Don’t miss our next Cuba Tour, 8 days scheduled for January 24- 31, 2026
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Tour Cuba in Compliance with OFAC and State Department Regulations
On our 8 Day Cuba Discovery Tour. State Department regulations require
Americans to go in compliance with one of 12 “reasons” to be allowed to visit Cuba. We visit “In Support of the Cuban People”.
Americans are prohibited from giving any money to the Cuban Government, which makes hotels, state owned restaurants, and public transportation off limits to our use. I scoured the metro Havana area to find a “Casa Particular” (think air bnb) that had enough rooms, AC in every room, private baths, and small hotel safes in every room. I also hunted to find a rare Cuban who had a van capable of moving a group of 10 people. I spent weeks traveling around Cuba putting together a great itinerary, one that doesn’t involve too much
travel time, meets our needs for great meals, has lots of things to do and involves interaction with Cuban People (a State Department requirement).
I’ve compiled a complete history of Cuba, their struggle under Spanish rule, their war of independence, life under dictator Batista (backed by the US Government), the Revolution under Fidel Castro, and the current situation in
Cuba. Our tour includes Old Havana including the main plazas and the forts, El Cabana and el Morro Fort (the third largest in the Americas) protecting Havana Harbor. Havana is a Unesco World Heritage site. We tour museums, hear great Cuban music, visit artesian markets, see the Museum of the Revolution as well as the Christopher Colombus Cemetery. We tour old Havana in 1950’s classic convertibles, visit the main Cathedral, do a walking tour in Old Havana with an expert Cuban historian. We eat great Cuban food, tour Havana Centro in Pedicabs, sometimes take a Salsa Dance class, stroll the famous oceanfront “Malecon”. We spend one day touring outside of Havana but still in the province of Havana. We will visit Fusterlandia, see embassy row, in Miramar, walk around the home of Ernest Hemingway, see the Cuban Missile crisis site and spend a day in either Artemis or Vinales, or both.
We also stay two nights at the famous Veradero Beach, again staying in Casa Particulars. We’ll use many forms of transportation; classic convertibles, horse drawn carriages, and even take a spin in a "coco taxi", shaped like a coconut.
We’ll eat delicious Lobster tails, fresh snapper and cuban specialties like flan, tostones, and yucca.
This tour is all inclusive, including all meals, all lodging, all in country transportation (except airfare), and all activity and entrance fees. Some highlights include the Capitolio (the cuban capital building), a replica of the US Whitehouse, the national theater, the famed malecon, the houses of Ernest Heminway and Che Gevera. We’ll see the bar "La Floradita", birthplace of
the Daquiri, and the Bogadita de Medio, home of the Mojito, Best of all is the interaction we have with the Cuban people, the Cuban culture, music, food, history, politics, art, and photo ops. We'll also visit Fábrica de Arte Cubano. Fábrica de Arte Cubano (FAC) is a large, interdisciplinary creative laboratory showcasing the best of contemporary Cuban art, with a strong social and community focus. A former oil factory transformed into a generalist space, it fosters exchange among the diverse artistic expressions that coexist within the same building. There are dance exhibitions, photography, music, contemporary art, food, and a variety of unique cultural experiences, all in one location.
Here are a few housekeeping details on visiting Cuba. The tour is $1,800 per person (there's a black Friday sale until the 25th of December, offering a discount on that price to $1,600). The tour includes all lodging, meals, transportation within Cuba, and activity fees. Go HERE to sign up for the tour, be sure to check the selected tour on the form. You will be booking a flight into Havana HAV airport code, and a flight out of Havana, HAV. Most flights are available on American Airlines, though Southwest and United also fly there. You typically have to go to each individual airline's websites to find flights to Havana, they are not listed on travel consolidator sites like Expedia, Travelocity or Orbitz. When booking a flight to Cuba, you must specify that you are visiting Cuba "in support of the Cuban people". The tour includes airport transfers in Havana. It does not include your airfare or alcoholic beverages.
This tour is about Cuban Culture, Music, Dance, Food, Art, History, Politics and Photo Ops. I've spent plenty of time in Havana and beyond and will provide a great glimpse into the Cuba of today, while keeping us OFAC compliant of the US regulations on travel to Cuba. We are traveling in support of the Cuban people and spend each day in activities providing interaction and cultural exchange with the Cuban people. We hire local Cuban guides, stay in Cuban owned homes and interact with the Cuban people. We partake in activities aimed at advancing Cuban human rights and encouraging the growth of a Cuban private sector independent of government control.
