You can find lots of information and articles on the countries and cities you're interested in retiring to at websites like International Living, Escape Artist and AngloINFO. International Living even offers a short quiz you can take to help you discover your ideal overseas retirement location. There are also some great books on this topic like "How to Retire Overseas: Everything You Need to Know to Live Well (for Less) Abroad" by Kathleen Peddicord, and "Retirement Without Borders" by Barry Golson. These books and others like it are available in book stores nationwide or online atamazon.com. Or, check with your local public library.
Another good tip is to talk or network with some expatriates who have already made the move you're thinking about making. They can give you tips and suggestions, as well as the advantages and disadvantages and day-to-day reality of living in a particular country. Some popular sites to finding expat resources are expatexchange.com and expatforum.com. Here are some other areas you need to investigate.
Cost of living: Retiring abroad used to be seen as a surefire way to live beyond your means, and for some countries it still is. But the U.S. dollar isn't what it used to be, so your money may not stretch as far as you think. See numbeo.com and xpatulator.com for a country-by-country cost of living comparison.
Safety and stability: The U.S. State Department offers background notes or fact sheets on 200 countries providing information about the land, people, history, government, political conditions, economy and foreign relations.
Weather: Use worldclimate.com to get weather information on just about every significant city in the world.
Taxes: No matter what foreign country you decide to retire in, as long as you're a U.S. citizen you still have to pay U.S. taxes. For details see the IRS publication 54, "Tax Guide for U.S. Citizens and Resident Aliens Abroad."
Health care: Medicare does not cover retirees outside the U.S., so you'll need to contact theembassy or consulate of your destination country to see how you can be covered as a foreign resident. Many countries provide government-sponsored health care that's inexpensive, accessible and just as good as what you get in the states, or you may want to buy a policy. Outfits like the Association of Americans Resident Overseas, April Medibroker and Bupa Internationaloffer or broker affordable health plans.
Social Security: This is the one area you don't need to worry about. You can receive your monthly Social Security benefits almost anywhere you live around the world. Your benefits can be deposited into your bank account either in the U.S. or in your new home country - there are some exceptions. To learn more, see ssa.gov/pubs/10137.pdf.
Test run: Once you settle on a destination, be sure you visit multiple times during different seasons to see whether you can envision yourself living there and not just exploring the place as a tourist. If you like what you see but aren't sure where to live, rent before you buy to be certain you're happy with your choice.