Key West or Pensacola?

Pensacola has the far better beaches. Pensacola Beach and the Gulf Islands National Seashore run for miles along Santa Rosa Island, with fine white quartz sand, low dunes and usually gentle surf. Perdido Key and the calm sound side give you quieter options. The catch is the season: in winter the water is too cold to swim, and rip currents need watching.

Key West has the warmer, calmer sea and far less sand. Smathers, Higgs and Fort Zachary Taylor are small, and Fort Zachary Taylor's shore is coral rubble. Days on the water there mean snorkelling and boat trips rather than lying on a towel. The nearest classic sandy beach is at Bahia Honda, about an hour's drive away.

The two eat about equally well, and both lean heavily on seafood. The difference is the influence behind it. Key West cooks with a Cuban accent: Cuban sandwiches and strong coffee from takeaway windows, conch fritters, stone crab in season and the eternal argument over Key lime pie.

Pensacola looks to the Gulf and the Deep South. Expect oysters raw or chargrilled, royal red shrimp, Creole-tinged gumbo, and a downtown cluster of modern Southern restaurants and brewery taprooms around Palafox Street. In both places the best meals are casual waterfront ones, and the busiest tourist strip is the weakest place to eat.

Neither is a big museum destination, and each needs only two or three days. In Key West the town is the sight. Its large district of white conch cottages, Victorian verandas and cigar-era houses is best seen on foot, and the stops along the way are literary and presidential: the Hemingway Home with its six-toed cats and Truman's Little White House.

Pensacola's history is older and more layered, with Spanish, French and British rule still visible in the Seville district and around Plaza Ferdinand. Its single biggest draw, the National Naval Aviation Museum, is larger than anything in Key West. It sits on an active base, though, so expect ID checks.

Key West is the place for a long night out. Duval Street is a continuous run of open-sided bars and rooftop decks where you carry a drink from one to the next until the small hours. The night starts with sunset on Mallory Square, and there is a long-established gay scene at the upper end of the street. It is loud and boozy rather than polished.

Pensacola's evenings are smaller and more local: pubs, cocktail bars and taprooms on Palafox Street and in Seville Quarter, plus sand-floored beach bars in summer. Neither has much club life, but outside weekends and the summer peak Pensacola winds down early.

Both are flat, watery places that are equally good for outdoor time, but the water means different things. From Key West, boats run out to a living coral reef for snorkelling with rays and turtles. Ferries and seaplanes reach the Dry Tortugas, and the mangrove flats are prized for fly-fishing and paddling.

Pensacola has more to do on land. The national seashore has dunes, salt marsh and a bike path with herons, ospreys and dolphins in the sound. Inland, the clear Blackwater River is good for canoeing and tubing. Its diving is on a sunken aircraft carrier rather than a natural reef.

Pensacola has more within easy reach. Mobile is about an hour west, with antebellum streets, deep Mardi Gras roots and a battleship museum. Across the bay are Fairhope and Fort Morgan, and to the east are Destin, Seaside and Rosemary Beach, all with a car.

Key West sits at the end of the road, and its one great outing is by sea: Fort Jefferson in the Dry Tortugas. Beyond that, the Overseas Highway leads to Marathon and Islamorada over the Seven Mile Bridge, and Miami is too far for a comfortable day.

Pensacola is the easier family base. It has warm, gentle summer water, shallow sound-side spots for toddlers, condos with kitchens and pools, and rainy-day options that children enjoy: planes at the aviation museum, the Blue Angels, a zoo and the lighthouse climb. Just don't expect theme parks.

Key West can work for older children who love snorkelling and boats. The Dry Tortugas ferry and the butterfly conservatory are both highlights. But Duval Street's drinking is hard to avoid in such a small town, and family-sized lodging costs more.

This is where the two differ most. Key West's Old Town is flat and compact, so a bicycle or your own feet get you to almost everything, and a car is more nuisance than help.

Pensacola is spread out. Downtown, the beach, the naval air station and Perdido Key are separated by highways and bridges. Apart from a seasonal beach trolley and infrequent buses, you will be driving almost everywhere, so budget for a hire car from the start.

Neither is worth the trip for shopping. Key West's better finds are its Old Town art galleries, hand-rolled cigars and the sponge and shell shops by the harbour, among Duval Street's T-shirts.

Pensacola has independent boutiques, antique shops and a Saturday market on Palafox. It also has a regional mall inland, which Key West lacks, if you need the usual chain stores.

Pensacola is clearly the cheaper trip. Rooms in town and inland cost much less than beachfront ones, prices fall sharply out of season, seafood meals are fairly priced, and both the aviation museum and the seashore are cheap or free. The cost people forget is the car.

Key West is one of the more expensive places to stay in the country. Its limited land pushes up room prices, and boat trips and the Dry Tortugas ferry add up fast. Walking, cycling, the free sunset and Cuban takeaway help, and late summer is the least expensive season.

Both are modest, but in different ways. Key West's performances are informal and outdoors: songwriters and cover bands in the open-air bars every night, long-running drag cabaret, and the jugglers and musicians of the Mallory Square sunset.

Pensacola has the more traditional stage. The restored 1925 Saenger Theatre hosts a symphony, an opera company, ballet and touring shows. That makes it better for a formal night out, though Key West has more casual live music.

Key West does slow living somewhat better. Guesthouses are built around small pools and tropical gardens, the quiet lanes of Old Town are a short walk from Duval Street, and the whole town stops for sunset. Spas, massage and yoga are easy to find.

Pensacola offers hotel day spas and town massage studios. Its calm comes mostly from the empty beaches of Perdido Key and the island outside the summer peak. Neither has any tradition of thermal baths.