Clearwater or Key West?

Clearwater wins this easily. Its beach is a long strip of powder-white sand where you can wade far out into calm Gulf water. Sand Key, Caladesi and Honeymoon Island offer quieter sand nearby.

In Key West the appeal is warmer, reef-sheltered water rather than the shore. Smathers is imported sand, Fort Zachary Taylor is coral rubble, and seagrass and seaweed make the island better for snorkelling than for wading. A proper beach day there means driving an hour to Bahia Honda.

Both cities eat casually from the sea, and you will find grouper and stone crab in each. Key West has the stronger character thanks to its Cuban side: café con leche and Cuban sandwiches from takeaway windows, conch fritters and the endless argument over Key lime pie. Its best meals are in the fish shacks around the Historic Seaport and Bahama Village.

Clearwater's beachfront relies on chains and tourist grills. A grouper sandwich and a sunset drink are the highlights, and better cooking means an outing to the Greek tavernas of Tarpon Springs or across the bay.

Key West has far more to see. The wooden conch houses and Victorian mansions of Old Town are a sight in themselves. The Hemingway Home, Truman's Little White House and the shipwreck collections fill a couple of days on foot.

Clearwater has a restored 1920s theatre and a few old buildings downtown, but nothing to plan a day around. For its culture you drive to St Petersburg or Tampa.

Key West is the place for a late night. The sunset crowd on Mallory Square moves on to Duval Street, where you carry a drink from one open-sided bar to the next until the small hours, and there is a long-established gay scene at the upper end. The tone is loud and loose rather than stylish, and there are few real clubs.

Clearwater's evenings also start at sunset, around Pier 60, but then settle into tiki decks, cover bands and an early night. Spring is the only time it gets louder, and a proper night out means going to Ybor City in Tampa.

Both are flat, watery places where nearly everything happens from a boat or a paddleboard. Key West has the edge for what lies under the surface: the Florida Reef a few kilometres offshore, tarpon and bonefish on the backcountry flats, and the remote Dry Tortugas with their clear water and birdlife.

Clearwater's wildlife is gentler: dolphins in the harbour, manatees in winter and ospreys in the state parks. It also has something Key West lacks on land, the Pinellas Trail for long, easy bike rides.

Clearwater is far better placed. The Dalí Museum in St Petersburg, Ybor City in Tampa, the Greek sponge docks of Tarpon Springs and Sarasota's Ringling Museum are all within about an hour. Orlando's theme parks are around two hours away, and a car makes all of it easier.

Key West sits at the end of the road. The ferry to Fort Jefferson in the Dry Tortugas is a memorable day out, and the drive over the Seven Mile Bridge to Marathon is worth doing. Miami and the Everglades, though, are too far for a comfortable return.

Clearwater is much the easier base with children. Dolphin-watching cruises and pirate-themed boat trips leave from the marina, and Tampa's Adventure Island water park and the Florida Aquarium are good days out when the beach palls. Hotels are geared to families and have their own pools. You will need a car for almost every outing, though, and in summer the heat and afternoon storms mean doing most things in the morning.

Key West has fewer things for children, and they are mostly on the water: the calm shallows at Fort Zachary Taylor, glass-bottom boat trips over the reef, plus the butterfly conservatory, the shipwreck museum and the trolley tours. The island is not built around families, and its loud drinking side is never far away. Families do best staying on Old Town's quiet residential streets, where getting about by bike is easy.

Key West is far easier without a car. Old Town is compact and flat, nearly everything lies close to Duval Street, and a rented bike is the local way to get about. You only need wheels to explore the wider Keys.

In Clearwater you can walk the beach strip and take the trolley to Sand Key, but beyond the island lies sprawl and the buses are slow. Almost every outing needs a car, and the causeway backs up on busy weekends.

Neither is a shopping destination, and both rely on souvenir shops. In Key West, Old Town's art galleries and hand-rolled cigars make browsing a pleasant part of an evening walk.

Clearwater's extras are more practical: malls and big-box stores on the mainland, natural sponges from Tarpon Springs, and Tampa within reach for department stores and luxury brands.

Clearwater is the cheaper of the two, though still not a bargain. Beachfront rooms cost the most, so staying in a mainland motel or a rental further down the coast saves a good deal. The beaches cost nothing except parking, and summer and autumn bring lower rates for anyone who can take the heat.

Key West is expensive almost everywhere you look. There is little land and strict limits on building, so even a guesthouse in an old conch house is dear, and boat trips, diving and the Dry Tortugas ferry add up quickly. Fish shacks, Cuban takeaway windows and the free sunset on Mallory Square help, and you can walk or cycle instead of paying for a car.

Clearwater's evenings out happen in proper halls. Ruth Eckerd Hall brings in touring bands, comedians, Broadway tours and orchestral concerts, and the restored 1920s Capitol Theatre puts on smaller shows. For opera or ballet you drive to Tampa.

Key West's performers are mostly in the street and the bars. Jugglers, tightrope walkers and trained-cat acts fill Mallory Square at sunset, singer-songwriters play along Duval Street every night, and drag cabaret is a long-standing local tradition. The Tennessee Williams Theatre and a winter symphony season cover the formal side, though summer programmes are thin.

Both are restful because of their slow pace rather than their spas, and neither has a bathing tradition. Clearwater's calm is that of a low-rise retirement town, with hotel pools, balconies and early nights, interrupted only by spring break and the summer heat.

In Key West the quiet is found in Old Town guesthouses built around small pools and gardens, and yoga and massage are easy to find. The party on Duval Street is never far away, though, so choose a residential street and avoid festival weekends.