Not sure I completely agree with that, but it does depend on the folks involved and communication.
Point in case: We took our 22' sailboat to the San Juans for a week in 2010. Had a ball but it was just DW and me. Didn't meet anyone, pretty much the smallest boat out there, but very relaxing. In early 2013 I posted on a sailing forum and asked if anyone wanted to join us in a small boat flotilla in August. I got about 10 replies and in the end 5 of us showed up. I didn't tell DW until about a month before the trip because I knew she wasn't keen on the drunken raft ups the yacht club gang had. In the time between my question and the trip I made up an itinerary and got buy in from the other sailors. The 4 other boats showed up, two of them with folks we'd never met, we had a wonderful time, and Bill and Sue, whom we'd never met before that week long trip, are now among our best friends. On Day 3, a Sunday, we discovered that our boat had a leak around the depth sounder head; one of the other sailors had a jar of marine putty that slowed the leak enough for us to continue the trip. If it had been 2010 we'd have been forced to return to Anacortes and cancel the vacation.
This year, instead of taking the boats we took the TT's. We met Bill and Sue near Port Angeles, Washington, and spent a week working our way down to Oregon. It was great. Good friends, good food, and good fun. If we'd never gone out on a limb and done a water-borne caravan we'd have totally missed out on great friends and a couple of really good trips.
2012 GMC Sierra 3500 Crew Cab, Long Bed, 4x4 Dually
2010 R-Vision Trail Cruiser 23QBC
2001 Catalina Capri 22 sailboat "Verboten"