History of People-to-People Travel


Legal travel to Cuba was long a dream of American travelers, who were prohibited from visiting the island since travel restrictions were impossed in 1963. Policy changes in 1999 opened the door to legal travel to Cuba for Americans through people-to-people exchange programs, with the goal of enhancing cross-cultural relations between Americans and Cubans.

In 2000, insightCuba received its specific license from the U.S. Treasury Department’s Office of Foreign Assets Control, and pioneered some of the first Americans to legally travel to Cuba through its people-to-people programs.

When new travel restrictions were enforced in 2003, banning virtually all Americans once again from visiting Cuba, we remained hopeful that travel to the island would eventually resume. On January 28, 2011, and after an eight year hiatus, people-to-people travel was restored, meaning any American could once again travel to Cuba legally with insightCuba.  

InsightCuba guests were the first to return in 2011 on our Inaugural Trips– a feat that attracted an unprecedented whirlwind of press from CNN, NBC, Reuters, Associated Press, and more than 200 other media outlets.  For details, listen to an interview with Arthur Frommer and insightCuba’s President, Tom Popper, or watch Peter Greenbergs televised report on his trip with insightCuba.

Since our humble beginnings, we’ve sent over 10,000 travelers to Cuba, and currently offer six Signature Cuba tours, a handful of Specialty Cuba tours, as well as our acclaimed Group Travel tours with over 150 scheduled departures throughout the year. We’ve remained steadfast in our commitment to creating unique access to people and places the average tourist rarely sees. 

  • 1999

    Forty years after the Cuban Revolution, the Clinton administration announces measures to increase people-to-people exchanges between Americans and Cubans. InsightCuba, a division of Cross-Cultural Solutions, sends in its first license application to the U.S. Department of the Treasury's, Office of Foreign Assets Control, wanting to help Americans travel to Cuba legally and to build close relationships with the Cuban people.

  • 2000

    InsightCuba is granted a two-year specific license from the U.S. Department of the Treasury's, Office of Foreign Assets Control, authorizing legal, licensed people-to-people travel to Cuba. InsightCuba is the first organization to take Americans on people-to-people Cuba tours.

  • 2001

    Inspired by Cuba’s infectious rhythm and vibrant art scene, insightCuba launches a themed Cuban Music program, offering participants the chance to immerse themselves in Cuban music, dance, art and the people behind it all.

  • 2002

    InsightCuba is issued a second license authorizing legal, licensed people-to-people travel to Cuba. Shortly after, a partnership between JazzTimes magazine and insightCuba brings hundreds of Americans to the Havana International Jazz Festival. The pulsating, Latin experience draws big names in global jazz. Past performers include Dizzy Gillespie, Charlie Haden, Max Roach and Chucho Valdés.

  • 2003

    InsightCuba is issued a third license authorizing people-to-people travel to Cuba. By year's end, insightCuba is featured in over 120 nationwide news outlets, including New York Times, Los Angeles Times and Newsweek. With established on-island ties and carefully fostered relationships, the organization sent over 3,000 Americans to Cuba since travel restrictions were loosened in 1999. Under the Bush administration, the regulations governing travel to Cuba are tightened, and all people-to-people educational travel programs are suspended at the end of the year. The last groups of Americans traveling to Cuba legally under the people-to-people license return home with insightCuba on December 31, 2003.

  • 2004

    InsightCuba receives the Hospitality, Sales and Marketing Association International (HSMAI) Adrian Award for its efforts in the travel and hospitality industry. Considered the benchmark for the industry, this is the most prestigious travel marketing competition globally.

  • 2004-2010

    InsightCuba continues to strengthen partnerships and friendships in Cuba while travel programs are suspended by the Office of Foreign Assets Control. Hope remains steadfast that travel to Cuba will soon resume.

  • 2010

    In August, insightCuba receives word that the loosening of travel regulations to Cuba is pending. Preparations begin immediately to relaunch insightCuba, and resume its Cuba tours in anticipation of the restoration of people-to-people travel by the Obama administration.

  • 2011

    On January 28, people-to-people educational travel to Cuba is restored by President Obama (press statement). InsightCuba submits its license application that very same day. On June 28, insightCuba is granted its fourth license authorizing, licensed people-to-people travel to Cuba. On August 11, insightCuba is the first organization in eight years to send Americans to Cuba legally under the new people-to-people regulations, and relaunches with six signature Cuba tours.

  • 2012

    In April, insightCuba sends its 6,000th American to Cuba legally.

    On September 28th insightCuba receives its fifth people-to-people license to legally send Americans to Cuba. 

  • 2013

    On June 30, insightCuba receives its sixth people-to-people license and launches its new Vintage Cuba tour.

  • 2014


    InsightCuba receives authorization from the Office of Foreign Assets Control to offer its new tour, Cuba by Land & Sea, which will be part land tour and ocean cruise around Cuba.  Details to be released soon.


    InsightCuba receives what it believes to be the first amateur sports license allowing Americans to participate in the Marabana Havana Marathon. Only 156 runners are allowed to go.


    On Wednesday, December 17, President Obama announces efforts to normalize relations with the Cuban government. The first such overture since 1959, these efforts are to include establishing diplomatic relations with Cuba, establishing banking relations between the US and Cuba, and facilitating an expansion of travel under general licenses for the 12 existing categories of travel to Cuba authorized by law. While the US Embargo Against Cuba and the ensuing travel restrictions remain in place, the announcement represents a new era in US-Cuba relations and travel to the island nation.

  • 2015

    InsightCuba celebrates its 15th year of providing licensed travel to Cuba for Americans.

    On January 16, new travel regulations are issued to make it easier for Americans to travel to Cuba, namely on people-to-people tours.