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Cuba Trips – Connecting Cultures

Support for the Cuban People

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Minimum 3 days
Availability : Anytime
Add a Flight
To Cuba

Yes! You can travel to Cuba individually and support private enterprises while you learn from the Cuban people and visit so many amazing attractions.  This is the perfect way to connect with Cuba!

Customize Your Package by Adding Airfare, More Days and Activites in/or Outside Havana! Your itinerary will be based on your own interest – this is a suggested, general guideline.

Ways to meet the requirements of this Category (Support & Promote Independent Activity to Strengthen Civil Society)

  • Provide support by bringing needed contributions like toiletries, home goods, gently-worn clothing/footwear, confectionaries, souvenirs, etc.
  • Lodge at a private casa particular (B&B)
  • Use private transportation
  • Eat at private “paladares” (restaurants).
  • Visit with Cuban families to learn about their goals and to get insight into ways to help in the future (vocation training, small business, etc.).
  • Engage with locals with licenses (car readers, artists, musicians, book sellers, etc.)
  • Use a Cuban guide to explain all the important processes in Cuba (what type of licenses Cuba is providing for private businesses, how private enterprises work, and ways to support private projects).
  • Must engage in these type of activities full time (minimum of 6 hrs a day), and keep receipts and itineraries for 5 years.

Disclaimer: The information provided on this itinerary is based on industry practices and standard interpretations of OFAC rules and does not constitute legal advice. For more information call OFAC at 202-622-2480

Note: Further your knowledge by visiting cultural and historical sites to learn more about the Cuban culture (not a support activity)

Rate Includes

  • Visitor’s Visa
  • Lodging at private casa particular (B&B)
  • Breakfast at B&B (Supports private enterprise)
  • Private, Air Conditioned Transportation in Havana
  • Two-day private guide to explain and connect you to various meaningful experiences
  • Visits to cultural and historical sites
  • **TIPS for services not included**

Additional Services

  • To Add Roundtrip Airfare, Call (954) 368-0546 or email letty@lettycuba.com.


  • 20% non-refundable deposit to book tour
  • Balance is due 35 days prior to arrival date (flexible payment plan available)
  • No refunds will be issued within 35 days prior to arrival.
  • Travel Insurance is available from https://alphatravelassist.com/A1


ick up at Jose Marti Airport. Meet Letty’s Cuba driver. Exchange your dollars to Cuban CUC’s.

Panoramic view of Plaza de la Revolucion, Bosque de la Habana, Vedado, Malecon. Your guide will give you an overview of the main neighborhoods of Havana and its people.

Check in at a Bed & Breakfast, a great way to support private enterprise in Cuba. Through your stay, the owner and staff will describe the economics of life in Cuba. They will explain how they go about applying for a business visa, shopping for meals, and setting up the “casa particular business.”

Take a Panoramic tour around Morro and Cabaña in the early evening and then attend the famous Cannon Fire Ceremony at the Fort, event that happens every day since the 1700’s at 9:00 pm; be there at 8:00 pm (included).

Suggestion for dinner Area+53 in Vedado. (Not included)


Start your day of meaningful interaction by a walking tour at Parque Central, Capitolio (experts considers it one of the six palaces of major world relevance), Gran Teatro de la Habana (Alicia Alonso), a place for significant concerts and ballets. Continue along Paseo Prado towards the Habana Malecon, stopping to interact with a variety of locals. Local property traders will explain how they exchange their properties to enlarge or reduce their space, “permutas,” or how they go about selling their homes. Artists and musicians will share their work and aspirations. This will be an opportunity to share life as an American and how we take care of the same tasks in America. Learning from each other is the key!

Lunch at Sevilla’s Paladar at Obispo Boulevard. Sevilla’s will give you a look at a Paladar that is being, so far, successful in Old Havana. They keep a trio of musicians to entertain the visitors while waiting for their food. You might want to stand and dance to their rhythm! The food is delicious and you feel like you are just visiting a friend’s home. The guide will

Learn USA History in Havana through American writer Ernest Hemingway’s time in Havana. Start with El Floridita, one of his favorite Bars. Continue along Obispo Boulevard and mingle with locals and other visitors as you pass various shops and bars. Stop at La Lluvia de Oro and meet Musician Jorge Vigo Duarte, who will tell you about his composing inspirations and play one of his songs for you.

Suggests Castropol (not included). Ask for Benjamin who will give you an insight into the restaurant and his job as a host.


Visit a Cuban family at “barrio” Lawton. This unique experience will take you into a suburb of Havana where, enjoying a Cuban coffee, the owners will give you insight into their lives in Cuba. You will see a local “bodega” the small store where Cubans buy their food monthly allowances. The guide will explain the current dual currency system.

Lunch at Lawton’s “El Mirador de Acosta” Paladar. Try Letty’s favorite fried rice! This will be a great opportunity to invite the Cuban family (husband and wife if you like).

Next, meet the gregarious Rumba ladies at Plaza La Catedral. Their job is luring the visitors to take photos with them for a tip. You will also interact with the “tobacco grandmas,” and card readers. The Cathedral is majestic and, if open, you can tour the inside. Don’t leave the plaza without stopping La Bodeguita del Medio (one of Hemingway’s favorite). Suggest dinner at La Moneda Cubana (next to La Catedral).


Transfer to Jose Marti airport. (Be there 2 and ½ hours prior to your flight time).

The itinerary is subject to change.