Trip type
City weekend
Two or three nights. One neighborhood well.
New York, New Orleans, Chicago, Charleston, Old San Juan. Casino-centered weekends — Las Vegas — live under Casinos.
City weekend
New York CityA two- or three-night walk: one borough well, not five badly.
Casino trip
Las VegasStrip spectacle, Sphere, shows, and casino resorts — the flagship casino trip.
City weekend
New OrleansMusic, food, and a river city that still rewards getting lost on purpose.
Coastal city
CharlestonA walkable peninsula, barrier islands, and a food town that is no longer a secret.
Coastal city
Virginia Beach, VAA working Atlantic beach town: boardwalk, pier, and a navy-town downtown you can walk.
City weekend
ChicagoA lake city that still feels like a U.S. downtown: trains, architecture, neighborhoods.
Islands
Puerto RicoA U.S. island trip with no passport for U.S. citizens — Old San Juan, rainforest, and the west coast.