Intrepid Hola Cuba: A Week-Long Cuba Tour for Americans

Cuba has long been a destination that intrigues travelers with its vibrant culture, colonial architecture, rich history, and the ever-present echoes of revolution. But for U.S. travelers, visiting Cuba comes with additional considerations, as the country falls under strict travel restrictions. Enter the Hola Cuba tour by Intrepid Travel—a 9-day adventure designed to immerse travelers in Cuba’s culture while complying with U.S. travel regulations under the “Support for the Cuban People” category.

This tour takes you beyond the surface, offering a glimpse into everyday Cuban life. From the lively streets of Havana to the rolling tobacco fields of Viñales, from the historic Bay of Pigs to the cobblestone beauty of Trinidad, this journey blends cultural experiences, historic insights, and the warmth of Cuban hospitality.

For 2025, the listeners of the Amateur Traveler podcast voted to visit Cuba as the annual Amateur Traveler listener trip. Sixteen wonderful listeners and friends accompanied me on Intrepid Travel’s Hola Cuba tour.

Cobblestone Streets of Trinidad

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• Challenges in Cuba for American Travelers
  • 1. U.S. Travel Restrictions and Compliance
  • 2. Cash-Only Economy and Currency Issues
  • 3. Power Outages and Infrastructure Challenges
  • 4. Food and Supply Shortages
  • 5. Transportation Delays and Fuel Shortages
  • 6. Visa and Entry Requirements
• Accommodations for American Travelers: Casa Particulares
  • What to Expect at a Casa Particular
• The Itinerary: A Day-by-Day Breakdown
  • Day 1: Havana – Arrival
  • Day 2: Havana
    • Santería and Hamel Alley
    • Classic Car Tour
    • Walking Tour of Havana
  • Day 3: Las Terrazas and Viñales
  • Day 4: Viñales
    • Walking Tour
    • Salsa
    • Farm to Table with a View
  • Day 5: Bay of Pigs and Cienfuegos
  • Day 6: Cienfuegos and Trinidad
  • Day 7: Trinidad and the Beach
  • Day 8: Santa Clara and Havana – Che Guevara’s Legacy and Farewells
• Final Thoughts: Is the Hola Cuba Tour Worth It?

The author in Havana

Challenges in Cuba for American Travelers

Traveling to Cuba today will still come with unique challenges, especially for U.S. travelers. Here are the key issues to be aware of when planning a trip:

1. U.S. Travel Restrictions and Compliance

• U.S. citizens must follow the “Support for the Cuban People” travel category, which requires engaging in meaningful interactions with locals and avoiding government-run hotels and businesses.
• Direct commercial flights from the U.S. to Cuba are available and not as limited as I had previously heard. We ran into some issues when our flight was delayed because once you pass through security at the airport, you are not allowed to switch flights. So we saw two flights from Havana to Miami leave while our plane sat on the runway.
• Travelers must maintain an activity log to document compliance with U.S. travel regulations, as U.S. authorities can request records for up to five years. 
• Credit and debit cards issued by U.S. banks still do not work in Cuba, so travelers must bring enough cash for their entire stay. Because of this, this particular Intrepid trip includes most meals, unlike other Intrepid trips that I have taken. But you will need money for a few meals, many small tips, a trip for your guide and driver, and souvenirs.
• This tour has less flexibility because it had to be approved by the U.S. Treasury Department. All activities are listed as required.

2. Cash-Only Economy and Currency Issues

• Exchange rates fluctuate, and the “official” rate may differ drastically from street exchange rates (which are often more favorable). We saw official exchange rates at around 100 pesos per dollar, but we routinely got an exchange rate of closer to 300 pesos per dollar through the casa where we stayed or when using US dollars.
• Some businesses and casa particulares may prefer payments in foreign currency (USD or Euros). My wife and I actually never exchanged any dollars to pesos, although most of our group did exchange a small amount.

3. Power Outages and Infrastructure Challenges

• Frequent power outages remain a major issue across Cuba due to fuel shortages and an aging electrical grid, especially outside of Havana. It was not uncommon to have power outages even half the day. Most of our casa particulares had solar, a battery, and/or a generator, but I would advise bringing an external battery to charge your devices. See my packing list.
• WiFi and mobile data access are limited and unreliable. The internet may be available at parks or squares, but requires a prepaid ETECSA card, and connections can be slow or unavailable. You can purchase an ETECSA card from an ETECSA store in Havan when you arrive. Some of the casas we stayed at had WiFi which you could use without an ETECSA card… when they had power.
• Your U.S. mobile phone plan won’t have a data plan in Cuba. You can get a SIM or an eSIM ahead of time to get connectivity.

