Purchase airfare and visa NOW for January 2018 trip?

What is difficult about flying to Toronto, Cancun, Mexico City, Nassua, Caymans, Costa Rica, Panama City, and on and on.

I have a near-phobia of big cities. I will go through Havana if I must, but would rather avoid it. Traveling to the DFW airport is stressful enough. My plan B is to make sure my car insurance is paid up, park in Laredo, then fly out of Monterrey, Mexico, changing planes in either Cancun or Mexico City whichever is cheaper. I certainly don't relish the idea of dragging a suitcase full of "regalos" on a bus from Laredo to Monterrey. Mexico is less safe than it was 10 years ago. If I have to spend $1,000 to get there and want to see communism face-to-face, I may as well go to Santa Elena, Venezuela, just across the border from Brazil.

Because flying out of another city for me as opposed directly from JFK to Havana turns into at least a 12 hour ordeal,at least.

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