Sounds like a good plan. We used to do something similar in conjunction with the crossover ceremony at the local Scout camp (which the Cubmaster turned into a parent/son campout.) The Webelos crossed over on Friday night (I attended, along with my ASM, SPL, and ASPL.) The next morning, the 4 of us picked up the newly minted Scouts with their backpacks (we gave them a list of gear ahead of time) and took them on a 4-mile hike around the lake to a remote campsite. We'd usually take about 6 hours to get there, stopping along the way to help them re-pack their packs, lash on sleeping bags better (this was the days of external frame packs), and teach them basic skills like how to hike, how to purify water (plop, plop, fizz, fizz in the days before filters), and spending two hours on a cooked lunch (which doubled as a How to Use a Stove lesson.) Then, in camp, we covered basic camping skills; the next morning, we hiked back to the Cub camp and went home. All the boys had earned a couple of skill awards and gotten started on a couple of merit badge requirements, and found it easier to assimilate into the Troop as a result.

Good luck - it's an idea that really does pay off.