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Image by Kelly Sikkema


For many years, traveling to Cuba from the United States seemed like a distant dream due to travel restrictions and diplomatic complexities. However, recent changes in U.S. regulations have made it possible for Americans to embark on a legal journey to this captivating Caribbean island. In this blog post, we will explore the avenues available for traveling legally to Cuba from the United States, allowing you to discover the vibrant culture, rich history, and warm hospitality that define this unique destination.

Understanding the Legal Framework:

Before planning your trip, it's essential to familiarize yourself with the legal requirements for traveling to Cuba from the United States. In 2014, the U.S. government implemented new regulations, allowing for authorized travel to Cuba under specific categories, including educational activities, people-to-people exchanges, professional research, and support for the Cuban people. Travelers must ensure that their trip falls within one of these approved categories and comply with the necessary documentation and reporting obligations.

Choosing the Right Travel Category:

When planning your trip to Cuba, it's crucial to select the appropriate travel category that aligns with your purpose and activities on the island. Each category has specific requirements, and it's essential to understand and adhere to them. For example, educational activities may include participating in workshops, attending lectures, or engaging with local artists and scholars. People-to-people exchanges focus on cultural interactions and meaningful exchanges with the Cuban people. Professional research trips may involve collaborations with Cuban institutions or attending conferences. Determine the category that best suits your trip's objectives to ensure compliance with the regulations.

Booking Flights and Accommodations:

With the legal framework in place, booking flights and accommodations to Cuba has become more accessible. Major airlines offer direct flights from several U.S. cities to various Cuban destinations, making the journey more convenient. When selecting accommodations, consider staying in private homes, known as "casas particulares," or authorized hotels that comply with U.S. regulations. These options provide an opportunity to support local entrepreneurs and experience the warmth of Cuban hospitality.

Immersing in Cuban Culture and History:

One of the highlights of traveling to Cuba is immersing yourself in its rich culture and history. Explore the vibrant streets of Havana, a UNESCO World Heritage site, and discover the architectural marvels, colonial plazas, and colorful vintage cars that give the city its distinct charm. Engage with locals, visit art galleries, explore museums, and experience the island's vibrant music and dance scene. By interacting with the Cuban people and supporting local businesses, you'll gain a deeper understanding of the country's culture and contribute to the local economy.


Supporting the Cuban People:

Traveling legally to Cuba provides an opportunity to support the Cuban people and contribute positively to the local community. Engage in activities that directly benefit the Cuban people, such as dining at privately-owned restaurants, purchasing local handicrafts, and participating in community development initiatives. By supporting local entrepreneurs and engaging in meaningful exchanges, you'll forge connections and foster cultural understanding between the United States and Cuba.


Traveling legally to Cuba from the United States opens the doors to a world of cultural wonders, breathtaking landscapes, and unparalleled hospitality. With the proper understanding of the legal framework, selection of the appropriate travel category, and compliance with reporting requirements, Americans can embark on a transformative journey to this Caribbean gem. Immerse yourself in the vibrant culture, explore the island's rich history, and engage with the warm-hearted Cuban people. Plan your legal trip to Cuba and discover the magic that awaits in this extraordinary destination.

