Florida Keys or Hilton Head?

Hilton Head has the better beaches. Its Atlantic shore is one wide strand of firm sand with gentle surf, from busy Coligny to quieter Folly Field, and it is a place to set down a towel for the whole day. The price is greenish, tidal water and a swimming season limited to the warmer months.

The Keys have the warmer sea but little sand to go with it. Much of the shore is mangrove, rock and seagrass flats, so beach days centre on Bahia Honda, Sombrero Beach or Fort Zachary Taylor, and most of the swimming happens from a boat or a dock.

Both are places for seafood eaten on a deck by the water, but the Keys have the more distinctive food. Yellowtail snapper and hogfish caught that morning, stone crab claws, conch fritters and Key lime pie come with a real Cuban side in Key West, from café con leche to bakery windows, as well as a few serious dining rooms in Old Town.

Hilton Head's answer is Lowcountry cooking: shrimp and grits, she-crab soup, Lowcountry boils and May River oysters at cool-weather roasts. Beyond that, its resort grills and brunch spots are pleasant rather than memorable, and Old Town Bluffton is the more local option.

Key West gives the Keys a clear lead here. Old Town's conch houses and Victorian porches, the Hemingway Home, the Truman Little White House and the boat out to Fort Jefferson in the Dry Tortugas fill a satisfying couple of days.

Hilton Head's history is smaller in scale but serious. The Gullah story is told at Mitchelville Freedom Park and in the old family neighbourhoods, alongside plantation ruins and a Civil War earthwork. For historic streets, though, visitors drive to Savannah or Beaufort.

After dark there is no contest. Key West's evening starts with the sunset crowd at Mallory Square and runs late along Duval Street, through open-sided bars, rooftop decks and live bands, with a long-established gay scene and drag cabaret at the lower end. Clubs are rare, so plan on bar-hopping.

Hilton Head goes to bed early. A few waterfront bars around Coligny and the marinas fill up on summer nights with a cover band, but the crowd is mostly families and golfers, and by midnight the island is quiet.

The Keys have the bigger draw outdoors, and nearly all of it is on the water. There is the reef at John Pennekamp and Looe Key, wreck dives off Key Largo, the Dry Tortugas, and the backcountry flats around Islamorada for bonefish and tarpon. Much of the coral is patchy, but the sea life makes a snorkel worthwhile.

Hilton Head's nature is gentler and starts at the doorstep. Dolphins feed close to shore in Calibogue Sound, kayaks slip through the spartina marsh, and Pinckney Island has herons and alligators. The paved paths under live oaks make cycling the natural way to explore.

Hilton Head is far better placed for days away. Savannah's oak-shaded squares are about 45 minutes off, Beaufort's antebellum port is under an hour north, and Daufuskie Island is a short ferry ride. Charleston makes a long but rewarding day.

In the Keys the day out is mostly the drive itself, down the Overseas Highway through towns that look much alike. The real escapes are the boat from Key West to the Dry Tortugas and, from the Upper Keys, Miami's Art Deco district and Little Havana, about an hour and a half away.

Hilton Head was largely built for this kind of trip. Gentle surf, car-free bike paths, rental houses with kitchens, the playground by the Harbour Town lighthouse and crabbing off docks make for safe, easy days, even without a zoo or theme park.

The Keys work for families mainly in the Middle and Upper Keys. There, Marathon's sea turtle hospital, the dolphin centres and the glass-bottom boats at John Pennekamp are real treats for children. Long drives, few sandy beaches and the drinking culture of Key West make it harder going.

Both rely on a car and a single road, but on a very different scale. In the Keys that road is the Overseas Highway, about 180km of bridges. A weekend jam or a hold-up on one bridge can stall the whole chain, and you need the car to see more than one island. Key West's flat, compact Old Town is the walkable exception.

Hilton Head is small enough that once you arrive the car can mostly stay parked. Its bike paths link the beaches, shops and villas, though gated communities such as Sea Pines add entry checks for drivers.

Neither is a place to go shopping, and the difference is mostly in flavour. Key West's Duval Street runs to T-shirts, hand-rolled cigars, hot sauce and Key lime products, with galleries and sea-glass jewellery in the Old Town side streets. Hilton Head has neat open-air shopping villages at Coligny, Shelter Cove and Harbour Town, Gullah sweetgrass baskets to take home, and outlet malls in Bluffton for a rainy day.

Neither is cheap, but Hilton Head is easier on the wallet. Sharing a rental house and cooking, staying in Bluffton or coming in spring or autumn all bring costs down noticeably.

The Keys are among the most expensive places to stay in the country in winter. Almost everything arrives by truck down one road, and charters, dives and waterfront dinners are all priced high. Marathon, the Lower Keys and the summer months help a little, but there is no budget version of the trip.

Live performance in the Keys mostly means music in a bar. In Key West it plays along Duval Street from early afternoon until late, with singer-songwriters, island-style acoustic sets, cover bands and drag cabaret. The Tennessee Williams Theatre and a local symphony add a short winter season of plays and concerts.

Hilton Head is better for a seated evening out. The Arts Center of Coastal Carolina puts on professional theatre and Broadway-style musicals for much of the year, and the island's orchestra plays through the winter. A jazz festival and a Gullah celebration of music, storytelling and dance complete the calendar. Neither place is worth the trip for opera or serious concert-going.

Both restore people through a slower pace rather than a bathing tradition, and both have good resort spas. In the Keys the calm comes from the water: a cottage on a quiet Middle or Lower Key, days built around boats and sunsets, and the spas on private islands near Islamorada, with livelier Key West best kept for early mornings.

Hilton Head's calm is on land, with beach walks, bike rides under live oaks and evenings by the marsh. The island is at its quietest out of season, and it has spas and yoga studios spread across it.