I took out a rookie ship - the Minmatar Reaper - on a tour of the nearby lo-sec systems. I figured that in a ship that's provided absolutely free I would be safe enough (who's going to shoot it?) and not worry about loses.
I christened the ship "Tourist Bus" and started visiting the lo-sec systems in the neighborhood to set up various bookmarks to be used in the future when I have evil intentions. The tour went fine and I continued for several evenings laying out bookmarks for safe spots.
Only once did I get blown up and I'm still not exactly sure what happened... I had warped to within 100k of something (a moon? a base?) and dropped a couple bookmarks on the trip. I was sitting there trying to decide where to go next when POW! WOOT! WOOT! WOOT! RED! RED! RED! and I was in my pod. My guess is that I somehow got too close to a POS (Player Owned Structure) and the defense guns automatically took advantage of my sitting target to blow me up. It did give me a chance to practice the "point at a celestial and spam warp" to get the pod to safety. That seemed to work fine.
So back home in the pod to pick up a new Reaper provided by the friendly insurance company. (In hindsight I could have stopped at any station where I didn't have a ship to get that free one).
Eventually I ended up with multiple safe bookmarks at most of the nearby lo-sec systems. I still need to drop a few more in systems that I haven't visited yet, but it's been a very good start.