Have any man-made objects left the solar system?

Yes. On January 1, 1993 Pioneer 10 was at a distance of 56 AU, Voyager 1 was at 51 AU, and Voyager 2 was at 39 AU. Their distances from the sun increasing by 2.7, 3.7 and 2.7 AU per year. 1 AU is of course the distance from the Earth to the Sun, and Pluto's orbit is at 30 AU or so.

You can follow the progress of the Voyager Interstellar Mission at the JPL web site. Voyager 1 is currently (November 2003) at 90 Astronomical Units or 8.4 billion miles (13.5 billion kilometers) from the sun, with a light travel time of 25.5 hours round trip from earth.

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