Our Pack has a tradition of taking our Webelos on adventures that do not include the rest of the Pack. This is a sort of recognition that they are now leaders in our Pack and therefore get more advanced outings.
We have historically alternated between two outings: The Wisconsin Maritime Museum where we sleep on a Submarine in Lake Michigan, and Eagle Cave where we sleep in and explore a cave.
Target a date in Oct/Nov/Dec and start planning in Jan/Feb/Mar to get good dates. Also consider the next year school calendar when planning. We recommend scheduling the Museum on a Saturday night for ease of travel.
This is a one night adventure (best scheduled for a Saturday) where you arrive around 7pm at the museum, then spend the night (until midnight) touring the submarine, pushing buttons, crawling inside torpedo tubes, and then you sleep on the crew bunks. The next morning you get free access to the museum and then leave at your own leisure.
You have to eat dinner before arrival and Manitowoc has quite a few nice places to meet as a group prior to the 7pm arrival time.
This is a two night adventure where you arrive Friday evening and stay in a cave for two nights. Meals are provided (see link). The scouts and adults explore every nook and cranny of this cave. It's such a fun adventure. There is a cafeteria and a trading post (games/snacks/souvenirs).