The Caribbean looks idyllic, but travel insurance here matters more than most people expect. Medical costs across the region — particularly in Barbados, the Cayman Islands, and the Bahamas — are among the highest in the world. A hospital stay can run to thousands of pounds per night without cover. Hurricane season runs June to November, adding cancellation risk. The right policy makes all of this manageable.
What to look for in Caribbean travel insurance:
Medical cover is the most important factor. Look for a minimum of £2 million in medical evacuation cover. If something serious happens in a smaller island with limited facilities, you may need to be flown to the US or UK for treatment — that flight alone can cost £30,000+. Most good policies cover this automatically. Cheap policies often don't.
Hurricane and weather cancellation cover. If you're travelling between June and November, make sure your policy covers cancellation due to hurricanes. Read the small print: many policies only cover you if the hurricane is at your destination, not if it disrupts connecting flights or causes you to miss your departure. Look for 'FCDO warning' cover — if the UK government advises against travel, the policy pays out.
Cruise cover. If your Caribbean trip includes a cruise, ensure your policy is cruise-specific or includes missed port cover. Standard travel insurance often excludes cruise-specific claims.
Top-rated providers for Caribbean holidays in 2026:
Staysure is consistently rated highly for Caribbean destinations. Strong medical limits, decent cancellation cover, and clear hurricane clauses. Good option for families and over-50s.
Insure & Go provides competitive Caribbean-specific policies with solid emergency medical cover and 24/7 assistance lines. Their annual multi-trip policies are worth it if you visit the Caribbean more than once a year.
Allianz Travel is frequently recommended for high-value trips. Their Premier tier includes £10m medical cover and strong cancellation protection including weather events.
Avoid: very cheap comparison site policies that include Caribbean destinations but have low medical limits (under £1m). They look attractive but leave you massively exposed if something goes wrong.
Always check: Does the policy cover pre-existing conditions? Many standard policies exclude them. If you have any medical history, declare it upfront — claims get denied when providers discover undisclosed conditions.
Compare Caribbean travel insurance policies at caribcompare.com — side by side, with key limits clearly shown.