Charleston or Naples, Florida?

Both cities have real beaches, but in Naples they are better and right on the doorstep. Fine, pale sand runs the length of the city, with paths down to it from the ends of Old Naples streets. The Gulf is usually calm, shallow and clear, and in the evening people gather to watch the sun set over the water. Further north, Clam Pass and the dunes of Barefoot Beach feel wilder.

Charleston's beaches are on barrier islands about half an hour out, and each has its own character: surfy Folly Beach, quiet Sullivan's Island with its old forts, and the wider, more resort-like Isle of Palms. The Atlantic there is greener and churned by tides, with rip currents on some days, and in winter it is too cool to swim.

Charleston is the stronger place to eat by some distance. Its Lowcountry cooking includes shrimp and grits, she-crab soup, Carolina Gold rice and winter oyster roasts, and it has deep Gullah Geechee and West African roots. You can eat it in dining rooms in restored townhouses or at barbecue joints that smoke whole hogs, and biscuit breakfasts and craft breweries add to it.

Naples eats comfortably rather than memorably. Steak, Italian and modern American cooking fill Fifth Avenue South, and the local highlight is Gulf grouper and stone crab at the dockside fish houses around Tin City. Neither city has much street food or cheap international cooking.

Charleston has far more to see. The historic peninsula is the main sight, with Rainbow Row, the Battery and the single houses south of Broad Street. Its house museums, Fort Sumter and the International African American Museum deal openly with a hard history, and two or three days covers it well.

Naples is a young resort city with a day's sightseeing at most. There is modern and American art at the Baker Museum, historic racing cars at the Revs Institute for enthusiasts, and Palm Cottage for a glimpse of early Naples. Most visitors spend their time outdoors instead.

Neither city is worth choosing for its nightlife, but Charleston at least has a bar scene. Upper King Street fills with rooftop bars, cocktail rooms and oyster bars, loud with students and weekend groups, and the French Quarter has quieter wine bars and old taverns.

Naples winds down after dinner and a sunset drink. Fifth Avenue South has piano lounges and wine bars that are busy in winter, but the crowd is older and the town is mostly quiet before midnight. For a real night out, people drive to Fort Myers Beach.

Charleston's outdoors is gentle marsh country, while Naples has a true wilderness within reach. Around Charleston, the Lowcountry is spartina marsh, tidal creeks and maritime forest of live oaks hung with Spanish moss. It is best seen from a kayak, often with dolphins alongside, and the Francis Marion National Forest and the ACE Basin add quiet trails and alligators. Spring and autumn are the seasons for it.

From Naples, Big Cypress, the western Everglades, the Corkscrew Swamp boardwalk and the orchids of the Fakahatchee Strand are all within an hour, with wading birds, alligators and, with luck, manatees. Paddling the mangrove channels of the Ten Thousand Islands and Rookery Bay is the outstanding day out, best in the dry winter before summer storms and mosquitoes arrive.

Charleston has the better outings. Middleton Place, Magnolia and Drayton Hall are about half an hour away and pair formal gardens with the history of the enslaved people who worked them. Savannah's squares make a full day two hours south, and Beaufort offers Gullah culture on the sea islands.

The trips from Naples are pleasant but thinner. There are the Edison and Ford Winter Estates in Fort Myers and shelling on Sanibel and Captiva, while the Ringling museums in Sarasota and the city of Miami are each about two hours away. You need a car for all of these from either city.

Both are calm, easy places to take children, and the difference is in the kind of day. Naples is built around the shallow, warm Gulf, where children can collect shells and watch dolphins from the shore. Naples Zoo has a boat ride past primate islands, and the Golisano Children's Museum is aimed at the under-tens.

Charleston mixes beach days with history children can climb on, such as the aircraft carrier at Patriots Point, plus the boat out to Fort Sumter and the South Carolina Aquarium on the waterfront. Neither city has a theme park, and summer afternoons are draining in both.

Once you leave the centre, both are car towns, but in Charleston the centre holds much more of what you came for. Most sights on the flat historic peninsula are within about 3km, and pedicabs and a free shuttle bus fill the gaps, so you can spend days there without driving.

In Naples, the walkable part is the small grid of Old Naples around Fifth Avenue South and the pier. To reach anything else, from the northern beaches to the Everglades, you face long, wide roads, a thin bus network and winter traffic.

Charleston edges ahead for browsing. King Street changes along its length, from antiques dealers on lower King to independent boutiques and design shops further up. In the City Market, Gullah artisans weave sweetgrass baskets, a local craft Naples has nothing to match.

Shopping in Naples is more polished but narrower. Fifth Avenue South and Third Street South have resort wear, jewellers and galleries, and an open-air mall gathers international designer names, a luxury tier Charleston lacks. There are also outlet malls half an hour north.

Neither city is cheap, but Naples costs more. Its beachfront resorts charge premium rates from roughly January to April, its restaurants are priced for a wealthy crowd, and you almost always need a rental car. Summer there is much cheaper, though hot and stormy.

Charleston's inns on the peninsula and its well-known restaurants are pricey too, especially on spring and autumn weekends, but you can see the old town on foot without paying for a car. In both cities the beaches are free, and staying in Mount Pleasant or out in Fort Myers saves money but means driving in every day.

The two are close, and the difference is mostly in timing. Charleston's high point is Spoleto Festival USA in late spring, more than two weeks of opera, chamber music, dance, theatre and jazz. The Dock Street Theatre and the Gaillard Center keep going the rest of the year, and Gullah storytelling and song add a local strand.

Naples has no single big festival. Instead it has a steady season from late autumn to spring, led by the Naples Philharmonic in its own hall, with touring Broadway shows and two theatre companies. In summer it falls almost silent.

Charleston unwinds in town. Its calm comes from shaded walled gardens, quiet church courtyards, porches and long evenings by the water at White Point Garden, and for a proper treatment day you drive out to the resort spas on Kiawah Island.

Naples puts its spas beside the sand. The large beachfront resorts open their pools, treatment rooms and fitness classes to non-guests, and the rest of the slow pace is golf and sunset walks along the Gulf. Thermal springs or a bathing culture are missing from both.