Please consider looking at TTOL sponsor SkyMed. They sell medical evac coverage, back to your home. Most other policies provide coverage to the 'nearest medically appropriate facility', which could be San Juan, or Miami, or elsewhere that is not convenient to your family. Sky Med sells weekly and yearly policies, for frequent travelers. Not cheap, but good coverage, but they JUST do medical evac, not general travel insurance, for trip cancellation, interruption, baggage protection, etc.

For coverage for just a particular trip, or general travel insurance, with medical evac one of the coverages, you can go to TTOL sponsor "Insure My Trip" and compare coverages across many different policies.

For either company, if you use the link here on the sponsors page, it doesn't cost YOU any more, but TTOL gets a small commission.