Vision beyond the horizon helps Chicago's First Lady Cruises grow, succeed
Holly Agra tilts her head upward, letting sunlight settle on her face.

She stills her fingers from fiddling with her iPhone. She gazes at the bridges and the current of the river, relishing the vista from the deck of Chicago's Leading Lady, the biggest boat in her company's fleet.

Agra glances at the vast Montgomery Ward building, which now houses Groupon and contains the desks of thousands of employees. She contemplates her own outdoor workplace and its riverside scenery.

"Aren't we lucky we're outside?" she said. "And they're all inside?"

Chicago's First Lady Cruises has been the official fleet of the Chicago Architecture Foundation River Cruise for 19 years and is the sister company of Mercury, Chicago's Skyline Cruiseline. Agra, 54, has been at the helm of growth at both since she smashed a bottle of Dom Perignon on the hull of the First Lady's first ship in 1991.

A year later, she proved to be an executive with insight and guts, evident when massive flooding left her boats stranded. She didn't call or write the mayor's office to say she needed help; she sent a telegram. It worked, and the city sent the U.S. Army Corps of Engineers to assist.

The four ships of the First Lady fleet are moored at the southeast side of the DuSable Bridge at Wacker Drive and Michigan Avenue, along with the Mercury and Skyline Queen. (A smaller yacht, the Lady Grebe, is tethered at Burnham Harbor.) Warm weather prompted some early ventures this spring, and NATO diplomats kept the boats busy last week, but Memorial Day weekend marks the start of high season for the seven vessels, which took about 250,000 people up and down the Chicago River and along Lake Michigan last year.

It's a year of national and international scope for Agra, too. In her second term on the U.S. Travel and Tourism Advisory Board, she has been urging the federal government to ease visa restrictions so that tourists from countries like China and Brazil can have an easier time visiting America, and in turn, Chicago.

"She's a real champion for Chicago," said Grant DePorter, the CEO of Harry Caray's Restaurant Group, which partners with First Lady to provide catering. "She just thinks for the greater good and is really a huge visionary, and those are the things that will help keep Chicago strong and competitive."

Of Bob and boats

Boats, and the business of boats, didn't enter Agra's life until she was 19 years old. That's when she met Bob Agra.

Bob has one of those quintessential Chicago family stories, beginning when his grandfather, Arthur Agra, emigrated from Portugal to start carrying passengers around Lake Michigan in 1935. His boat, which departed from Navy Pier, carried six passengers.

In the 1950s, Arthur and his son, Robert, Bob's father, moved their boats to the southwest side of the Michigan Avenue bridge, now the DuSable Bridge, and began operating as Mercury Sightseeing Boats. By then, their vessels could carry 40 passengers.

In the next decade, they expanded their operations to the State Street bridge and upped their capacity to 200 passengers. Robert later consolidated the fleet at the Michigan Avenue site, which his son moved east in 2001.

A couple of years before Holly and Bob met, Robert died after a series of heart attacks, leaving his son in a precarious position.

"Your dad passes away when you're 18 years old, you don't go to school," Bob said. "You keep the family business going."

In 1977, Holly was studying business administration at Harper College in Palatine when, through friends, she met Bob. While running the family business full time, Bob had started taking night classes in accounting. He still remembers the restaurant where he decided he would marry her.

Aptly, the eatery was named Down the Hatch.

"She was very nice, very beautiful, and she had a lot of business sense," Bob, 54, said of meeting Holly.