Travelers frequently flock to Cuba whenever their schedules allow it; however, "the best time to visit Cuba" is during the dry season — November to April.
U.S. citizens can find flights direct from Florida to Havana, a major boon when considering that Cuba is only 90 miles (145 km) from Key West. Many airlines offer flights from major U.S. cities that stop in Mexico.
The two major airports in Cuba are Antonio Maceo Airport (SCU) and Jose Martí International Airport (HAV), though most international flights will fly into the latter. Jose Martí is located 9 miles (14 km) outside Havana, which means a 20-minute taxi ride into the city with one of the airport’s approved taxi services – you can choose from either Taxi OK or Panataxi. Panataxi is a bit more expensive than the former, but typically travelers should expect to pay around 15 CUC (15.01 USD).
Bus transportation from the airport into Havana can be difficult, as there is no set timetable. Once in Havana, however, there are double-decker busses that cater to tourists.
For travelers who want to travel to Santiago de Cuba from Havana, a flight into Antonio Maceo (539 miles/867 km apart) may be preferable to an 11-hour bus ride. Domestic flights to Santagio leave from Jose Martí every day via Aerogaviota or Cubana Air.
Cruises leave to Cuba from several countries, including Ecuador, the Bahamas, and even Greece. Many of these cruises are operated by companies in the U.K. or Canada. Only a cruise line that registers its U.S. citizens as part of a nonprofit – e.g., the ship is bringing medical supplies to Cuban people – can offer legal travel for them.
Negotiations are underway for establishing a ferry route between Florida and Cuba.
If you are considering sailing from Florida to Cuba on your own, it’s best to heed Ernest Hemmingway’s famous words: "Brother, don't let anybody tell you there isn't plenty of water between Havana and Key West.”
When you finally make your way to Cuba, you will have plenty of options for getting around the island, but keep in mind, some methods are better than others. This island nation may seem small, but don't take it's size for granted. Getting from one end of Cuba to the other will take time, effort, and planning.