4. Food and Supply Shortages

• We had heard that Cuba is still experiencing food shortages and rationing, but we were pleasantly surprised. Since the COVID pandemic, the government has allowed more small businesses, and we found the quality and availability of food to be great.
• Imported goods are scarce, so travelers should bring essentials like sunscreen, toiletries, and any necessary medications.
• Government-run stores accept only MLC (foreign currency via bank cards). You should not and do not want to shop at a government-run store. The only issue being that it is not always clear which is run by the government, without asking your guide.

5. Transportation Delays and Fuel Shortages

• Gasoline shortages are ongoing, leading to long wait times for fuel and fewer available taxis and buses. For instance, we had a delay for an hour while we waited for the bus driver to fill up the bus on our long driving day from the Viñales Valley to Cienfuegos. He dropped us off at a golf resort to hang out.

6. Visa and Entry Requirements

• U.S. travelers must obtain a Cuban Tourist Card (Visa), which you should obtain online before your trip.
• The Cuban government requires proof of travel insurance that covers medical expenses.
• The U.S. embargo restricts post-tour stays in Cuba—Intrepid, for example, can only book one pre-tour night, not post-tour.
• Less than 48 hours before your trip, you must fill out the online Cuba D’Viajeros Travel Form. The form defaults to Spanish, but the button at the top right allows you to switch to English.

Casa Barbara in Trindad

Accommodations for American Travelers: Casa Particulares

In Cuba, casa particulares (literally “private houses”) are privately owned guesthouses or homestays that offer travelers a more authentic experience than state-run hotels. These accommodations range from basic rooms in family homes to more upscale guesthouses, often with private bathrooms, air conditioning, and home-cooked meals.

For U.S. travelers, staying in a casa particular is not just about authenticity—it’s also a requirement under U.S. travel regulations. Due to the U.S. embargo on Cuba, American travelers must adhere to the “Support for the Cuban People” travel category, which prohibits staying in Cuban government-owned hotels. Instead, staying in privately owned guesthouses ensures that money goes directly to Cuban entrepreneurs, not the government. All the stays on the tour were at casa particulares.

Breakfast at Casa Barbara in Trindad

What to Expect at a Casa Particular

1. Personalized Hospitality – Since these are family-run, you’ll get a warm welcome and insider tips on exploring the area, but you may not get an English speaking host. Only one of the four cases we stayed in had a host we could speak to in English.
2. Home-Cooked Cuban Meals – Many casas offer breakfast and dinner options, allowing you to experience traditional Cuban cuisine. All of our casas included breakfast with lots of fruit, fruit juice, coffee or tea, some breads, and usually eggs. We also ate a couple of group dinners at a casa.
3. Basic but Comfortable Accommodations – Rooms typically include a private bathroom, air conditioning, and sometimes WiFi, though power outages can occur.
4. A Glimpse into Local Life—You’ll be staying in a neighborhood rather than a tourist zone, which provides a deeper cultural experience.

The Itinerary: A Day-by-Day Breakdown

Day 1: Havana – Arrival

With our visa and our Cuba D’Viajeros Travel Form paperwork in hand, we arrived at the Havana airport. Some of the group had arrived a day early (no more than a day early was allowed), but we arrived on the official first day of the trip. The Intrepid driver met us at the airport and delivered us to our casa. Because we had a large group, we were usually split across 4-5 different cases, which made this trip a bit more challenging.

We met our hosts, checked in, and then got a recommendation from our host for a local restaurant (asking in Spanish). Our lovely host walked me to the restaurant Paladar Don Pucho, which was a couple of blocks away. I then gathered up some of my friends on the trip from two different casas.

We had some confusion over prices as we still had dollars, not pesos. When I consulted my currency conversion app, it gave me a conversion rate that was 6-8 times lower than the unofficial going rate. It is best just to ask, “Que es el cambio?” will work. Often, the waitress would show us on a calculator. Our lunch was about $13 at a sit-down restaurant with live music. Tips for musicians are recommended at $1 per person.

We explored Old Havana on our own, walking down the pedestrian Obispo street, exploring a craft market, looping around part of the Malecon, and finding a local ice cream shop. There, we bought five small cones, a soda, and a water for $4 USD and even got back some pesos in change.

