Deciding when to retire might be the easy part. Deciding where to do it takes a bit of work. There are plenty of lists out there..claiming to have the top ten best. But all those good places have some things in common that you should look for. Free activities, good entertainment like theatre and concerts, an historic atmosphere,plenty of open space and if possible a gentle climate with rare extremes. Make that money last a bit longer. look for communities that give senior citizens a good tax break.