Key West or Trinidad, Cuba?

Both have warm, calm water sheltered by a reef, so the difference lies in the shore. Key West's town beaches are small: Smathers has imported sand, Fort Zachary Taylor has coral rubble, and seaweed washes in after storms. A proper beach day means driving about an hour to Bahia Honda.

Trinidad has the better sand close to town. Playa Ancon is a long, pale strip about 15 minutes away, with snorkelling off the reef, and La Boca adds a smaller local shore. The choice stops at those two, but neither needs a boat or a long drive.

Both kitchens draw on the sea and on Cuban cooking, and Key West offers more variety. Pink shrimp, stone crab, conch fritters, Cuban sandwiches from takeaway windows and a few more ambitious Old Town dining rooms make for a few days of good eating, even if Duval Street is mostly bar food.

In Trinidad the best meals are often at your casa particular: rice and black beans, roast pork, ropa vieja and lobster, with a canchanchara alongside. Supplies are unpredictable, so menus repeat, and there is no street food or market hall to fill the gaps.

Trinidad's old centre carries more weight. Cobbled streets, pastel houses and the Plaza Mayor, with its church and planters' mansions, make up a sugar-era town preserved almost whole. UNESCO lists it together with the valley beyond, and the tower of the Palacio Cantero looks over the rooftops to the mountains.

Key West's Old Town of conch cottages and deep verandas is handsome in its own right and is best seen on side-street walks. Its museums tell an engaging story of wreckers, Hemingway and Truman, but they are small, and the whole set takes about two days.

Key West has more places to go and stays out later. Once the sunset crowd leaves Mallory Square, Duval Street becomes a long run of open-sided bars and rooftop decks where you carry a drink from one to the next into the small hours, with a long-established gay scene at the upper end. The tone is loud and boozy rather than stylish.

Trinidad's nights are friendly but small: rum cocktails and salsa on the steps beside the Plaza Mayor, a few courtyard bars and a club inside a cave on the hill. Every evening follows the same pattern, so a few nights are enough.

Both are strong outdoors, but on different ground. Key West's outdoors is almost all water: boat trips to the Florida Reef, kayaking and fishing in the mangrove backcountry, and the remote Dry Tortugas. The island is flat and has nowhere to hike.

Trinidad has the land as well as the sea. The Escambray mountains rise behind the town. In Topes de Collantes, forest trails lead to the falls at Salto del Caburni and El Nicho, and horse rides cross the Valle de los Ingenios. With reef snorkelling off Ancon as well, it has the edge for anyone who wants to walk.

Here Trinidad pulls well ahead. The Valle de los Ingenios, with its ruined sugar mills and the Manaca Iznaga tower, begins at the edge of town. Cienfuegos, Sancti Spiritus and Santa Clara each make a full day out, though you need a shared taxi, hired car or tour to reach them.

Key West sits at the end of the road. The ferry to Fort Jefferson in the Dry Tortugas is a memorable outing, and the drive over the Seven Mile Bridge to Marathon has its moments, but Miami and the Everglades are too far for a day.

Key West gives children more to do, even though it is not designed around them. Calm shallows at Fort Zachary Taylor, glass-bottom boats, a small aquarium, the butterfly conservatory and trolley tours will fill several days, as long as you keep clear of Duval Street after dark.

Trinidad welcomes children warmly, and the shallow water at Ancon makes a good day out, but little else is aimed at them. Large, uneven cobbles defeat pushchairs, and power cuts and a shortage of familiar foods and medicines make it hard going with small children.

Key West is a flat, compact island where bikes, electric carts and scooters are everywhere, so it is far easier to move around. Old Town, the bars and the harbour are all close together. You only need a car or a shuttle to reach the rest of the Keys along the Overseas Highway.

Trinidad's old town is also easy to cover on foot, but the cobbles are rough and the streets slope. Beyond the centre there is no transport a visitor can rely on, so Ancon, the mountains and nearby towns mean taxis, hired cars or tours. Coaches to Havana are slow.

Neither is a place to come for shopping, but what you take home differs. Key West sells souvenirs along Duval Street, and the more interesting finds are Old Town's galleries, hand-rolled cigars and the sponge and shell shops by the harbour. Trinidad's offer is handicraft: hand embroidery and crochet in the open-air market lanes, pottery from family workshops and small art galleries, with rum and cigars best bought at state shops.

Trinidad costs far less. A room in a casa particular is cheap and often includes breakfast, and music in the squares is close to free. The extra spending goes on taxis, tours and paladar meals priced for visitors. Bring cash, as cards are often not accepted.

Key West costs far more than most American towns, with resort prices on rooms, drinks and boat trips that are highest in winter. Walking and cycling, the free sunset on Mallory Square and the Cuban takeaway windows help, and late summer is the cheapest season.

Trinidad's music has more depth. Bands play son, salsa and bolero every night at the Casa de la Musica and the Casa de la Trova, the Palenque de los Congos Reales stages Afro-Cuban drumming and rumba, and locals dance alongside visitors. The town has no formal stage at all, though.

Key West has what Trinidad lacks in that respect: the Tennessee Williams Theatre and a symphony orchestra in winter, along with drag cabaret and the sunset performers on Mallory Square. Most of the bar music is cover bands and singer-songwriters, fun rather than memorable.

Key West is the easier place to unwind. Its quiet Old Town lanes have guesthouses set around small pools and gardens, and resort spas, massage and yoga are easy to find. It makes for a calm stay, as long as you sleep away from Duval Street.

Trinidad has a slow rhythm, shaded courtyards and rocking chairs on the doorsteps, but little more than a few hotel massages near the beach. Roosters at dawn, horse carts on the cobbles, late music and power cuts that stop the fans all make rest harder.