2002
Society members, Mike Feore, Jay Higginbotham and Jill Shinault, attended the first National Summit on Cuba in Washington D.C. to campaign for a continuation of ease of travel and trade.
September
The Alabama World Trade Association and Alabama Export Council passed two resolutions written by board members, Tony van Aken and Mike Lee, that called for the promotion of trade with Cuba and eventual elimination of the embargo.
2003
August
Board members Tony van Aken and Maria Mendez collaborated with Commissioner of Agriculture and Industries, Ron Sparks, to lead a delegation to Cuba and obtain contracts for roughly $10m of goods to be shipped through the port of Mobile.
2004
January

Society Mobile-La Havana hosted the Cuban poet, Raul Mesa, who delivered poetic readings of his book Solo Contra el Mar at Daphne Public Library and the University of Mobile.
The Society traveled to the Third Annual National Summit on Cuba in Florida to again stress the economic and institutional importance of a strong relationship between Havana and Mobile. Several board members including Jay Higginbotham, Maria Mendez and Jerry Pogue spoke regarding trade normalization and historical importance between Havana and Mobile.
November
The Society won “Best Booth” at the Mobile International Festival.
Despite the rising popularity and influence of the Society, the Bush administration curtailed people-to-people visits and exchange in 2004, which drastically limited the Society’s power in creating personal connections. However, Board members maintained relevance.
2006
June
Dealing with sister-city relationships between Cuba and the U.S. across the country, the First Trilateral King Conference in Kingston, Canada featured Mobile and Mike Dow as a keynote speaker. The conference was a truly historic event as U.S. citizens voiced their right to engage globally, and the international allies proved solidarity and assistance for a global dialogue.
2008
September
The Society, in collaboration with the Pan American Health Organization, World Health Organization and the Cuban Ministry of Health, contributed to the Cuban Hurricane Relief Effort by providing beds and disposable medical supplies to the island that had suffered great damage from Hurricane Gustav and Ike.
2011
April
San Francisco attempted to replace Mobile as Havana’s sister city. To maintain relevance, the Society created a symbolic cruise, where those interested in travel to Cuba paid a $25 down payment on a round trip Mobile-Cuba cruise.
The Society enhanced the collection of Cuban-related materials at the Mobile Public Library with a donation of Cuban travel guides, architectural books, DVDs, music CDs, and children’s books.
July
Pastors for Peace led a Friendship Caravan from eastern Florida to Mexico in order to aerially send goods to Cuba. Intersecting their route with Mobile, the Society and fellow Mobilians welcomed the caravan at Mt. Hebron church with dinner and support.