First, verify what your personal insurance covers outside the US. Depends on if you are over 60 or over 65. Over 65, those on Medicare have zero coverage outside the US from Medicare. We personally have a Medicare Supplement that covers 80% outside the US.

Once you verify what your personal insurance covers, you can shop for insurance on TTOL sponsor Insure My Trip. If you click on the link here, your cost will be the same, but TTOL gets a small commission.

If you shop for comprehensive plans, they will cover medical bills, including specifically medical evac. You can fill out your details, including age, etc., and what regular travel insurance you need for trip interruption, etc. Look at the prices, and compare coverages, for what is important to YOU. For medical coverages in particular, be aware of whether the coverage is secondary or primary. If secondary, it means that you MIGHT have to pay upfront for those bills and wait to be reimbursed, which might be really difficult, if you have to pay upfront for those bills. As far as medical evac in general, any medical evac from the Caribbean is a MINIMUM of $50,000, so if medical evac coverage is less than $50,000, don't buy that policy. Many of the good ones are $100K or over.

Please post any additional questions.