Best Cayman Islands Travel Insurance Plans & Coverage
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Reviewed By Last updated: 03/26/2026
Key Takeaways
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In the last 12 months on Squaremouth, the most popular Cayman Islands travel insurance plans are offered by Tin Leg, IMG, and Travel Insured International.
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Medical care in the Cayman Islands is high-quality but generally expensive for Americans, as U.S. health insurance is not accepted by private or public medical facilities.
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Cayman Islands travel insurance costs $229 on average, with an average trip length of 9 days. With that in mind, you can expect to pay $25 per day on coverage for your trip.
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The Cayman Islands are home to world-class scuba diving and snorkeling, but these adventure activities are often seen as high-risk by providers and typically require specialized coverage.
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Hurricane season in the Cayman Islands runs from June to November. Many comprehensive travel insurance plans can cover cancellations, delays, and other disruptions caused by severe weather.
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Try our online travel insurance comparison tool to get Cayman Islands travel insurance 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
Most Popular Cayman Islands Policy
Medical / Med Evac Coverage
$500,000 / $500,000Cancellation / Interruption Limits
100% / 150% of trip cost
The top-selling policy among Squaremouth customers visiting the Cayman Islands, accounting for 19% of all policy sales for the destination
Covers over 250 sports and activities, including popular watersports like snorkeling, kiteboarding, and jet skiing
Features among the highest-rated 24-Hour Emergency Assistance services to policyholders, which can help refer you to quality medical care on the island, coordinate evacuations back to the United States, or provide emergency cash transfers
Best Coverage for Caribbean Cruises
Medical / Med Evac Coverage
$100,000 / $500,000Cancellation / Interruption Limits
100% / 150% of trip cost
Includes up to $500,000 in Medical Evacuation coverage, which can cover the cost to transport you from a cruise ship to a nearby medical facility on land
Features up to $500 per person in Missed Connection coverage per person, which can cover the cost to make new travel arrangements if you miss your Cayman Island cruise departure due to a covered delay in your travel itinerary
Offers up to $100,000 in Non-Medical Evacuation coverage, which covers expenses to get you to a place of safety in the event of a hurricane at your destination
Covers travelers up to 99 years old, making it a great option for senior travelers visiting the Cayman Islands
Best Plan for Families
Medical / Med Evac Coverage
$100,000 / $500,000Cancellation / Interruption Limits
100% / 150% of trip cost
Allows families visiting the Cayman Islands to insure children at no additional cost, providing significant cost savings to large families planning a Caribbean getaway
Offers numerous ways to enhance your coverage, such as popular add-ons like Cancel For Any Reason (CFAR), Interruption For Any Reason (IFAR), and Rental Car Damage protection
Includes complimentary concierge services to all policyholders, which can assist in making beachfront dinner reservations, arranging island excursions, or coordinating airport transfers
Features up to $1,000 in Baggage Loss protection, which can reimburse you for personal items that are lost, stolen, or damaged during your time in the Cayman Islands
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: 61
Percentage of Squaremouth Sales: 0.36%
Average Premium: $231.95
Average Trip Cost: $3,573.76
Squaremouth Analytics compares thousands of travel insurance policies over the last two years to identify changes and trends in the travel insurance industry.