The Silver Traveler

Cuba: Tricky, Soulful, and Entirely Worth It

In the early 50’s my grandfather would fly to Havana regularly for business (He was a food broker) and he imparted his love of the country and its people to us.  He had a coffee roaster in his home to roast the Cuban coffee beans and of course he had the best cigars and pipe Tabacco.

Going to Cuba can be a little tricky, but the effort pays off in ways you can’t imagine. After visiting several times—First with our family and then by cruise ship—we will go back as often as we can.  The mix of the old, very old, and the new, the architecture, the evolution of their politics and how the U.S.A., Russia, and China have affected their economy through the eyes of the Cuban people is fascinating. 

A Home Away from Home

For our longest stay, we used two Airbnb ‘s.  The first was a retired couple who shared their home with us. It was as authentic as it gets—we even slept in their personal bedrooms!  The second AirBnB was an old mansion type home divided into a duplex.  The top floor was used for room rentals and the family’s private space was on the bottom floor. (Addresses of the accommodations are on my sample itinerary to download)

• A Familiar Sight: We walked in to find our host watching a Seattle Mariners game!
• Morning Rituals: Both places made us a fresh Cuban breakfast every morning.  The retired couple served us at his kitchen table.  The second AirBnB actually had maids to cook our breakfast or any other meals we wanted and made up our rooms every day.  Our meals were served on a large balcony were we could sit and relax and view the neighborhood.
• The Connection: Their daughter, who lives in San Francisco, helped us navigate Havana and pack exactly what we needed.  She also introduced us to her friend Joel, a taxi driver, who took care of all our tour and travel needs.
• What to bring: Everything you think you might need. Particularly hygiene, first aid,

The Art of the “Unusual” Gift

Because things can be hard to find in Cuba, we brought some specific gifts for our hosts:

• For the First Host: A 50amp motor controller for a water pump he couldn’t find parts for.
• For the Second Host: Candy and tchotchkes from our home in Washington State.

Walking the Streets of Havana

We spent about eight hours a day exploring on foot. Havana is incredibly walkable and is perhaps the safest country we have ever been in for walking everywhere.

• A Different Reality: We were stopped at the puntos de control (checkpoints) operated by the police as we headed out of Havana to the beaches and cigar farms.  Cuban citizens cannot move internally through the country as freely as we do in ours and are stopped to ensure they have proper IDs and vehicle papers.

Religion and Race

We found the diversity of religions and the acceptance of those religions refreshing.  My husband visited a mosque, we had coffee with Santeria followers and stood outside the synagogue and catholic church. 

We are an interracial family.  We travel widely and, in our travels, have (unfortunately) become accustomed to being noticed.  In Cuba we absolutely blended in.  Our American clothing labels, and our language were giveaways at times that we were not Cuban.

The “Can’t-Miss” Highlights

If you’re building your own Cuban itinerary, these were the moments that defined our trip: (download our itinerary excerpt)

Activity	Why We Loved It
Lithograph Class	Taken from a renowned artist in his personal studio.
Rooftop Salsa	Learning to dance on an apartment rooftop under the sun.
1950’s Cars	Hiring classic cars and drivers to take us to the beach for the day.
Tabacco Farm	Buying cigars directly from a farmer on his land.
Colon Cemetery	Walking through a cemetery
Cigar Factory	Watching women hand roll cigars
Rum	Cuban rum (and coke) in Cuba
Beaches	Santa Maria del Mar and Veneciana (skip Maria-too crowded)
Ventanitas	Roadside coffee and sandwich stands, Cubano sandwiches
Jazz Club	Great jazz artists at the Fox and the Crow Jazz club
Malecon	Walking the malecon
	AND SO MUCH MORE

  A Few Parting Tips

• Cash is King: You cannot use U.S. credit cards here. Bring plenty of cash; we found USD and Euros have the best exchange rates.
• Bring Your Curiosity: Each trip has left us more fascinated by the culture, politics, and the beautiful flora and fauna.
• Itinerary Excerpt:  Download it here as a pdf file.

Required Documentation:

U.S. citizens traveling to Cuba must have a valid passport (with 6+ months validity), a Cuban Tourist Card/Visa, mandatory travel medical insurance (often included in airline tickets), a D’VIAJEROS electronic entry form (submitted within 72 hours of travel), and must fall under one of 12 authorized OFAC travel categories. 

Key Documentation and Requirements:

• Passport: Must be valid for at least six months beyond your arrival date.
• Tourist Card/Visa (Pink Card): Required for all travelers, typically purchased through your airline ($85–$100) or travel agency. This is not the green card used for non-US travel.
• Authorized Travel Category (OFAC License): Tourism is prohibited. You must choose one of 12 allowed categories, such as “Support for the Cuban People”.
• D’VIAJEROS Form: An electronic arrival/departure form that generates a QR code, mandatory for entry.
• Medical Insurance: Cuban health insurance is required, often added to airline ticket costs ($25).
• Proof of Return: A return or onward ticket is required for entry. 

Important Tips for U.S. Citizens:

• Document Retention: Keep all documentation related to your travel category (receipts, itinerary) for five years, as required by OFAC.
• Currency: U.S. credit/debit cards often do not work; bring cash (USD or Euros) to exchange.
• Cuba Ready Booth: If flying from Miami, use the ‘Cuba Ready’ booth to verify documents.
• Cuban-Born Travelers: Special visa requirements or a Cuban passport may be required.