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Cuba Travel History


Legal travel to Cuba was long a dream of American travelers, who were prohibited from visiting the island since travel restrictions were imposed in 1963. Policy changes in 1999 opened the door for any American to legally travel to Cuba with insightCuba under authority of the U.S. Department of Treasury, Office of Foreign Assets Control. 

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

Since our humble beginnings, we’ve sent tens of thousands of travelers to Cuba, have been featured in hundreds of major news outlets including The New York Times, CNN, NBC, Conde Nast Traveler, Travel + Leisure, USA Today, Fox News, and more. We offer a host of Cuba Tours, Personalized Tours, and Cuba Cruises with hundreds of departures each year

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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.

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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.

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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.

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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.

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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.

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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.

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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.

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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.

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On January 28, people-to-people 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.

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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. 

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

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InsightCuba receives authorization from the U.S. Department of the Treasury to offer an ocean cruise around Cuba, and the first authorized cruise for Americans since 1963.

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

December 17, President Obama announces efforts to normalize relations with Cuba. 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 U.S.-Cuba relations and travel to the island nation.


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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. By year's end, Cuba was ranked the hottest destination for U.S. travelers by various travel publications.

Cuban Embassy in Washington, DC opens and insightCuba is present for the opening ceremony.

insightCuba's president, Tom Popper, meets Cuban President, Raul Castro during his historic visit to New York and the United Nations

U.S. mobile phone carriers began roaming service in Cuba.  

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insightCuba launches its new brand, Masala Expeditions,bringing its acclaimed people-to-people tours around the world. 

Condé Nast Traveler names insightCuba the worlds top Cuba Travel Specialist.

People-to-people travel for individual U.S. citizens is authorized. President Obama travels to Cuba, marking the first time an American President has visit Cuba since Calvin Coolidge in 1928. 

Carnival Cruise’s, Adonia, is the first large U.S. commercial cruise ship to dock in Cuba in more than 40 years. 

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Condé Nast Traveler names insightCuba the world's top Cuba Travel Specialist for third straight year. 

President Donald Trump repeals people-to-people travel for individual U.S. citizens, which President Obama authorized the year before. However, the White House leaves many of the Obama travel provisions which increased U.S. travel to the island, intact. 

insightCuba and acclaimed world music record label, Putumayo World Music collaborate on a series of tours to Cuba and beyond. 

Cuba's first luxury 5-star hotel, the Gran Manzanas Kempinski opens in Havana. 

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Condé Nast Traveler names insightCuba the world's top Cuba Travel Specialist for fourth consecutive year. 

Cuba achieves record breaking 4.75 million travelers. Two leading markets are Canada and the United States. 

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Condé Nast Traveler names insightCuba the world's top Cuba Travel Specialist for fifth consecutive year. 

June – White House amends Cuba travel regulations prohibiting cruise ships originating from the United States to sail to Cuba. Administration also consolidates People to People and Support for the Cuban People, the two most popular travel categories, into Support for the Cuban People. Any American can still legally travel to Cuba under this category. 

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