TRAVEL & RENTAL CAR INSURANCE
 
These are expensive vacations and it can be a prudent idea to have at least a minimum level of insurance for the unforeseen. Basic trip interruption insurance costs about 5% of the total cost of the travel arrangements, and provides a lost baggage, delayed travel and basic medical expense/evacuation benefit as well.

The more family members that are traveling, the older the family member(s) and lastly the health of a particular family member all increase the probability of needing insurance. Additionally, your domestic medical insurance may not provide a medical benefit in a foreign country-- and it surely won't provide coverage for emergency evacuation to a USA (Miami) hospital. Air Evacuation does cost between $20,000 - $30,000; depending on what medical care you need during the flight.

Last minute illness or hospitalization, airline strike/bankruptcy, weather delays can all cause disruption and/or economic harm.
 

I.     TRIP CANCELLATION/INTERRUPTION INSURANCE

(Click This Link Below)

 
2. RENTAL CAR INSURANCE
 
Unrelated to travel/interruption/medical insurances above-- when you rent a car/van on Grand Cayman; you will be asked whether you would like to accept/pay for a number of confusing insurance coverages--
 
I have excerpted the insurance page from Andy's rental car webpage below-- you can see that it can be confusing. Andy's is a great rental car company--all of them have similar plans.
 
FULL COVERAGE (price varies by vehicle class) - Available to drivers aged 26 to 65. Covers damages to ANDY'S vehicle during the course of the rental contract. This Option also covers 3rd-Party vehicle/property damages up to $297,000 and 3rd-Party bodily injury up to $5,900,000 per accident. (see NOTE below)

NOTE: ANDY'S Loss Damage Waiver Policies are valid during the normal course of driving and will be deemed VOID if renter or any additional driver is using the vehicle in violation of any Laws of the Cayman Islands or fails to adhere to Terms and Conditions of ANDY'S RENTAL AGREEMENT. Damages caused by negligence, abuse, unauthorised drivers and isolated "ACTS OF GOD"(falling coconuts, etc) are NOT covered by any of ANDY'S Loss Damage Waiver Policies**

DEDUCTIBLE COVERAGE (price varies by vehicle class) - Available to drivers aged 21 to 65. Covers damages to ANDY'S vehicle, with a $1000 deductible. In the case of damages to ANDY'S vehicle, hirer is required to pay up to a total of $1000. This Option also covers 3rd-Party vehicle/property damages up to $297,000 and 3rd-Party bodily injury up to $5,900,000 per accident. (see NOTE above)

THIRD-PARTY LIABILITY COVERAGE ($5.00/day) - Available to drivers of all ages. This Option covers 3rd-Party vehicle/property damages up to $297,000 and 3rd-Party bodily injury up to $5,900,000 per accident. Hirer is responsible for ALL damages to ANDY'S vehicle. (see NOTE above)

DEDUCTIBLE COVERAGE 65+ ($9.00/day) - Available to drivers over 65 years of age. Covers damages to ANDY'S vehicle, with a $1212 deductible. In the case of damages to ANDY'S vehicle, hirer is required to pay up to a total of $1212. This Option also covers 3rd-Party vehicle/property damages up to $297,000 and 3rd-Party bodily injury up to $5,900,000 per accident. (see NOTE above)

 
My recommendation to you is to use AMERICAN EXPRESS to make your car reservation. AMEX provides you with coverage. They recommend just declining the collision damage waiver. This will save you as much as $15/day on your rental car.

Amex doesn't cover you in all countries-- Australia, Ireland, Italy, Israel, Jamaica and New Zealand are excluded.

You might call American Express at 1-800-338-1670 with any specific questions.

 
Some Gold/Platinum Card Visa Programs also provide coverage-- but I have heard that they will not cover the 9 passenger Hyundai H-1 Vans on Grand Cayman (viewed as a commercial vehicle). Check your own cardmember benefits.