Americans were only recently allowed to resume travel to Cuba. We've had a complete embargo on Cuba since 1959, put in place under Kennedy, in response to the seizure of American owned assets. Historically the US backed Cuba's president Batista and tourism flourished from the prohibition era until Castro came to power. During this time US corporations and gangsters enjoyed Cuba's playground and built illicit businesses. When Castro came to power, he nationalized everything in Cuba, including many properties owned by Americans and US corporations. The embargo has remained ever since, along with a hostile cold war attitude. On December 17th, 2014, Obama opened Cuba to US visitors after 56 years of closure. Strong sentiment in the US, especially from the Republican party, has tempered any real attempt to end the economic embargo. When Trump was elected, he reinstated the travel restriction, but more importantly, he placed Cuba on a list of "sponsored terrorists", along with North Korea, Syria and Iran, making it more difficult than ever to undo the embargo. Strict travel restrictions were again put in place in 2017, under Trump.
Biden reopened Cuba to American tourism but on a more limited scale than Obama, and when Trump was elected for a second term, he left open the option to visit. Cuba travel remains restricted since there's concern about having funds end up in the hands of Cuba's communist government. There's a strong faction in the US that continues to support the economic embargo. Recently, Miguel Díaz-Canel, the current Cuban president, has broadened the list of small businesses that Cubans can operate. The change in policy was brought on by a nearly stalled economy but the US sees it as a move toward a more democratic center. Cuba still maintains tight control over dissidents and it puts any further relaxation of US policy to Cuba at an impasse. Trump has placed limitations on doing business with Cuba. Under Obama, cruise ships from the US were able to visit Cuba, but those days are gone. Obama was not concerned about being re-elected when he made his changes to Cuban policy. Currently Cuba is more difficult than ever to visit but we run our tour in complete compliance with OFAC and State Department rules.
We plan to visit one of the other amazing Cabarets in Havana, depending on which will allow compliance with OFAC. Some of the group may take a salsa dance class, depending on the interests of the group, followed by another tour on foot in old Havana. Depending on time, we'll end the tour one day with a tour of the Morro Castle, a nearly 500 year old fort that guards the entrance to Havana Harbor.
We also visit to Matanzas on our way to Varadero Beach. Matanzas has a great art walk and a few interesting buildings to see along the way. In Varadero, we'll visit local restaurants, a local art gallery or two, a large artesian market (or two) and of course we'll see the famous Varadero Beach, awarded the world's best beach by TripAdvisor's travelers choice in 2019. We have a great group of local Cuban guides who work with us throughout the trip. We'll also head to Calle 62 (a great local restaurant) after visiting the Varadero crafts market. We'll be staying in a local Casa particular in Varadero. We'll have a quick stop at the house of the Beatles and that evening we'll head to Calle 62 for a look at an zone run by the Cuban Government tourist ministry. We may see a local salsa dance team doing a great show at Calle 62.
Day 6: We'll spend another day in Varadero, enjoying the low key vibe, meet local Cubans and shop from local vendors. We'll jump on our collectivo and see the hotel zone complete with well known branded all inclusive resorts that cater to the Canadian and European market. Our economic embargo rules make these hotels off limits to Americans. We also visit Parque Josone Varadero, depending on time. This mansion was built by an eccentric Spaniard, owner of the Arrechavala rum factory. The park features a lagoon turned into a man made lake that's home to a variety of migrating birds, complete with an arched bridge. the owner built a tunnel 60 meters long that leads to Vadadero beach. Along with the neoclassic style mansion built by the owner, there's a variety of restaurants. We sometimes visit a small museum about Varadero as well. Later that afternoon we'll head back to Havana.
We'll tour more of Havana on Day 7, We'll visit the Hotel National, the hangout for gangsters in the 50's, and visit Salón 1930 ‘Compay Segundo' in the hotel, a music venue that hosted the Buena Vista Social Club. That evening we'll have dinner and see a famed Cuban Cabaret, a spectacular of Cuban music and dance.
On day 8, we will arrange transportation to the airport, depending on the time of your flight. Breakfast is included, as well as transportation to the airport.