How can I plan a memorable first trip to Cuba without rushing?

The Office of Foreign Assets Control authorizes travel under general or specific licenses for the 12 categories of activity listed in 31 CFR § 515.560(a): family visits; official US government, foreign government and certain intergovernmental business; journalistic activity; professional research; educational activities; religious activities; amateur or semi-professional athletic competitions; support for the Cuban people; humanitarian projects; activities of private foundations or research or educational institutes; exporting, importing or transmitting information materials; and certain authorized export transactions. Anyone relying on a general authorization must retain specific records relating to the authorized travel transactions, under the requirements at 31 CFR §§ 501.601 and 501.602.

Several of those categories changed recently, and the changes are material. OFAC's guidance records that, as of 30 September 2026, authorization for professional meetings or conferences in Cuba was removed; certain educational travel must now take place under a US-subject sponsoring organization with an accompanying representative; and group people-to-people educational travel was removed entirely. There are also restrictions on lodging at properties identified by the State Department and on certain financial transactions with entities on the Cuba Restricted List. A trip designed on pre-2026 guidance may no longer be authorized.

Beyond the paperwork, the Department of State has Cuba at Level 2, Exercise Increased Caution, issued 7 May 2025. It recommends enrolling in the Smart Traveler Enrollment Program for embassy alerts, and buying travel insurance that covers evacuation, medical care and trip cancellation — advice that carries more weight here than in many destinations because of the limits on US financial transactions on the island.

The recordkeeping obligation is the part travelers forget, and it outlives the trip. A general license is self-certifying at the point of travel but auditable afterwards, which means itineraries, receipts and evidence of qualifying activity need to be kept rather than discarded at the airport. Choosing independent accommodation and independent restaurants is not only a cultural preference under the support-for-the-Cuban-people category; it is also what the records have to show.

• Before booking — Identify which of the 12 categories your travel falls under, and confirm the current terms of that category rather than relying on earlier guidance.
• While traveling — Keep a dated record of activities and spending as you go; reconstructing it later is far harder.
• On the ground — Plan each day around independent businesses, which satisfies both the category and the practical reality of limited US card access.

Three things, in order of likely impact. Lodging restrictions mean certain hotels are off-limits to US travelers, and the State Department publishes the list that determines which. Power is unreliable enough that itineraries should assume interruption rather than treat it as an exception. And the hurricane season officially runs to 30 November, though the National Hurricane Center notes activity sometimes occurs before and after those dates — a relevant caveat for anyone building a trip in late spring or early December around non-refundable arrangements.

The when-to-visit question in this chapter gives Havana's seasonal figures and the outage pattern that shapes a day there, and the places question maps the provincial sites an independent itinerary can be built around.