PLaza de Armas

Some parts of Old Havana like the plazas or the pedestrian street are quite lovely, but many of the neighborhoods where we stayed were pretty run down with garbage on the street, buildings with peeling paint, and potholes. It was clear from the start that this tour would not convince me to become a Marxist.

The official trip started with the orientation meeting, during which I handed out tour t-shirts. We then met our great guide, Estephan, who told us about our trip. This was followed by our first group dinner (included) at a nearby restaurant. We had the option of ordering pork, chicken, beef, fish, or lobster. The food was great, but by the end of the week, we laughed that there was a great variety of food in Cuba: pork, chicken, beef, fish, or lobster.

To our surprise, on the trip most meals included 1-3 drinks, which could be water, a soda, beer, maybe wine, and typically a couple of Cuban cocktails like a mojito or a Cuba Libre. It soon became clear this was the drink your way through Cuba tour.

Day 2: Havana – Classic Cars, Afro-Cuban Culture, and Colonial Sites

Santería and Hamel Alley

Our first full day of the trip started with a ride in a classic 1950s car to Hamel Alley to learn more about the Afro-Cuban Religion Tour Santería. Santería is a religion that blends African and Catholic traditions. 

Hamel Alley in Havana is an open-air cultural space celebrating Afro-Cuban heritage and Santería through bold murals, sculptures, and live rumba performances. Created in 1990 by Salvador González Escalona, this once-neglected alley was transformed into an artistic hub filled with symbolic imagery and repurposed materials, reflecting Santería. Visitors can explore the colorful (if fading) murals, learn about Santería traditions.

Santería believes that the world was created by a god who basically then retired and left the actual running of things to spirits known as orishas. These beliefs came to Cuba with enslaved Africans. In Africa, hundreds of orishas were worshiped, but in Cuba, less than two dozen made the cut. In Cuba, each of these orichas was mapped to specific Catholic saints so that you could celebrate a saint’s day in church in the morning, and then drink rum, smoke tobacco, and dance in the afternoon to celebrate in a more African-inspired fashion.

Initiates to Santería must wear white for a year, live with a curfew for a few months, and abstain from sexual intercourse for 3 months (the initiate that we talked to said that last one is more of a guideline). One with a gift of divination will tell the initiate who their personal orisha is. Each member of a household would have their own personal altar to their orisha, whom they would consult when there was a need.

Classic Car Tour

We left Hamel Alley in a new set of five classic cars,  all convertibles.  A highlight of Havana is the classic car ride, where you cruise the streets in a well-maintained 1950s American convertible, taking in sights like Revolution Square, Parque Almendares (with tall trees and climbing kudzu), the Malecón waterfront, and the elegant mansions of Miramar. Ours was a 1952 Chevy being driven by the current owner and the grandson of the original owner. 

When I saw people doing classic car rides in Cuba, it seemed pretty touristy. It was, but it was also very fun. I had a big stupid grin on my face much of the time.

Walking Tour of Havana

We were dropped off back in Old Havana for a group lunch, as always, with live music. After lunch, our guide Estephan led us on a walking tour through Old Havana.

Plaza Vieja

We explored Old Havana’s four main squares, each offering a unique perspective on the city’s colonial history and vibrant culture. The squares we visited included:

• Plaza Vieja (Old Square) – Surrounded by colorful colonial buildings with bars and cafes.
• Plaza de San Francisco de Asís—Located near the harbor, this square features the San Francisco de Asís Basilica and some of the mansions of the colonial period nobles.
• Plaza de Armas – The oldest square in Havana, filled with gardens, home to the Palacio de los Capitanes Generales, a colonial-era fortress that now houses the Museum of the City of Havana.
• Plaza de la Catedral (Cathedral Square) – Home to Havana Cathedral, a prime example of Cuban baroque architecture.

During the tour, we learned about Havana’s history, the Spanish colonial influence, and key historic figures such as José Martí, a national hero who fought for Cuban independence, whose statue is in the Plaza de Armas. Look closely at the stone from some of the colonial buildings and you will see they were constructed of limestone. You can see fossilized coral in the stone.

Day 3: Las Terrazas and Viñales

As we drove out of Havana, we made one last stop at Fusterlandia, an art project by an artist (now 80) who said Picasso was his artistic father and Gaudi his uncle. He started by doing a mural outside his own home and went on to create murals all over his home and neighborhood.

