Naples, Florida or Pensacola?

Both are excellent beach towns on the Gulf, and the difference lies in where and how you swim. In Naples the sand runs along the city itself, so a stay in Old Naples means walking down a side street to the water, with the pier as a meeting point and the wilder stretches at Barefoot Beach and Delnor-Wiggins Pass to the north. The water is calm and stays warm enough to wade into in winter, though algae blooms and stingrays in the shallows are occasional nuisances.

Pensacola's beaches lie across the bay on Santa Rosa Island, a short drive over the bridges from downtown. The reward is some of the whitest quartz sand on the coast and long protected dunes in the national seashore, plus calm sound-side water for toddlers. Rip currents on rough days demand more care than in Naples, and the swimming season is limited to summer.

Both cities eat well on Gulf seafood without being food destinations, but the mood is different. Naples leans formal, with white-tablecloth dining rooms and wine bars along Fifth Avenue South and stone crab claws in the cooler months, best for a long, polished dinner.

Pensacola is more casual and more Southern: raw and chargrilled oysters, royal red shrimp and gumbo with a Creole touch at waterfront places on the bay, plus craft breweries and brunch spots around Palafox Street and a Saturday market for local produce.

Pensacola has much more history to explore. As the City of Five Flags it has restored colonial and Victorian houses around the Seville district and Plaza Ferdinand, the brick Fort Pickens on the tip of Santa Rosa Island, and the vast National Naval Aviation Museum with its historic aircraft, enough for two or three days.

Naples is a young resort town with a day's worth of sights at most. The Baker Museum's modern and American art and the Revs Institute's historic cars are worthwhile, especially for car enthusiasts, and Palm Cottage gives a glimpse of early Naples, but most visitors spend their time outdoors.

Pensacola is the livelier of the two after dark. Palafox Street and the Seville Quarter fill with pubs, rooftop terraces and taprooms on weekend nights, the island's sand-floored beach bars take on a party feel in summer, and the rowdy roadhouse on the Alabama line at Perdido Key is a local institution.

Naples barely has a night scene. Evenings mean a sunset drink, dinner and perhaps a piano lounge on Fifth Avenue South, with an older crowd and a town that is quiet well before midnight. Neither has much in the way of clubs.

Both are flat, watery landscapes with plenty to do outdoors, but Naples borders true wilderness. Big Cypress, the western Everglades, the Corkscrew Swamp boardwalk and the mangrove channels of the Ten Thousand Islands offer alligators, wading birds and some of the best kayaking in Florida, at its best in the dry winter.

Pensacola's outdoors are coastal and gentler: dunes, salt marsh and maritime forest along the national seashore's bike path, dolphins in the sound and canoeing or tubing on the clear Blackwater River inland. It also has something Naples lacks, a sunken aircraft carrier offshore that draws experienced divers.

Neither city is a great base for excursions, and both need a car for every outing. From Naples the best choices are the Edison and Ford Winter Estates in Fort Myers and the shelling islands of Sanibel and Captiva, with Miami a long day across the Everglades.

Pensacola has the more characterful single trip in Mobile, with its antebellum streets and Mardi Gras heritage, plus Fairhope across the bay. Heading east, the outings are mostly other beach towns such as Destin, Seaside and Rosemary Beach.

Both work well for a beach vacation with children, and neither has a theme park within easy reach. Naples offers warm, calm water even in the cooler months, a zoo with a boat ride past primate islands and a children's museum aimed at the under-tens.

Pensacola gives children planes and forts: the naval aviation museum, the home base of the Blue Angels, the lighthouse climb and the tunnels of Fort Pickens. Its condos with kitchens and pools also suit families settling in for a week.

Both are car towns with thin bus networks, so a rental is part of the plan in either. Naples has the edge in one respect: stay in the walkable grid of Old Naples and the beach, restaurants and shops are all on foot.

In Pensacola the walkable downtown around Palafox Street is separated from the beach by the bay and its bridges, so most stays involve driving between the two, though a free trolley runs along the beach strip in season.

Naples is the better place to browse. Fifth Avenue South and Third Street South line up galleries, jewellers and resort-wear boutiques under the palms, an open-air luxury mall gathers the designer labels, and Tin City's old clam-shelling sheds add souvenirs.

Pensacola's offer is small: some independent boutiques and antique shops on Palafox Street, a Saturday market with local crafts and a standard regional mall. It is fine for an afternoon, not a reason to go.

Pensacola costs noticeably less. Rooms in town are cheaper than on the island, casual seafood is reasonably priced, the naval aviation museum is free, and outside summer the beach hotels drop their rates sharply.

Naples is expensive, and its high season from roughly January to April falls exactly when its weather is best. Summer brings bargains but also heat and storms. In both, car hire is an unavoidable extra.

For small cities, both have a fuller stage than you might expect, and the difference is in the setting. Naples centres on its arts campus, where the Naples Philharmonic plays in its own hall alongside touring Broadway shows, though the programme is concentrated in the winter season.

Pensacola's hub is the restored 1925 Saenger Theatre downtown, home to the local symphony, opera and ballet, a handsome historic venue for a regional evening out.

Naples is the more restful choice. Its big beachfront resorts run large spas with pools and fitness classes open to visitors, there is golf in abundance, and the whole town moves at an unwinding pace.

Pensacola offers day spas in the larger beach hotels and massage studios in town, but little more. Its calm comes from the quiet stretches of Perdido Key and the island outside the summer peak.