Hi, I have lived and taught abroad twice. This time I plan t...

Hi, well that's a tall order! If you cannot fly you are limited to surface travel. The only problem with surface is that most ships / ferries/ trains do not take dogs ( pets ) at all. So Unless you want to drive, you may want to reconsider the "no fly " option a little more. Can the dog be sedated for a short spell? Then of course if you are in the US you can drive through to your destination in Mexico. That does also present it's own challenges, but it gets around the flying aspect. Aside from your mode of transport dilema, most Caribbean islands speak English fairly well already so you mey want to look for teaching a subject such as math , or history , or biology rather than English. The only exceptions: the French Islands.

Having a cat and traveling is just a matter of some initial first steps and then it's easy. I can't love without my pet kids, and so I always bring one with me :) Get your pup ready for international travel with vax, microchip, etc to obtain a pet passport. Right before your trip (10 days max) you can have a certificate issued for their health and carry the docs with you. Most airlines will accept a small dog or cat in cabin, and you just pay for their ticket (can vary in cost, but runs about $100-250 USD). I have imported my cat to Kuwait and Egypt, and they didn't even care. Europe would be a bit more stringent, and I'm sure you will be presenting papers, and proving you have your documents. Check each country to make sure but it's easy.

Mexico has options for you. I live in Oaxaca state and teach here, but (warning) the wages are extremely low. It meets your other requirements, and students are lovely, the campus is beautiful, beaches are gorgeous.