Best Time to Travel: Nice tropical weather all year round, but January through March might be the best time given the lower humidity, less rain, and cooler nights.
Highlights: In addition to all the attractions and rich culture, Havana is very safe.
Havana’s beauty has been attracting visitors ever since its foundation in 1519. Americans in particular found it to be a little piece of heaven early in the 20th century until the revolution, when traveling there from the US came to an end, legally. Even then, many found ways to make the journey (technically illegal), it was simply too hard to resist its magic. Now a days, thanks to a general license approved by the government, some travel is authorized; enough to make it possible for many American to taste a little bit of heaven again.
Havana has enough to entertain visitors for more than a week, but if all you have is 3 nights / 4 days, these are some of the things you can do to make the best use of your time.
First of all, have airport transportation ready. Arriving at the Jose Marti International Airport without a car reservation can be a bit chaotic, especially at terminal 3. Plus, drivers are usually happy to welcome you and share tips and stories. The airport is outside the city, so you will get the chance to see the outskirts during the usually 45-minute long drive.
DAY ONE: Once you are settled, you are ready to explore the city! One of my favorite ways to get started is walking old town. Cuba went from colonization to independence, to dictatorship, and then revolution in less than 60 years. Few countries in the world have had such a hectic history and a pretty intact old town that can still tell it.
Walking through its narrow streets and plazas, while listening to stories, facts, and legends from an independent guide is the perfect introduction to La Habana. I recommend trying food from street vendors, checking out privately owned stores and cafes, stopping for a drink while listening to live music, and ending the walk at one of the many rooftops around to enjoy the sunset.
DAY TWO: There are many ways to spend your second day in Havana. I personally like to see as much of the country as possible when visiting new places for just few days. Therefore, I suggest exploring outside the city one day. The countryside in Cuba tells a big part of the Cuban story, plus is full of breathtaking views, prehistoric sites, and natural wonders.
Places like Viñales have all these, plus are great examples of how small towns are growing thanks to the direct impact from foreigners. The government never developed touristic infrastructure in these areas, so it’s been up to the residents to welcome, host, and entertain visitors. You could visit tobacco plantations, bee and honey farms, and caves. Maybe go horseback riding while also supporting regional small private businesses.
DAY THREE: Havana is a large capital city. Full of parks, boulevards, architectural masterpieces, and history throughout. There is simply no better way to see it than cruising the city onboard a classic car accompanied by a native who can tell you all about it. A good driver/guide would know the city very well, and is always excited to show it to visitors.
This journey across the city is literally a trip down memory lane. You learn about Cuban history pre and post revolution, and visit places of interest like the Colon Cemetery, Revolution Plaza, The Havana Christ, Vedado neighborhood, Habana’s own 5th avenue and the gorgeous Bosque de la Habana. Most importantly, you get to see how the past and present have mixed to create a metropolis like no other in the world.
Do this either early in the morning or late afternoon to avoid the hottest hours of the day. Doing the classic car tour the last day during short visits is a nice way to get a taste of additional things the city has to offer, and hopefully make you wanna say “until the next time” instead of goodbye.
DAY FOUR: Depending on your flight schedule, this last day will be the perfect time to do some shopping and get last minute selfies while walking along the Malecon or main boulevards before departing towards the airport.
Now the legal stuff: traveling to Cuba is authorized only under a general licence that grants travel under 12 specific circumstances. The average traveler would use “Support to the Cuban People” as their reason for traveling, but this would change case by case. Travel consultants like me at Ursula Hosting, are able to plan trips for clients by following guidelines from the government and working with independent vendors and providers to offer full time programs with activities and experiences. By doing so, we promote meaningful contact with Cuban people, support civil society in Cuba, and promote the Cuban people's independence from Cuban authorities.
Travelers can plan their own trips, but they must understand all requirements and develop and record full time schedules. They must also be able to show proof of these schedules and programs since the government has up to five years to audit travelers.
I am always happy to provide additional information and tips. Havana is one of my favorite destinations!!