TL;DR
- Today, four insurers price our example Cuba trip, from about S$47 to about S$805. The example is one adult aged 18 to 59, away for 14 days, on a single trip with no cruise.
- The gap between the lowest and highest premium is wide. Compare what each plan pays for medical bills and cancellation, not only the price.
- Most plans now include COVID-19 cover. Pre-existing medical conditions are usually excluded unless you declare them and the insurer accepts them.
- Cancellation cover only helps if the policy is in place before something goes wrong. So the time to buy is when you book.
- Your own price will move with how long you go, how old you are and who goes with you.
How much does travel insurance for Cuba cost from Singapore?
Today, for our example trip, premiums run from S$46.60 to S$804.75. That is what four insurers charge for the same trip on 23 October 2026. It is an example, not what you will pay.
For a sense of scale, take the same traveller on two weeks in Japan. There, 21 insurers price the trip, from S$32.40 to S$517.99. So for Cuba, fewer insurers quote, and the range sits higher at both ends.
What you actually pay depends on your dates, your age, who travels with you and the plan level you pick. The full list for today is on the Cuba price page.
What does the example trip assume?
It assumes one adult aged 18 to 59, staying 14 days in Cuba. The trip leaves in 30 days and is a single trip, with no cruise.
Change any of these and the price changes too. A longer stay, an older traveller or a second person all give you a different quote. The same goes if your Cuba trip is one leg of a longer journey.
The no-cruise point is worth noticing. If part of your holiday is on a ship, the example does not fit your trip. Get your own quote and check that the plan covers the cruise part.
Why is the gap between the lowest and highest premium so big?
Because the plans are not the same product. Most insurers sell two to four levels of cover. Higher levels pay more for medical bills, cancellation and lost bags, and they cost more.
When you search on the site, plans are listed from the lowest premium up. Each one shows the three benefits that differ most between them. That makes it easier to see what the extra dollars buy.
Where you land on that list depends on what you want covered. Think about how much you could pay yourself if a medical bill or a cancelled booking hit you.
What should I check on a plan for this trip?
The short answer is medical cover first, then cancellation, COVID-19 and any health conditions you have. Here is what each one means.
Medical cover overseas
This pays for treatment and hospital stays while you are away. It also covers emergency evacuation and getting you home. The limits differ between plans, so compare them on the Cuba price page.
Trip cancellation
This pays back what you cannot get back if you have to cancel for a covered reason. Illness or a death in the family are typical examples. Cover starts the day you buy. A plan bought the day before you fly gives you almost none of that protection.
COVID-19 cover
Most plans now include COVID-19 cover for medical bills and cancellation. Prices on the site include it unless you choose "Not needed" in the filters. If you switch that off, make sure you meant to.
Pre-existing conditions
Conditions you had before buying are usually not covered, unless you declare them and the insurer accepts them. A few plans do cover them, mostly on shorter single trips. You can find those with the filter on the results page.
Single trip or annual cover for a Cuba trip?
If Cuba is your only trip this year, a single-trip plan is the usual fit. If you travel more than about three weeks a year in total, an annual multi-trip plan usually costs less than buying single trips each time.
A single-trip plan runs from the day you leave Singapore until you return. Most insurers here cover a single trip of up to 90 or 182 days. Annual cover covers every trip in a year, each up to a set length, often 90 days.
With annual cover you pick a region instead of countries: ASEAN, Asia Pacific or worldwide. Pick the region that covers the furthest place you expect to go. Check that it includes Cuba before you pay. Which option suits you depends on how many trips are already on your calendar.
How do trip length and who travels change the price?
Longer trips cost more, and so do older travellers. Single-trip prices rise with the number of days. Insurers charge less for children and more for older travellers.
Some insurers stop covering travellers above 75, 80 or 85. The insurer confirms your age when you apply. So if you are bringing your parents, check the age limit on each plan before you go further.
For families, a plan covering two adults and their children usually costs less than separate plans. For couples, families and groups, we price plans from the insurers that offer a family or group plan. That means your list may look different from the one-adult example.
What does travel insurance not cover?
Every plan has exclusions. These are the common ones:
- Medical conditions you already had before buying, unless declared and accepted
- Travel to places the Ministry of Foreign Affairs advises against
- Losses while under the influence of alcohol or drugs
- Belongings left unattended in a public place
The Ministry of Foreign Affairs point catches people out. Check its advice for your destination when you book and again before you fly. The last point is the same habit as chope-ing a seat with your bag at a hawker centre. Overseas, a bag left alone like that may not be covered if it goes missing.
If something does go wrong, keep receipts, medical reports and any police report. Our Claims page walks through what insurers usually ask for.
What to do next
- See today's full list of premiums and benefits on the Cuba price page.
- Get a quote for your own dates, age and travellers on the travel insurance page.
- Put two plans next to each other on the compare page and check medical, cancellation and COVID-19 cover line by line.