Best Cayman Islands Travel Insurance Plans & Coverage
Written By 
Reviewed By Last updated: 03/12/2026
Key Takeaways
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In the last 12 months on Squaremouth, the top three travel insurance plans purchased by travelers with upcoming trips to the Cayman Islands are offered by: Tin Leg, IMG, and Travel Insured International.
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U.S. travel insurance is not accepted throughout the Cayman Islands, which is why many travelers prioritize plans that include strong travel medical coverage.
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Try our online travel insurance comparison tool to get quotes from multiple providers at once. For personal assistance, call our award-winning agents at 1-800-240-0369.
Squaremouth’s the Cayman Islands Travel Insurance Recommendations
Over the last 12 months, the top three travel insurance plans purchased by travelers with upcoming trips to the Cayman Islands on Squaremouth were:
Although the Cayman Islands no longer requires travel insurance, Squaremouth still recommends at least $50,000 in Emergency Medical coverage for international travelers. Squaremouth also recommends travelers search for a travel insurance policy with at least $100,000 in Medical Evacuation coverage. Medical Evacuation can cover the cost of an evacuation to the nearest hospital in the event of an emergency.
In addition to these benefits, Squaremouth recommends a comprehensive travel insurance policy that includes other benefits for the most common travel insurance concerns. Primarily, this includes Trip Cancellation coverage and coverage for delays and luggage, among other benefits.
For travelers who are concerned about losing their prepaid trip expenses if they need to cancel their trip to the Cayman Islands, Squaremouth recommends insuring these costs through the Trip Cancellation benefit. This benefit can reimburse 100% of a traveler’s prepaid and non-refundable trip costs if they need to cancel for a covered reason, such as not being able to travel because they are sick.
Click here to begin your search for Cayman Island Travel Insurance.
More Details on the Best Travel Insurance for the Cayman Islands
Best Overall Medical Coverage
Medical / Med Evac Coverage
$500,000 / $500,000Cancellation / Interruption Limits
100% / 150% of trip cost
The top-selling travel insurance plan on Squaremouth, accounting for roughly 13% of all policy sales
Comes standard with $500,000 in Emergency Medical and Medical Evacuation coverage, which is among the highest offered by any comprehensive travel insurance plan
Includes 100% Trip Cancellation protection, which reimburses up to $30,000 in trip expenses per traveler in the event of a covered cancellation
Best Overall Cruise Insurance
Medical / Med Evac Coverage
$100,000 / $500,000Cancellation / Interruption Limits
100% / 150% of trip cost
Selected by over 22% of Squaremouth cruisers, making it the most popular option
Offers up to $100,000 in Emergency Medical coverage and $500,000 in Medical Evacuation coverage, surpassing our coverage recommendations for cruise vacations
Plans have the option to add CFAR and IFAR coverage, which can add the most possible flexibility and additional peace of mind heading into a cruise
*Features strong comprehensive coverage with the most important benefits for cruisers
Best Overall Family Travel Insurance
Medical / Med Evac Coverage
$100,000 / $500,000Cancellation / Interruption Limits
100% / 150% of trip cost
Features the most generous ‘Free Coverage for Kids’ pricing, allowing up to 9 children to be covered at no additional cost for an insured adult
The most popular family plan, chosen by roughly 14% of families insuring trips through Squaremouth
The customization options, well-rounded coverage, and up to $500,000 in medical coverage also make FlexiPAX our pick for ‘Best International Travel Insurance For Families’
The only family plan on Squaremouth that offers the optional Cancel For Any Reason (CFAR) and Interruption for Any Reason (IFAR) upgrades, providing the most possible flexibility for families
Cayman Islands Travel Insurance Trends and Data
The Cayman Islands are known for some of the best beaches in the world, with white sands and calm and clear water.
Destination Rank: 59
Percentage of Squaremouth Sales: 0.37%
Average Premium: $228.13
Average Trip Cost: $3,529.31
Squaremouth Analytics compares thousands of travel insurance policies over the last two years to identify changes and trends in the travel insurance industry.