Santa Maria Novella (West).
The first assassination is part of the tutorial in Assassin's Creed 2. You are required to remain Anonymous or else it's total desynchronization and you start over. Regardless of how you approach Uberto, he will spot Ezio and say, "You.." Don't panic and run away. Just assassinate him quickly from the front.
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This is a "variety pack" of assassinations for Francesco de' Pazzi.
A chase is intended for this target. Due to the updated AI in AC2, fleeing targets no longer follow a predetermined path... sort of. This target flees a short distance using a predetermined path, but thereafter it adapts the flight path based on where you are in relation to the next waypoint. We thus have a brief opportunity to do some tricks on this guy.