup, which begins on Monday in Porto Cervo, Sardinia, will include up to five maxi multihulls. These fast and powerful catamarans, which measure at least 60 feet, bow to stern, can often sail faster than monohulls, but they don’t carry capsize-preventing keels.

This presents a challenge at the Maxi cup. The regatta is known for its coastal courses. These often wend past the Maddalena archipelago’s islands and submerged rocks, and, critically, through Bomb Alley.

This stretch of water, about 15 miles long, separates the archipelago from Sardinia’s north-northeast flank. When the strong northwesterly winds — called the mistrals — blow, Bomb Alley can get boisterous, which should yield exciting, if not scary, racing.

“This is an experiment, really,” said Andrew McIrvine, secretary general of the International Maxi Association, which organizes the regatta with the hosting Yacht Club Costa Smeralda. He said the decision was initiated by a member’s request.

“A lot of Maxi owners are getting a bit long in the tooth, and it will probably extend their racing life by a few years if they can race on a catamaran, rather than hanging on to the back of a Maxi,” he said.

Catamarans have two hulls to create stability, rather than a single narrow hull and a heavy keel. Critically, they generally lean over — or heel — less than a monohull, which makes it easier to move across the yacht during maneuvers. But if the sails are not adjusted to match the wind gusts, multihulls can lose their balance and capsize.

“There’s the old saying about running aground that sometimes gets applied to capsizing big multis: There’s two clubs, those who have and those that will,” said Paul Larsen, who is the race skipper of Allegra, an 84-foot catamaran. “It’s no joke.”

While the risks are real, regatta organizers were clear that they wanted to attract sophisticated racing-focused multihulls.

“There are a lot of horrible caravan multihulls,” McIrvine said, referring to cruising-oriented catamarans. “We won’t just take anything because it’s big, that’s for sure.”

Regatta organizers said that the multihulls would compete in their own class. However, weather depending, the catamarans could sail similar or separate coastal courses as the monohulls, potentially setting up passing situations with the slower-moving monohulls.

“I see the opening up to multihulls as a natural thing, a natural development of an event that has always been characterized by cutting-edge technology,” said Michael Illbruck, commodore of the Yacht Club Costa Smeralda. “This type of boat entirely fits with the Maxi world.”

Five Maxi-size catamarans initially entered the regatta, the maximum under the event’s rules, but one had a catastrophic fire and another capsized, sustaining season-ending damage.

Unless other Maxi multihulls enter the regatta at the last minute, that leaves three of the multihulls that will race, two of which will be making their racing debut on the Maxi cup’s coastal courses.

Regatta veterans describe these courses as aesthetically pleasing and tactically challenging, and regatta organizers said the islands could also modulate sailing conditions.

“The various courses around the archipelago of La Maddalena offer an area with limited waves when the prevailing mistral wind blows,” said Edoardo Recchi, the club’s secretary general and sports director. “This kind of course fits the characteristics of multihulls better.”

The archipelago’s often flat waters can make for fast sailing, but navigation can also be confined.

“The proximity to land puts real pressure into the decision-making as the consequences could be of far more importance than simply the race result,” Larsen said. “It’s challenging, thrilling and spectacular.”

This places a premium on crew choreography, especially when the mistrals howl.

“All the teams are working with big gear and very high loads, and mistakes can be very costly sailing amongst the archipelago,” said Kinley Fowler, an America’s Cup winner and the sailing team manager of Convexity², a Gunboat 68, describing the forces exerted by the big sails. “This will be exaggerated on the multihulls as we will be going faster, so it means that we will need to be thinking one or two steps ahead the whole time.”

Despite these scrawny margins, multiple teams are hoping for the mistrals.

“I’d prefer a windy regatta,” Larsen said. Of Allegra, he said, “The boat has proven itself to be strong and fast, and the crew know her well.”

Others are also confident about their boat-handling abilities.

“We have a really strong team and are not afraid to push the limits,” Fowler said. While the Maxi cup is the debut regatta for Convexity², Fowler said that the core team had sailed together for years. “Fingers crossed we get to light it up.”

While the three multihulls are fast and powerful, Lord Laidlaw’s Highland Fling 18, a new Gunboat 80, is built for speed. It should be able to sail at more than 30 knots in certain conditions.

“We are definitely on the edge of speed, loads, systems — and my helming ability,” he said, adding that helming a Maxi multihull is much different than a monohull. “Great to be learning something new at 80.”

As for racing the boat through Bomb Alley in a mistral, Lord Laidlaw, who has won his class at this regatta multiple times aboard his previous Highland Fling monohulls, was candid.

“A bit scary, if I am honest,” he said, explaining that the team had taken precautions to prevent capsizing. They include incorporating sail-handling equipment that automatically releases the ropes that control the sails if certain thresholds (loads or heel angle) are surpassed.

As for dealing with a possible capsize, the teams — and the regatta organizers — are prepared.

“We will also be wearing helmets and Kevlar vests with built-in life jackets, something we have never done before,” Lord Laidlaw said.

Recchi, of the yacht club, said safety boats would be on the racecourse. He also said the event would mitigate risk by monitoring weather forecasts and real-time reports, and by selecting courses that best match conditions.

“Additionally, in the event of a major issue, the Coast Guard is on standby with their boats to help, and a towing boat will be also on standby in Porto Cervo,” he said.

There are the submerged rocks to consider, too.

“It is very easy to ground around the northeast of Sardinia,” Lord Laidlaw said. “Many people who cut corners have regretted it.” He admitted that he had twice hit those rocks.

Unlike monohulls with fixed keels, multihulls can retract their daggerboards, which are the vertical underwater foils that enable the boats to sail a straight course. When the daggerboards are down, multihulls often draw as much water as their keelboat counterparts.

When the daggerboards are retracted, multihulls become shallow-draft vessels, which can create tactical advantages on courses that wend past islands and submerged rocks.

“The fact we can raise the boards — where keelboats can’t — might allow us to cut a few corners where there are outlying shallows,” Larsen said. “But this is a high-stakes game.”

Lord Laidlaw said raising the daggerboards on the Highland Fling 18 took seven seconds. But then you can go “sideways, maybe further into the rocks,” he said.

While all teams want a safe regatta, they also want to win.

“Let’s see how tight the racing is,” Fowler said about sailing near the rocks. “We may have to push the limits to get a jump on the competition.”

This wasn’t a one-off assessment.

“When the racing is tight,” Larsen said, “all cards are on the table.”