A man holds an American flag near the U.S. Embassy in Havana on Aug. 14, 2015, when the flag was raised over the building for the first time in 54 years. (Alexandre Meneghini/Reuters)

Officials from the District, Maryland and Virginia will pile together onto a plane late this week in the name of renewing ties between the U.S. capital area and Havana.

The 41-person delegation is scheduled to become the latest in a thickening stream of U.S. politicians and business leaders to visit Cuba since President Obama announced 14 months ago that the United States would reestablish diplomatic relations with the communist nation.

Wednesday’s announcement about the trip came a day after the stakes for future trade and tourism for American cities became much clearer: The U.S. and Cuban governments announced Tuesday that 110 direct daily flights between the two countries could resume as early as the fall.

The capital-area delegation will include D.C. Mayor Muriel E. Bowser (D), Montgomery County Executive Isiah Leggett (D) and Virginia Secretary of Commerce and Trade Maurice Jones.

The three plan to meet with their counterparts, including the mayor of Havana and Cuba’s minister of foreign trade. But there also are differences between the D.C. trip and many recent U.S. delegation visits — including one by Virginia Gov. Terry McAuliffe — that focused on trying to increase trade.

On Wednesday, trip organizers and participants sought to portray the mission as the next step in a slow thaw of relations between the estranged capitals, and one in which two cities will soon have more in common as popular tourist destinations.

Brian Kenner, the District’s deputy mayor for planning and economic development, said the District would offer to share what it has learned about preserving historic sites and infrastructure under the crush of tourists.

The Greater Washington Hispanic Chamber of Commerce, which organized the trip, also stressed that there are things the District could learn from Cuba, primarily how the developing nation has maintained high education and health standards with limited financial resources.

In a news release announcing the trip, the chamber said that the delegation would include D.C. Public Schools Chancellor Kaya Henderson and that the group would visit primary and secondary schools there to learn “how literacy, graduation and retention rates . . . remain consistently high.”

For Bowser, the trip follows a trade mission to China in November, when she was accompanied by dozens of business leaders, including a handful of top donors and associates of a political action committee set up to further her political goals. Bowser’s allies subsequently shuttered the PAC under pressure for accepting unlimited donations from companies seeking to do business with the city.

As on that trip, three business leaders traveling to Cuba are tied to a combined $25,000 in donations to the pro-Bowser PAC: Scottie Irving, president of Blue Skye Construction, and a family member gave $5,000. Edwin Villegas, president of Winmar Construction gave $10,000. Carlos Perdomo’s Keystone Plus Construction also gave $10,000. Operators of the PAC said late last year that most of the money was to be returned to donors.

Construction firms and telecom companies are among those most needed to boost infrastructure in Cuba to support the increasing numbers of tourists expected in coming years, experts say.

Chamber President Angela Franco, who recently traveled to Cuba with a top Bowser administration official to prepare for the coming trip, said she was optimistic that the delegation would secure economic and cultural connections that could benefit the D.C. area.

“We are hopeful this mission will be a start to securing future economic and community benefits for the region, its residents, and its businesses,” she said in a statement.

Other elected leaders on the trip include Montgomery County Council members Roger Berliner (D-Potomac-Bethesda) and Nancy Navarro (D-Mid-County) and D.C. Council members Vincent B. Orange (D-At Large) and Jack Evans (D-Ward 2), plus Evans’s chief of staff.

In addition to Henderson and Kenner, Bowser is also traveling with Chief of Staff John Falcicchio, senior adviser Beverly L. Perry and Ana Harvey, director of the city’s small- and local business development.

The city’s cost of the District’s portion of the delegation will be about $44,000, officials said.