The policy excludes the country
Plenty of ordinary travel policies exclude Cuba by name. Nobody notices until a border official asks for the certificate, and by then the flight has landed.
Travel insurance
One plan, written for travel anywhere in Latin America and priced per person per day. Cuba requires cover to let you in and can ask to see it at the border. The policy that fails there is almost never the one somebody forgot to buy: it is the one that excluded Cuba in a line nobody read.
None of these looks like a problem until the moment it matters, which is exactly why they are worth an hour of your attention now.
Plenty of ordinary travel policies exclude Cuba by name. Nobody notices until a border official asks for the certificate, and by then the flight has landed.
Diving, riding, altitude and hired vehicles sit outside a lot of standard cover. If it is on your itinerary it needs to be on your policy.
Cover that ends the morning of your return flight ends too early. It has to run to the day you land back.
Medical repatriation is the largest bill a traveller can face. It is the number on the policy worth actually reading.

Heyo Travel is a tour operator, not an insurer. What we do is arrange cover before you depart and confirm that it satisfies the country you are entering. What a policy pays, and on what terms, is between you and the underwriter, and we will always tell you to read it.
The first two decide whether you get in and whether you are treated. The rest decide what it costs you afterwards.
Every figure below is the insurer’s own, in USD, per insured traveller. Where the schedule says a limit sits inside the global maximum, it says so here too, because a figure that shares a pot is not the same as a figure that has one.
This is a summary of the schedule as issued, for reading before you buy. The policy wording the insurer sends you is the contract, and where the two differ the wording is what counts.
Yes. Cuba requires travel medical insurance that is valid in the country, and it can be asked for at the border. This is not a recommendation we are making; it is a condition of entry.
Because the premium is per person per day, and it moves with the age of each traveller at departure and with what you plan to do out there. A single headline figure would be right for one party and wrong for every other. Give the search your dates and who is going and it prices the actual policy.
Of course, provided it is valid in the country you are entering. Read the exclusions rather than the summary, because Cuba is usually excluded in the exclusions and not mentioned anywhere else.
Sometimes, and it is worth checking the wording rather than assuming. Card cover often has conditions attached, such as booking the trip on that card, and often excludes the same countries a cheap policy does.
Tell us where you are going and we arrange insurance that is valid there, before you travel.