Key West or Orange Beach?

Orange Beach has the beach Key West lacks: a long, unbroken run of soft white quartz sand on the Gulf, with low dunes behind it, clear green water on calm days and a gentle slope for wading. Key West's own beaches are small. Smathers is imported sand, Higgs is a local spot by the pier, and Fort Zachary Taylor has clear water over a rocky shore, so most people there spend their water time on boats or snorkelling over the reef.

The calendar turns this around in the cooler months. Key West's sea stays swimmable through winter, while Orange Beach's water turns cold enough that beach days become walks. Orange Beach also has rip currents to watch for, which Key West's reef-sheltered water does not.

Both towns eat casually and mostly from the sea, and neither has much range beyond it. The difference is in the accent. Key West leans towards Cuba, with Cuban sandwiches and café con leche from takeaway windows, conch fritters, stone crab in season and the Key lime pie it argues over.

Orange Beach is Southern Gulf cooking: Royal Red shrimp, raw and chargrilled oysters, West Indies crab salad and big Southern breakfasts, best at the fish houses on the back bays. In both places, plan around a few good seafood dinners rather than a varied week.

Here the two are far apart. Key West's Old Town is one of the largest districts of historic wooden houses in the United States, and its museums are small but full of character: Hemingway's house and six-toed cats, Truman's Little White House, the lighthouse, Audubon House and the wreckers' treasure.

Orange Beach grew from a fishing settlement into a line of condo towers and has only a small local museum. Its history lies outside town, in Pensacola's old quarter, Mobile and Fort Morgan, so anyone who wants sights there has to drive to them.

Key West is the much bigger night out. Duval Street is a long, walkable run of open-air bars and saloons where you carry a drink from one to the next until the small hours, with sunset on Mallory Square as the opening act and an established gay scene at the upper end.

Orange Beach's evenings centre on the Flora-Bama roadhouse at the state line and a few bars around the marina and Perdido Pass. They are lively on summer weekends and in spring break, quiet otherwise, and you need a car or taxi between them. Neither place has real clubs.

The two are about equal, but Key West's outdoors is almost all under water. The coral reef a few kilometres offshore, with turtles and rays, the remote Dry Tortugas and the mangrove flats for tarpon and bonefish are its strengths, and on land the island is flat with little to explore.

Orange Beach mixes land and water. A paved backcountry trail runs through pine woods and wetland past alligator ponds into Gulf State Park, the back bays suit kayaks, and Bon Secour refuge is good for birding during the migrations. Its offshore diving is on artificial reefs rather than living coral.

Orange Beach is much better placed for outings. Pensacola, with its colonial quarter, naval aviation museum and brick forts, is under an hour away, Mobile's antebellum streets and battleship park are just beyond, and Fairhope, Fort Morgan and the ferry to Dauphin Island fill shorter days.

Key West sits at the end of the road. The Dry Tortugas ferry to Fort Jefferson is a memorable exception, and the drive over the Seven Mile Bridge to Marathon's turtle hospital is pleasant, but Miami and the Everglades are too far for a day.

Orange Beach is the far easier family choice. The town runs on condo rentals with pools and kitchens, soft sand and shallow water, and the rest days are covered by dolphin boats, the marina Ferris wheel, mini golf, and a water park and small zoo within half an hour. Keep a close eye on rip currents.

Key West can work for older children who will snorkel the reef, ride the Dry Tortugas ferry and see the butterfly conservatory and Hemingway's cats. Duval Street's drinking and the adult tone of Fantasy Fest mean families do best staying in the quiet residential lanes.

Key West is far simpler. Old Town is compact and flat, the sights, bars and harbour are a short walk from Duval Street, and a rented bike covers the rest, so a car is more of a burden than a help.

Orange Beach is strung out along a single coastal highway with almost no useful public transport. A car is needed for dinners, groceries and every outing, and summer traffic on the main road crawls. Bikes are good only on the trails and side roads.

Neither town is a reason to shop, but they disappoint in different ways. Key West at least has some local character: Old Town galleries with tropical painting and prints, hand-rolled cigars from its cigar-making past and sponge shops by the harbour, alongside the T-shirts on Duval.

Orange Beach sells beachwear and fishing gear along the main road, and its one real draw is the large outlet mall in Foley, a short drive inland, for branded goods at lower prices.

Both are American resorts and neither is cheap, but Key West costs noticeably more. Land is scarce on the island, rooms in conch-house guesthouses and waterfront resorts are dear, and boat trips and the Tortugas ferry add up. You do save on a car, and late summer is the cheapest time.

Orange Beach is easier on the budget, especially for groups sharing a condo with a kitchen. Summer weekends are expensive and a hire car is a fixed cost, but from late autumn to early spring rates fall sharply.

The two are close, and both lean towards bar music. Key West has slightly more beyond it: the nightly street performers at Mallory Square, a long tradition of drag cabaret, the Tennessee Williams Theatre and a winter symphony season.

Orange Beach's strength is bigger touring shows. The marina amphitheatre brings country, rock and pop acts in the warmer months, and every November the Frank Brown International Songwriters' Festival fills the stages around the state line. It has no theatre or classical music.

Neither has a bathing or spa tradition, so the calm comes from the setting. Key West does it a little better: guesthouses around small pools and gardens in the shaded lanes of Old Town, resort spas and easy yoga, and a town that stops for sunset. The bars are never far away, though.

Orange Beach offers empty mornings and sunsets over the back bays, but that quiet really holds only from autumn to spring. Summer weekends and spring break fill it with noise.