Louisville or Pensacola?

There is no real contest here. Louisville sits on a working river with barges and strong currents, so in summer swimming means a pool or a drive out to a reservoir lake in the countryside.

Pensacola is built around its beaches. Pensacola Beach and the Gulf Islands National Seashore stretch for miles of white sand and clear green water. Perdido Key is quieter, and the sound side suits small children. Just watch the rip-current flags on rough days.

Louisville eats and drinks with more character. Bourbon runs through everything, from the bars on Whiskey Row to the old fashioned. Dishes like the hot brown, burgoo and Benedictine are found almost nowhere else, and NuLu, the Highlands and Butchertown add farm-to-table Southern kitchens.

Pensacola's strength is simpler: oysters, grouper, royal red shrimp and gumbo, eaten in casual places by the water, plus a decent cluster of restaurants and breweries on Palafox Street. Away from the seafood, and especially along the chain-heavy beach strip, there is less to look for.

The two are fairly even here, and each offers two or three good days. What fills those days is different. Louisville's sights are about racing, sport and bourbon: Churchill Downs, the Muhammad Ali Center, the Slugger Museum and the Speed Art Museum, with Old Louisville's Victorian mansions for a walk.

Pensacola's story goes back further and is more colonial. The Spanish and British layers show in the Seville district and around Plaza Ferdinand, alongside the brick bulk of Fort Pickens and the aircraft at the Naval Aviation Museum. If you plan to visit the museum, bring ID.

Neither city is a clubbing destination, and both are about bars. In Louisville that means dive bars and patios along Bardstown Road, bourbon bars in NuLu and the late licences that let a night run on.

Pensacola splits its evenings between the pubs and rooftops on Palafox Street and sand-floored beach bars on the island. It tends to go quiet early outside summer weekends, while Louisville goes wildest around the Derby in spring.

Pensacola gives you more of the outdoors to get into. The national seashore's dunes, salt marsh and maritime forest are good for birdwatching from the bike path. You can paddle in the bay alongside dolphins, and inland the Blackwater River has clear, sandy water for canoeing. Everything is flat, and the summer heat pushes activity into the mornings.

Louisville's outdoors is gentler and more managed. Olmsted's Cherokee and Iroquois parks have wooded hills and loops, the fossil beds at the Falls of the Ohio are a short trip away, and there is woodland hiking in Bernheim Forest. Mammoth Cave is the standout, an outing rather than something in the city itself.

Louisville has the richer hinterland. Bourbon country around Bardstown, Frankfort and Lawrenceburg alone could fill several days of distillery tours. Lexington's thoroughbred farms and Keeneland, Shaker Village and Lincoln's birthplace add variety beyond the whiskey.

From Pensacola, the best outing is Mobile, with its antebellum streets and battleship museum, followed by Fairhope and Fort Morgan. Further east, Destin and Seaside are more beach towns, so once you leave the city the choice is often just another stretch of sand. In both places you need a car.

Both work well with children, in different ways. Louisville's appeal is its attractions: the zoo, several floors of hands-on exhibits at the science centre, roller coasters and slides at Kentucky Kingdom, and the underground ziplines at the Mega Cavern.

Pensacola is a beach vacation first, with calm sound-side shallows for toddlers and condos with kitchens and pools. Planes at the aviation museum and the tunnels at Fort Pickens fill the other days. Families who want theme parks will find Louisville the better fit.

Plan on a car in either city, but Louisville is the easier of the two. Downtown, the waterfront and NuLu can be walked together, and the drives out to Churchill Downs, the Highlands and the parks are short, with mild traffic.

Pensacola spreads further. Palafox Street and the historic district are compact, and a seasonal trolley runs along the beach strip. The island, the naval air station and Perdido Key, though, are linked by highways and bridges, so nearly every outing becomes a drive.

Neither city is a shopping destination, and the souvenirs say most about the difference. In Louisville, people take home bourbon bottles rarely found elsewhere, Derby hats and racing memorabilia, and Bardstown Road has a stretch of vintage, record and antique shops. Pensacola offers boutiques and antiques on Palafox Street, the Saturday market's crafts and plenty of swimwear.

Pensacola tends to be a little easier on the wallet. Seafood and Southern meals are reasonably priced, the aviation museum is free, the seashore costs little, and rooms inland or out of season are cheaper, though the beachfront is expensive in summer.

Louisville's hotels are moderate outside the racing season, and its parks and Old Louisville's streets are free. Daily spending on meals, tips, admissions and getting around soon adds up, though. Avoid Derby week entirely if money matters, as room rates multiply then.

Louisville has the fuller programme. The Kentucky Center hosts a resident orchestra, opera and ballet, and Actors Theatre has a long reputation for staging new American plays. Summer adds concerts and Shakespeare in the parks, and the bars have regular bluegrass and Americana.

Pensacola concentrates its stage life in the restored Saenger Theatre. The symphony, opera, ballet and touring shows all share it, with community theatre and a few bands adding to the calendar. It makes for a pleasant evening out, but it is smaller in scale.

Pensacola is the more restful place to switch off. It has no spa culture as such, but outside the summer peak the quiet stretches of Perdido Key and the island are slow and uncrowded. Louisville's version of unwinding is a porch in the Highlands or a drive through horse country. For a proper spa stay, its visitors need to drive to the old mineral-spring resorts at French Lick and West Baden Springs in southern Indiana.