Clearwater or Louisville?

This is where the two cities are furthest apart. Clearwater Beach is long, powder-white and gently shelving, and the water stays warm for months on end. If the main beach is too busy, there is quieter sand on Sand Key and Caladesi Island.

Louisville has no beach of any kind. The Ohio is a barge river with strong currents, so swimming means a pool, or a drive out to the reservoir lakes in the Kentucky countryside.

Louisville eats and drinks with more character. Bourbon runs through everything, from the Whiskey Row bars to the distillery tasting rooms, and the hot brown, Benedictine and Derby pie are dishes you won't find elsewhere. NuLu, the Highlands and Butchertown hold the better kitchens.

Clearwater's food is simpler: fried or blackened grouper, stone crab in season and shrimp baskets at dockside shacks, with chain grills taking up much of the beachfront. Its best meal out is in the Greek tavernas of Tarpon Springs.

Louisville has a real set of sights, while Clearwater has very little. Churchill Downs and the Derby Museum, the Muhammad Ali Center, the Slugger and Frazier museums on Whiskey Row and the Victorian streets of Old Louisville make two or three full days.

Clearwater has a few early twentieth-century buildings downtown and a restored 1920s theatre, but nothing to plan a day around. That is why its visitors drive to St Petersburg or Tampa for museums.

Neither is a clubbing city, but Louisville gives you more reasons to go out. There are dive bars and patios all along Bardstown Road and bourbon and cocktail bars in NuLu, and with late licences a night can run on. Derby week brings the whole city out.

In Clearwater the evening starts, and mostly ends, with the sunset at Pier 60, followed by tiki decks and cover bands. Only in spring does the beach stay loud. For the rest of the year, a proper night out means going to Ybor City in Tampa.

The two are broadly level here, but the settings could hardly be less alike. Clearwater's outdoors are flat and watery: mangrove channels to kayak, dolphins in the harbour, manatees in winter, ospreys on Caladesi Island and the Pinellas Trail for easy cycling.

Louisville offers woods and hills instead of water. It has Olmsted's wooded parks, fossil beds at the Falls of the Ohio and forest hiking at Bernheim and Jefferson Memorial Forest, and Mammoth Cave is within reach for a long day.

Both cities rely on what lies around them, and from both you need a car. Clearwater's outings are urban and cultural: the Dalí Museum in St Petersburg, Ybor City in Tampa, the Ringling in Sarasota and the Greek harbour at Tarpon Springs. Orlando's theme parks are about two hours away.

Louisville's outings are rural. There are distillery tours around Bardstown and Frankfort, Lexington's thoroughbred farms and Keeneland racecourse, Shaker Village and Lincoln's birthplace. If you're touring distilleries, plan a designated driver.

Clearwater is the easier vacation with children, mainly because of the sea. The water is calm, shallow and almost without surf, so small children can paddle safely, and the lifeguards and playground at Pier 60 keep the beach days simple. The rescued dolphins and turtles at the Clearwater Marine Aquarium and the pirate boat trips fill the gaps, and condos with kitchens make the days more relaxed.

Louisville has plenty for children too. Kentucky Kingdom's roller coasters and water park can fill a whole summer day, and there is a good zoo, the Kentucky Science Center and the underground ziplines of the Mega Cavern. What it can't offer is an easy beach day on the doorstep, and its attractions are spread across town, so each outing means getting the family into the car.

Both are car country, with slow buses and no rail. The difference is in what you can do on foot. On Clearwater Beach, hotels, restaurants and the sand sit close together, a trolley runs to Sand Key and a ferry goes downtown, but the causeway backs up on busy weekends.

In Louisville, Main Street, the waterfront and NuLu are walkable. Churchill Downs, the Highlands and the parks need a car or ride-hailing, but at least the traffic is light.

Neither city is a shopping destination, but Louisville has a little more to browse. NuLu's design shops and galleries and Bardstown Road's vintage clothing, records and antiques beat Clearwater's beachwear and souvenir strip, and a bottle of Kentucky bourbon that's hard to find elsewhere makes the best souvenir. In Clearwater, the most local thing to buy is a natural sponge from Tarpon Springs.

Costs are similar in the two cities, and in both, timing matters more than anything else. Clearwater's beachfront rooms are dearest in the late winter and spring peak and cheaper in the hot, stormy summer. Free beaches and condo kitchens help families keep costs down.

Louisville's hotels are moderately priced outside racing season, but a hire car or ride-hailing adds to the bill every day, and in Derby week room rates go up several times over. Both cities are at their most expensive in spring.

Louisville has the fuller programme. The Kentucky Center is home to the city's orchestra, opera and ballet, and Actors Theatre is known for staging new American plays. Summer brings Shakespeare in Central Park and concerts at the Iroquois Amphitheater, and the bars have bluegrass and Americana.

Clearwater relies on touring acts at Ruth Eckerd Hall and smaller shows at the 1920s Capitol Theatre. For opera and ballet, you have to go to Tampa.

Clearwater is the more restful place, though not because of its spas: in both cities those are hotel treatment rooms and day spas. What makes it restful is a slow routine of pools, balconies, long lunches and evenings by the marina that asks nothing of you.

In Louisville, unwinding means an afternoon on a porch in the Highlands or a drive through horse country. For a real spa break, the old mineral-spring resorts of French Lick and West Baden Springs in southern Indiana are about an hour and a half away.