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Cuba doesn't generally give out travel visa to the United States except in special circumstances, and for a US citizen to travel to Cuba is a federal crime.
My best advice to you is to travel around the country, stay one day in a hotel and the other in a Casa Particular where you will be a guest in a Cuban family's home.
Hire a car or take the Viazul Bus, Cuba is easy to do on your own and much cheaper when you arrange it yourself. Let a local hero make a tailor made personalized itinerary for you including maps and receive the whole trip in an offline working app for your phone.
The best time to travel to Cuba is between November and April, after the rains of the wet season and before the hot and sticky discomfort of the summer months.
Generally April and November -the transitional months between the two seasons- are particularly pleasant (weather-wise) because of the hot (day and night) and sunny weather but without being too hot or humid, with almost no risk of cold fronts, and not too much rain.
Remember, how frustrating it was when you were a kid and you couldn't reach the cookies on the top shelf?