But even if our aspirations for a night of undomesticated, immoderate revelry were unfulfilled, the two-family trip was a revelation in less dramatic but equally significant ways. As our family’s designated travel planner, for example, I was thrilled to have another set of eyes and interests guiding our itinerary. While I was searching for rentals, Meghan compiled a list of friend-recommended restaurants and made reservations for a three-hour Confederacy of Cruisers “Creole New Orleans” bicycle tour ($49 per adult). It was a two-family outing that wouldn’t have occurred to me. But the two- and three-year-olds rode in toddler seats mounted on each dad’s bike. It ended up being a high point of the trip.

Our guide, Keith, a native New Orleanean in a white linen shirt, a straw hat and a silver beard, performed his hometown’s history with theatrical flourish. In his telling, the complex interwoven narrative of African slaves and freed blacks, of French Canadian “Cajuns” and Colonial Protestants, of German, Italian and Irish immigrants was an artfully constructed dark comedy. The ride itself had us navigating mellow side streets a few blocks at a time, then stopping at a cathedral or a monument or an old recording studio-turned-laundromat, where Keith would fire off anecdotes and trivia, periodically lamenting that he was “again giving unjustifiably short shrift to the Native Americans” — a lighthearted yet self-aware acknowledgment of how much history he was glossing over.

That night we all piled into Meghan and Andrew’s S.U.V. and drove across town. We were following the recommendation of the owner of our rental, Danny, a native New Yorker who has lived down South for decades. Danny had offered to pick Tim, Roxie and me up at the airport and had arrived in a cream-colored, 1980s-era Cadillac with a laundry list of recommendations that he rattled off faster than I could write them down: the not-to-miss live music happening that week, the neighborhood bar that sells crayfish at $10 per pound on Tuesdays and his favorite .50-cent raw oyster happy hour: Superior Seafood in Uptown. I trusted him implicitly.