UPDATE—June 2019: Cuba is currently changing very rapidly. The information formerly on this page regarding “charter flights” no longer applies. You can now book your flights to Cuba from many U.S. airports on five different U.S. Airlines: American, Delta, JetBlue, Southwest, and United Airlines. Each airline will only ask that you sign a Travel Affidavit that indicates you will not be a Tourist. FYI: JetBlue, Southwest, and United Airlines are ADDING 30 flights a week, beginning in the fall. Perhaps their CEO’s know something that is not common knowledge.
You can also book and pay for your housing by going to AirBnB.com and see what is available in each city. I recommend searching for, booking and paying for a place in “Old Havana” or “Vedado” for your first 2-3 nights. After that, you can wing it. Each BnB owner will be able to suggest nearby things to see and do. They will also recommend BnB’s in other areas.
In the summer of 2017, President Trump said he would change guidelines regarding travel to Cuba. Many pages of “new” guidelines have been published, but as a practical matter, very little has changed. It is now a little more complicated for single individuals to travel to Cuba. I would not hesitate to recommend to friends and family members to visit Cuba as an individual. (Once there, visit the travel agency at any large hotel and sign up for a half-day group tour, such as a visit to Hemingway’s Country Estate. You would then be qualified as a “Group Traveler”—not that anybody cares. There is no way for any government official to prove you are traveling illegally.)
Group travel guidelines essentially have not changed, and a “group” consists of as few as two people. For more information on individual travel, please go to my Cuba Newsletter and scroll down to the article I wrote for December 10, 2016. https://www.jameslewisrn.com/blog
Miscellaneous Notes: My favorite guidebook is Moon Handbooks: Cuba, by Christopher Baker. A terrific to download and use offline is the one by Cuba Travel Services. It includes a GPS map and locator that can be used offline.
Cuba has the same general climate as Hawaii. It’s hot in the summer, but manageable if you like warm climates. You can go on morning tours and stay out late at night listening to music. (Remember Havana is one of the safest major cities in the world for visitors.) You can spend afternoons in the shade by the pool or beach, or reading/napping in your air-conditioned hotel.
I have never been overly concerned about hurricane season, which peaks in August and September. Would you not visit Miami during those months, or not visit San Francisco because it has earthquakes? At least you will be warned about hurricanes 3-4 days in advance in any particular area. The Cubans are very good at managing hurricane evacuation and relocation, especially with regards to tourists—their number one source of revenue. In general, as the fall becomes winter, the weather improves in Cuba while it gets colder in the States, and each month brings more visitors. If you decide today to visit Cuba, you can legally travel there tomorrow with a General License, have a great time, and return with no hassles. Call or email us if you have any questions.