I grew up 264 miles from Cuba and until visiting never fully understood the history and impact of the political landscape on its people and culture. The history, the time warp photos, the rum and cigars, the proximity to the US and the mystery of this country make it an enticing travel destination. Here’s our itinerary for a long weekend getaway and 10 honest insights for anyone thinking about planning a trip to Cuba.

Our Itinerary

Day 1:

• Flight arrives 16:10 to Havana Airport. Account for at least an hour to get through border patrol and security inspections.
• 30 min taxi to old Havana. Check into AirBnB. We stayed on Havana Street in Old Havana which was a really great location and had this nice balcony. Our place is no longer listed but this one is in the same building for reference.
• Drink mojitos like Hemmingway at La Bodeguita Del Medio
• Dinner at El Cocinero. Really cool outdoor dining spot and great food. Make reservations in advance.

Day 2:

• 9am – Noon: Convertible tour of Havana.
• Lunch at Paladar Dona Eutimia which was a great spot near the Sao Cristovao Cathedral.
• Explored Old Havana, Shopped the San Jose Market, Stopped along the way for Cuba Libres (local rum and coke) and Mojitos.
• Sunset along El Malecon. Walked the Malecon to Hotel Nacional de Cuba for appetizers, cigars and mojitos pre dinner.
• Dinner at La Guardia. Beautiful grand staircase entrance. Accepted USD and food was decent. Must make reservations in advance.
• Sangria at a little patio along Calle Pena Pobre right by our AirBnB.

Day 3:

• Full day horseback riding and tobacco farm adventure in Vinales Region. Booked with Riding Vinales.
• Private driver hired with our tour picked us up at our AirBnB at 7am. 2.5 hour drive to Vinales. We all slept most the way.
• The four of us had our own guide who took us through the Vinales region each of us on our own horse.
• We stopped at a small lake for a mojito break. Then made our way to a Tobacco farm. They taught us all about their process and gave us farm rolled cigars to smoke. They also provided a nice lunch before we headed back on our horses.
• Our driver drove us back to our AirBnB in Havana. We were back around 18:00.
• Famous daquiris at El Floridita.
• Dinner at Ivan Chef Justo. Food was good not amazing, but avoid the tacos. It had a cool roof top patio where we requested to sit. Our reservation was at 21:30 and it felt as though they were rushing us to get out so I’d book an earlier reservation if you chose to go here.

Day 4:

• We drove to Varadero via a hired private driver (2 hours). We hoped to scuba dive there, but high winds cancelled our dive trip.
• Rented a scooter and explored the small beach town peninsula of Varadero.
• Stopped at the beach which is very large and has many access points along the main road.
• Went cigar and rum shopping for friends and family.
• Food and bar crawl for dinner. There are many places to eat along the main road in Varadero and prices are much better then Havana.
• Ended the night at “The Beatles” bar which had raging band covering pink Floyd, Bon Jovi, ACDC and more. It was definitely the spot to end the night in Veradero.

Day 5:

• Drive back to Havana.
• Lunch in Havana.
• Flight to Houston at 17:10

Before planning a trip- Read my top 10 takeaways:

1. To go or not to go? I found it to be a very memorable, fun and also educational weekend getaway. You can see from all my photos it is a beautiful country from the mountainous region to the historic old Havana. It is eye-opening in many ways and a great reminder that Capitalism is a blessing that we must protect. The morality of visiting Cuba may be your decision maker and I hope this post helps shed some light on that aspect. In some ways tourist, specifically those seeking to support private businesses, are helping promote the only glimmer of hope for budding capitalism. On the other hand there is no getting around supporting the government through the fees you pay at currency exchange to the fees private businesses must pay which come from your business.
2. It was incredibly easy to get in and out of Cuba. We visited under the “Supporting the Local People” general provision for Americans travelling to Cuba. Online it said we needed an hour by hour itinerary showing how we would be supporting the local people, including what restaurants we’d be eating at and which casa particulars we’d be staying at. This was never requested by any security, visa agency or border patrol. The gate agent in Houston who we purchased the visa from simply asked which of the 12 reasons we were travelling for and issued us our visas.
3. There are as many old cars as it looks like in tourist photos. They are the main form of transportation everywhere. All private cars we hired in advance were vintage American classics as well. There are some newer cars brought in for government owned taxi services and car rentals. Locals are very proud of their vehicles which have been passed on through their family for years.
4. The communist government still very much rules everything. In recent years Cubans have been allowed to form their own businesses. These businesses, however, are never fully owned by the people. The government retains 51% ownership of any new business that is formed in Cuba. The government is also the sole source for hiring. “Business owners” can not hire employees directly. They must pay the government for employees and the government will take a large cut of the pay and give a small portion to the employee.
5. The average salary for most is so low that people are solely dependent on the government for necessities and can not afford internet, maintain their homes or any other luxuries. Because the government controls all professional salaries, it is looked down on to be a doctor, lawyer, engineer or any other professional. Our local guide told us that they make such little money that they are unmotivated and many leave their profession to seek opportunities in tourism – the only industry it seemed with the potential to make money.
6. New businesses mainly rely on tourism which greatly increased when the Obama administration opened the doors for Americans and cruise ships to Cuba. That tourism drastically decreased when the Trump administration put tighter restrictions on travel to Cuba and restricted all cruise ships. Trump also created a restricted list of businesses Americans can not support while visiting Cuba. That list includes almost all hotels, many stores and any entities serving the Defense and Security sectors. This is important because the government continues to spend the people’s money to build new hotels while Cubans are living in 60 year old crumbling buildings right next door with no money to repair them. I was glad we had to stay with local Airbnb owners rather then support this corrupt government.
7. Prices were higher then expected for everything and the exchange rate with fees was awful. It became very apparent that even as visitors intent on supporting the local people through private businesses (ie: private drivers and tour guides, Airbnb’s) you can’t get around funding the government. It wasn’t adding up why we were paying such high prices for things like taxis and drinks and food if the people are so poor. We learned that so much of the money is taken by the government in the form of licensing fees, or business fees that it drives tourist prices up without the people seeing any significant gains.
8. Scammers and people doing whatever trick to beg for money are very prevalent in Havana. We were constantly bothered by people wanting to sing for us or take us to buy overpriced drinks that they’d get a cut of, or take a picture with props. At first locals seem so friendly and welcoming, but it was usually for a reason and for the most part they are all trying to work anyone who looks like a tourist. Our private drivers and Airbnb host were definitely the exception to this. You have to take it in stride and remember you’re there to support the people and maybe that’s the only true form of capitalism is street performers or picture takers because at least they are getting the money not the government.
9. The lifestyle seemed much more pleasant as we left Havana and explored the Vinales region. Farms had been kept in the same family for 100s of years and they definitely appeared to be the lucky ones with a very modest but peaceful life and plenty of farm rolled cigars. I definitely recommend taking a day trip to Vinales.
10. Havana has soo much potential. It is a city stuck in the 1950’s which provides amazing architecture and colorful city blocks. Then there are sections that have completely crumbled because it has not been maintained.

If you have any further questions about traveling to Cuba ask in the comments!