He turned a fishing village into an art enclave. We toured his house, saw a video and then bought artwork from local artists. Throughout the trip, we had the experience of “you only want how much for that?”

Leaving Havana, our tour headed west to Las Terrazas, a UNESCO-designated biosphere reserve known for its commitment to sustainable tourism. This area was originally coffee plantations and then denuded of trees for the charcoal industry. Now, this small community showcases Cuba’s efforts in reforestation and ecotourism. We had a tour of the community, including a hotel and the gallery of a local artist and paper maker.

Lunch was at an old coffee plantation on the top of the hill with views for miles.

Our drive continued to the Valley of Viñales. We arrived in the rain, but the rain let up just as we reached a vista point above the valley, with its stunning landscapes of karst mountains and small tobacco farms. 

Dinner was a cooking demonstration and a delicious meal at Balcon del Valle. The restaurant would have had a great view of the valley had we visited when it wasn’t raining and dark. Our chef Alienka, our interceptor Estepan, and volunteer sous chef Larry showed us how to make some of the traditional dishes.

I was surprised that the cook uses a charcoal fire to prepare dishes for a restaurant full of guests.

Day 4: Viñales

Walking Tour

We took a guided hiking tour of Viñales Valley, which is a UNESCO site. I had not understood that the tour of the UNESCO site was a hike through the local small farms. Our local tour guide was particularly knowledgeable and entertaining. We saw ox-drawn plows and carts, small family farms, coffee trees, tobacco fields, yuca, and fields of vegetables for local consumption. 

This region is famous for producing Cuba’s world-renowned cigars, and we visited a family-run tobacco farm, which provided insight into traditional cigar-making methods. Every farmer who grows tobacco will dry the tobacco and then is required to sell 90% of their crop at a fixed rate to the government. They will only make something like $25-50 for their crop in this fashion. 

With the other 20% (that was the math our guide told us), they ferment it in the family’s secret ingredients and then dry it again before rolling a variety of styles of cigars. The other wrapping leaves are grown separately under cheesecloth so that they are soft and flexible. On the plant, the top leaves have the strongest flavor and the most nicotine. They pick the plan first with the lower leaves, then the middle, and then the top, keeping these leaves separate so they can purposefully use the right strength leaf for the cigar they are creating.

Am I the only one who didn’t know that you don’t inhale the smoke from a cigar? We had the chance to watch them roll a cigar, and then some of the members of our group sampled cigars. The farmers remove the stem of the leaf, which has the most nicotine, before rolling. The cigars created by the government leave in the stem and skip the fermentation step.

Cigars cost $5-9, with the stronger ones being more expensive. As an American, though, you cannot bring them home.

Salsa

We had a one-hour salsa lesson in the afternoon. There were no fans in the studio, or if there were, the power was out again. So we sweated, stepped, and smiled through a lesson with the help of a team of local dancers. 

Farm to Table with a View

We ended the day with dinner at a farm-to-table restaurant overlooking Viñales called Finca Agroecológica El Paraíso. This organic farm and restaurant is known for its spectacular views of the Viñales Valley and its commitment to sustainable agriculture. Guests enjoy fresh, locally grown ingredients, with meals featuring organic seasonal vegetables and traditional Cuban dishes. 

As we ate, we watched the sunset over the beautiful valley.

Day 5: Bay of Pigs and Cienfuegos

Day 5 was a driving day. We had to make our way from the western part of the island, back through Havana to the center of the island and Cienfuegos. We stopped in Havana to refuel our bus. Because of fuel shortages and long lines, our driver dropped us off at a golf club to wait an hour. We had lunch at a private restaurant for fast food. This was the chance to try cubano sandwiches or even hamburguesas (my advice is to wait until you get home to order a hamburger).

We also stopped at the Korimakeo cultural project that Intrepid supports. It has a school for students aged 17 up who have had difficulties at home. It offers art, music, and dance programs. We saw a dance performance, a musical performance, and an art gallery. The dance performance also included younger children from the local community.

Estephan showed us a documentary on the bus about Fidel Castro’s life, which was definitely pro-Fidel but interesting. And fittingly we made a brief stop at the Bay of Pigs for sunset, where a failed CIA-backed invasion in 1961 cemented Fidel Castro’s revolutionary rule. 

Due to our late arrival in Cienfuegos, we postponed a walking tour until the following morning and had dinner together at one of the casas in the courtyard.

