Chicago’s First Lady Cruises and Mercury, Chicago’s Skyline Cruiseline recently announced the transition to the fourth generation of family leadership during its 87th year of operation on Chicago’s waterways. 

Robert (Bob) Agra III, who has been with Chicago’s First Lady Cruises for 20 years, will now serve as president and chief marketing officer of the company. He will also be vice president of Mercury, Chicago’s Skyline Cruiseline. His brother, Capt. Tim Agra, will serve as vice president of Chicago’s First Lady Cruises and president of Mercury, Chicago’s Skyline Cruiseline.

“Captain Bob and I are thrilled to charge our sons with leading our fourth generation, family-owned and operated business into an exciting contemporary chapter of our legacy,” said Holly Agra, who will step down as the president of Chicago’s First Lady Cruises and assume the new role of board chair. “As a mom and business-leader, I couldn’t imagine a grander way of celebrating 87 years than by passing the torch to our sons. Bob III and Tim have greatly contributed to our growth with the addition of three-identical, custom designed and built large passenger vessels, as well as initiating new product offerings. They have invested years in their education and use their experience to expand efficiencies, increase ridership and strengthen the collaborative two-decade partnership with the Chicago Architecture Center for our popular river cruise aboard Chicago’s First Lady.”

The Family Firm Institute reports only about 30% of family businesses operate into the second generation, 12% are viable into the third generation, and only about 3% of all family businesses operate into the fourth generation or beyond.

“Multigenerational businesses are rare, and I am dedicated to further advancing our values, service and partnerships forward into the next chapter," said Bob Agra III. "I'm fortunate to have a talented crew to work with in continuing to provide the most innovative and unique must-do Chicago experiences for years to come.”

Capt. Bob Agra Jr. took the helm of Mercury, Chicago’s Skyline Cruiseline in 1976 at the age of 18 following the death of his father, Capt. Bob Agra Sr. Mercury Cruises, which began as a single speedboat operation, was founded by Portuguese immigrant Arthur Agra and his wife Myrtle in the 1930s. The company became a success as Chicago’s first sightseeing boat company. The cruises were popular among locals seeking an enjoyable, cool lakefront respite and survived a period of national economic depression, the company said.

“Our family has been lucky to witness the growth of Chicago’s downtown business district and waterfront neighborhood,” said Capt. Bob Agra Jr., who will remain in his role as lead captain and chief financial officer of both cruise lines. “Real estate developers and city officials have worked to highlight downtown waterfronts making them more accessible and enjoyable for guests. Due to their efforts, the Chicago River is now flanked with cafes, Riverwalk parkland, and a new generation of modern skyscrapers, offering a completely different perspective than during my parent’s career on the river.”

In 1991, Capt. Bob and Holly founded Mercury’s sister company Chicago’s First Lady Cruises, which has been home to the official Chicago Architecture Foundation Center River Cruise for the past 29 years. Under the direction of Bob III and Capt. Tim, the company successfully relocated from its former suburban headquarters in 2018 to a modern downtown Chicago office space conveniently located above the Chicago Riverwalk and close to the Chicago Architecture Center.

“Carrying on the legacy that my great-grandparents established on the Chicago Riverwalk is truly an honor,” said Capt. Tim Agra, Esq. “I’ve learned so much by working with my parents over the years and bringing my legal and maritime expertise into the fold. I am excited to work closely with my brother in this new capacity to ensure we set the stage to bring more experiences to a new generation of visitors.”  

The Agras and their team of 128 professionals operate a fleet of nine passenger carbon neutral vessels docked at Michigan Avenue and Wacker Drive on Chicago’s Riverwalk and cruise along the Chicago River and Lake Michigan April through November.

Chicago’s First Lady Cruises also offers private charter experiences for weddings, meetings, corporate and social events, and can accommodate groups between two to 250 passengers.