  • + Books
    Selected Writings, by José Martí The Cuban Revolution: Origins, Course, and Legacy. Marifeli Perez-Stable Cuba: A Global Studies Handbook, by Ted Henken Cuba: What Everyone Needs to Know, by Julia Sweig Cuba, Or the Pursuit of Freedom, by Hugh Thomas Che Guevara: A Revolutionary Life, by Jon Lee Anderson Dancing with Cuba: A Memoir of the Revolution, by Alma Guillermoprieto. Havana Before Castro: When Cuba Was a Tropical Playground, by Peter Moruzzi
  • + Non-Fiction
    Waiting for Snow in Havana, by Carlos Eire Dancing with Cuba: A Memoir of the Revolution by Alma Guillermoprieto Enchanted Air: Two Cultures, Two Wings: A Memoir by Margarita Engle
  • + Fiction
    Telex From Cuba, by Rachel Kushner Dirty Havana Trilogy, by Pedro Juan Gutiérrez The Man Who Loved Dogs, by Leonardo Padura The Kingdom of This World by Alejo Carpentier Before Night Falls by Reinaldo Arenas Cecilia Valdés or El Angel Hill by Cirilo Villaverde Biography of a Runaway Slave by Miguel Barnet
  • + Poetry
    The Whole Island – Six Decades of Cuban Poetry (A Bilingual Anthology), ed.: Mark Weiss Violet Island and Other Poems, by Reina María Rodríguez The Bridges, by Fayad Jamís Ismaelillo by Jose Marti Man-making words; selected poems of Nicolas Guillen Legacies: Selected Poems Paperback by Heberto Padilla Muerte de Narciso by José Lezama Lima Obras Escogidas of Dulce Maria Loynaz Antologia Poetica by Fina Garcia Marruz
  • + Photography and Art
    Alex Webb & Rebecca Norris Webb: Violet Isle Jose A. Figueroa: A Cuban Self-Portrait Walker Evans: Cuba Rene Burri: Cuba y Cuba Veigas-Zamora, Vives Gutierrez, Nodal, and Garzon: Memoria, Cuban Art of the 20th Century
  • + Travelogue
    Trading With the Enemy: A Yankee Travels through Castro’s Cuba, by Tom Miller The Havana Guide: Modern Architecture 1925- 1965 by Eduardo Luis Rodríguez Tropicana Nights, by Rosa Lowinger
  • + Political
    The Boys From Dolores, by Patrick Symmes Without Fidel, by Ann Louise Bardach
  • + On-line
    Harper’s Magazine October 2010: “Thirty Days as a Cuban” The Economist Special Report on Cuba – March 24, 2012: Nuestra América by José Martí
  • + Movies
    PM, 1961, by Sabá Cabrera Infante, Orlando Jiménez Leal The Twelve Chairs (Las doce sillas), 1962, by Tomás Gutiérrez Alea I Am Cuba (Soy Cuba), 1964, by Mikhail Kalatozov Death Of A Bureaucrat (La muerte de un burócrata), 1966, by Tomás Gutiérrez Alea Memories of Underdevelopment (Memorias del subdesarrollo), 1968, by Tomás Gutiérrez Alea One Way or Another (De Cierta Manera),1974, by Sara Gómez The Last Supper (La última cena), 1976, by Tomás Gutiérrez Alea Portrait of Teresa (Retrato de Teresa), 1979, by Pastor Vega Lucia, 1968, by Humberto Solas Cecilia, 1981, by Humberto Solás Se permuta, 1983, by Juan Carlos Tabío A Girlfriend for David (Una novia para David), 1985, by Orlando Rojas Vampires in Havana (Vampiros en La Habana), 1985, by Juan Padrón Too Afraid of Life or Splat (Plaff o demasiado miedo a la vida), 1988, by Juan Carlos Tabío Papeles secundarios, 1989, by Orlando Rojas The Beauty of the Alhambra (La bella del Alhambra),1989, by Enrique Pineda Barnet Alice In Wondertown (Alicia en el pueblo de maravillas), 1990, by Daniel Díaz Torres María Antonia, 1990, by Sergio Giral Fresa y chocolate, 1993, by Tomás Gutiérrez Alea, Juan Carlos Tabío Madagascar, 1994, by Fernando Pérez Guantanamera, 1995, by Tomás Gutiérrez Alea La vida es silbar, 1998, by Fernando Pérez Video de familia, 2000, by Humberto Padrón Lista de espera, 2000, by Juan Carlos Tabío Nada, 2003, by Juan Carlos Cremata Viva Cuba, 2005, by Juan Carlos Cremata Habana Blues, by Benito Zambrano Habanastation, 2011, by Ian Padrón Conducta, 2014, by Ernesto Daranas
  • + Documentary
    Unfinished Spaces by Alysa Nahmias and Benjamin Murray. Buena Vista Social Club by Wim Wenders Dance Cuba: Dreams of Flight by Cynthia Newport Maestra by Catherine Murphy The Poet of Havana by Ron Chapman Suite Havana by Fernando Perez Yank Tanks by David Schendel Horizontes by Eileen Hofer Now by Santiago Álvarez
  • + Music
    Cuban music cannot be explained. It has to be experienced. It has to be felt. The plethora of outstanding Cuban music from the late 19th century to present is too vast and diverse to list in one place. We try to give a broad stroke overview so you can experience the musical body of work of this small country and the influence it has had on music from all over the world throughout the ages. From the early origins of danceable afro-cuban rhythms to their incorporation in everything from son, guaguanco, classical and jazz, Cuban music has influenced the greatest artists, composers and arrangers throughout history including Dizzy Gillespie, Nat King Cole and Michel Legrand, to name a few. In recent decades, the evolution of Cuban rock, hip hop and even reggaeton rivals that of any other latin american country and has influenced artists from the The Roots and Tego Calderon to Jackson Browne and The Black Eyed Peas. Irakere: Misa negra Chucho Valdés and Omara Portuondo: Danza ñañiga Pablo Milanés & Silvio Rodríguez: El breve espacio en que no estás Pablo Milanes: Yolanda Silvio Rodriguez: El unicornio azul Buenavista Social Club Los Van Van: Sandunguera NG La Banda: Necesito una Amiga La Charanga Habanera: La chica mas bella Leo Brouwer: Un día de noviembre Camerata Romeu: Camerata en Guaguanco Frank Fernández: La comparsa Santiago Feliu: Ansias del alba Carlos Varela: Muros y puertas Kelvis Ochoa: A ella de duele Descemer Bueno: El carro David Torrens: El bufon y el tragico Ernan Lopez Nussa: Fin del baile Habana Abierta: Ahora si tengo la llave Gema y Pavel: Parar de fumar Orishas: A lo cubano Raul Paz: El balcon Gente de Zona: Traidora Fernando Alvarez: Se feliz Boris Larramendi: Boris Larramendi: Siempre happy

Experience Cuba



Our two week trip was a great experience. The staff was impeccable with every aspect of the journey, from arrival in Miami for the charter flight to the amazing restaurants, walking tours and music excursions. To coordinate over 150 travelers for a premium tour would have been impossible without their wealth of knowledge and attention to detail. For myself, the band, and many of our guests, the trip was one of the best experiences of our lives!



—  Director of Development, Preservation Hall Foundation, New Orleans.

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