Day 6: Cienfuegos and Trinidad

The next morning we toured Cienfuegos, a coastal city with French colonial architecture. A guided walking tour of the city center takes you through pastel-colored mansions, the grand Tomás Terry Theatre, and the city hall on a very attractive central plaza. Cienfuegos is a UNESCO World Heritage site.

We had an unexpected extra hour to explore the city and a bit of the waterfront when the driver noticed our bus had a flat tire. With the potholes on the main highways, it was not much of a surprise.

We drove up into the hills to a farm, where we trekked past a barbed wire fence and past a field with cows and pigs to a waterfall. Only Nonie and I jumped into the cold water, but everyone appreciated this pretty spot.

We had lunch on top of the hill at an old coffee plantation where they roasted a whole pig for our lunch. Many of the members of the group bought some coffee to take home.

We arrived late into Trinidad and put off our walking tour until the next day. However, we visited a local pottery shop called Casa Chichi, where the Santander family has been crafting ceramics for generations.

We ate dinner at a restaurant on the main plaza. Despite the communist paradise that Castro intended to create, we did run into some beggars in Cuba, including one who tried to get our attention throughout our dinner. Intrepid’s policy on this tour is that we should not give money to those who are begging but instead support the people through projects they have vetted.

Day 7: Trinidad and the Beach

Arguably Cuba’s most photogenic city, Trinidad is a UNESCO World Heritage Site known for its well-preserved Spanish colonial architecture and cobblestone streets. Our guided tour through the cobblestone streets of Trinidad stopped at three historic mansions.

The first of these mansions was Casa de La Trova, which has become a music venue.

Next was the Museum of Architecture on the Plaza Mayor, where we had a tour of what was once a state-of-the-art mansion, complete with gas lamps and a new-fangled shower.

One was the Museo Romántico, which had been refurnished with furniture as it would have been when this was a mansion for a rich sugar baron’s family in the late 1800s.

We had one last stop at a Santería shrine of Yemayá, where locals pay homage to this Afro-Cuban oricha who is held to be the water deity, the mother of all orichas, and the mother of humanity. 

After a lunch on our own, most of the group headed to the beach at Playa Ancón to enjoy the warm Caribbean waters. Here, you can rent a lounge chair for $1, sip a fresh coconut, or a cocktail for $3.

While we were enjoying the surf, a local fisherman walked up with a net full of live lobsters. A couple of the members of the group took him up on a whole lobster, cooked over a wood fire on the beach for $10.

Dinner was on the rooftop of a casa.

Day 8: Santa Clara and Havana – Che Guevara’s Legacy and Farewells

We left Trinidad and drove back to Havana. We drove through the Valley de los Ingenios, or Valley of the Sugar Mills, another UNESCO site. This area made the sugar barons rich. It was enabled by salve labor until the abolishment of slavery and then by an imported Chinese labor force. The work was hard, hot, and dangerous.

On the bus, Estephan showed us two more documentaries. One was about the quest for Cuban independence from Spain and later from the United States, and the second focused on some of Cuba’s economic difficulties. 

We stopped in Santa Clara, the city best known for its connection to Che Guevara. We made a stop at the Che Guevara Mausoleum and Museum but could only take pictures from the outside because the site closes when it rains to preserve the documents it contains.

So instead we visited the interesting Armored Train Monument, commemorating a key battle in the Cuban Revolution. Revolutionary forces, led by Che, kept the Bautista government from resupplying the city with arms and soldiers when they captured an armored train from Havana.

The last evening in Havana includes a lively “Buena Vista Social Club”-like performance at Sociedad Cultural Rosalia de Castro, a perfect way to end the trip with Cuban music, dancing, and a final round of mojitos.

Plaza Major Trinidad

Final Thoughts: Is the Hola Cuba Tour Worth It?

Absolutely. This trip provides an immersive experience that goes beyond typical tourist activities. By staying in private homes, eating at family-run restaurants, and engaging with local artists, farmers, and historians, travelers support the Cuban people while gaining a deeper understanding of their way of life.

Cuba is a country that requires patience, adaptability, and an open mind. Things don’t always run on schedule, power outages are common. We missed our credit cards, constant connectivity, and drinkable water from the tap. But if you embrace the quirks, you’ll find a destination full of music, history, and unforgettable moments.

For U.S. travelers looking for a meaningful way to explore Cuba within legal travel restrictions, the Hola Cuba Intrepid tour is one of the best ways to experience the island’s charm, complexity, and resilience firsthand.

And of course, I would travel with listeners of the Amateur Traveler podcast anytime, anywhere.