Pensacola or St. Louis?

This is the widest gap between the two. Pensacola Beach and the Gulf Islands National Seashore run for miles of white quartz sand and clear green water about twenty minutes from downtown, with calm, shallow sound-side spots for small children and quieter Perdido Key to the west.

St. Louis has nothing comparable. Its great rivers are working waterways with dangerous currents, and in summer the only way to cool off is a pool or a long drive to an Ozark reservoir.

Pensacola eats well in one key: Gulf seafood, from chargrilled oysters and royal red shrimp to grouper sandwiches, best at casual places on the water. Palafox Street adds modern Southern cooking and breweries, but variety beyond that is thin.

St. Louis offers more range and more character. It has its own local dishes such as toasted ravioli, Provel-topped pizza and gooey butter cake, serious barbecue ribs, Italian trattorias on the Hill and Bosnian, Vietnamese and Ethiopian cooking along South Grand, all with a long brewing tradition behind them.

Pensacola's appeal is its layered colonial past under five flags, seen in the restored houses around Plaza Ferdinand, the brick bulk of Fort Pickens and the vast naval aviation museum, though access to the air station involves ID checks.

St. Louis offers more to see and of greater weight. The Gateway Arch and its museum of westward expansion, the Old Courthouse of the Dred Scott case, the free Saint Louis Art Museum in Forest Park, the mosaics of the Cathedral Basilica and Louis Sullivan's Wainwright Building make up a stronger set of sights.

Neither city is a nightlife destination, and both go quiet early outside weekends and their busy seasons. The difference is in shape: Pensacola keeps its evenings in one walkable pocket of pubs and rooftop bars on Palafox Street and the Seville Quarter, plus sandy beach bars on the island in summer.

St. Louis spreads out across blues taverns in Soulard, dance bars on Washington Avenue, the late-night LGBTQ+ strip in the Grove and student bars on the Loop, so there is more variety but you will need taxis between them.

Pensacola has the richer natural setting for a visitor, all of it flat and watery. Dunes, sea oats and salt marsh on the national seashore, ospreys and nesting shorebirds, dolphins in the sound, a sunken aircraft carrier for divers and clear Blackwater River canoeing make for full days outside.

St. Louis offers greener but quieter pleasures: the large woods and lakes of Forest Park, bluff trails and caves in the Ozark foothills within an hour, cycling on the Katy Trail and wintering bald eagles near Alton.

From Pensacola the best outing is Mobile, with its antebellum streets and battleship museum, followed by Fairhope and Fort Morgan. Heading east, the options are mostly more beach towns such as Destin and Seaside.

St. Louis has the more varied list. Cahokia Mounds, a UNESCO-listed pre-Columbian city, is only twenty minutes away, and French colonial Ste. Genevieve, the German wine towns of Hermann and Augusta, Twain's Hannibal and Lincoln's Springfield add history of real depth. Both need a car.

Pensacola works as a straightforward beach vacation with children: warm, gentle water, condos with kitchens and pools, plus the aircraft museum, the Blue Angels and the lighthouse climb for days off the sand. There are no big attractions or theme parks, though.

St. Louis gives families more to do. The City Museum's climbable maze of tunnels and slides is a highlight for all ages, and the free zoo and Science Center in Forest Park, the Magic House, a nearby theme park and baseball evenings fill a week with ease.

Both cities expect you to drive, but St. Louis gives you a little more help. Its MetroLink light rail links the airport, the Central West End, Forest Park, downtown and the stadium, and parking is easy and roads clear.

In Pensacola, only the compact downtown and a seasonal beach trolley work without a car. The island, the naval air station and Perdido Key are spread far apart along bridges and highways.

Shopping is a sideline in both, though St. Louis gives a slightly better afternoon of browsing. Cherokee Street's vintage, record and antique shops, the Loop's independents and the Central West End's boutiques have more character than Pensacola's few Palafox Street boutiques, regional mall and beach souvenir stands.

Costs come out much the same, and in both a hire car is a cost many visitors forget. In Pensacola the bill depends heavily on the season, since beachfront rooms are dear in summer and drop sharply in the off months.

St. Louis is steadier through the year, with hotels well below coastal-city levels. Free entry to the zoo and Forest Park's museums, cheap barbecue and Bosnian grills help keep daily spending down.

St. Louis is far stronger here. One of the oldest orchestras in the country plays in Powell Hall, Broadway tours fill the Fabulous Fox, the Muny stages summer musicals outdoors in Forest Park and an acclaimed opera festival runs in early summer.

Add the city's blues heritage, from Chuck Berry to the National Blues Museum and the bars of Soulard, and it outclasses Pensacola. There, the restored Saenger Theatre and a community theatre give a pleasant regional night out.

Neither has a spa tradition, so the difference comes down to setting. Pensacola wins on calm: out of season, empty stretches of the island and Perdido Key are easy places to switch off by the sea.

St. Louis offers hotel spas and yoga studios in Clayton and the Central West End, and its most restful hours are slow mornings in Forest Park or the Japanese garden at the Missouri Botanical Garden.