Havana or Key West?

Neither city is built for lying on the sand, and the sea works differently in each. Havana has no beach in the centre. You take a taxi half an hour east to the Playas del Este, long white-sand strands like Santa María del Mar and Guanabo. On weekends they fill with Cuban families and music.

Key West's own beaches are small, with imported or coral-rubble shores, but the water is calm and clear because the reef breaks the swell. People there spend their sea time snorkelling from boats. For a proper sandy beach day you drive an hour to Bahia Honda.

Both cities offer more pleasure than variety at the table. In Havana the best meals come from paladares in old mansions and on rooftops, cooking ropa vieja, black beans and lobster, while state restaurants are often dull. Havana's real strength is in the glass: daiquiris and mojitos in the bars that made them famous, plus aged rum.

Key West eats from the sea, with pink shrimp, grouper, stone crab and conch fritters at dockside shacks. Its Cuban influence shows in morning café con leche from takeaway windows. Key lime pie is the local obsession. Menus there are more reliable than Havana's, though the range is just as narrow.

Havana is in another league. Habana Vieja alone has four great colonial squares, baroque churches, and the Capitolio and Gran Teatro at its edge. The Morro and La Cabaña fortresses guard the harbour, and Vedado has a deep stock of art deco and mid-century buildings. Add a strong national art museum and the Museo de la Revolución, and it fills a week.

Key West's Old Town of conch cottages and Victorian verandas is lovely to walk, and the Hemingway and Truman houses have plenty of character. Two days covers it all. Hemingway connects the two, since his Finca Vigía sits on Havana's outskirts.

Both stay out late, but in different ways. Havana's nights are about dancing. Locals take salsa seriously in the clubs of Vedado and Miramar, arts centres mix DJs and galleries, and the Malecón becomes an open-air gathering. Because it's spread out, you take taxis between neighbourhoods.

Key West packs everything onto Duval Street, where you carry a drink between open-sided bars and saloons after sunset on Mallory Square. It's loud and boozy, with a long-established gay scene at the upper end. You can do it all on foot, but there's little dancing.

Key West has much more for anyone who wants to be outside, nearly all of it on the water. Snorkelling and diving boats go out to the Florida Reef. The backcountry mangrove flats are good for kayaking and tarpon fishing. The Dry Tortugas offer remarkably clear water and good birdwatching.

Havana's outdoor life is mostly the Malecón, with waves breaking over the wall at sunset. For forest trails and river pools you have to go about an hour west to Las Terrazas.

Havana has a little more reachable from it, though Cuba's best places are too far for a day. Cojímar and Hemingway's house are on the edge of town. Matanzas, with its bridges and rumba tradition, is about an hour and a half away, and Varadero's beaches are about two. Viñales and Trinidad need overnight stays.

Key West is at the end of the road. Its one great outing is the ferry to Fort Jefferson in the Dry Tortugas. Otherwise there's the drive over the Seven Mile Bridge to Marathon's turtle hospital.

Key West is the easier choice with children, mainly because the water is so gentle. They can splash in Fort Zachary Taylor's shallows, ride glass-bottom boats and take the Dry Tortugas ferry, and the town has an aquarium and a butterfly conservatory. Just keep them away from Duval Street at night.

Havana greets children with real warmth, and the classic-car rides and cannon-lined fortresses go down well. But broken pavements, heavy heat and hard-to-find baby supplies and medicines make it better for older children than for toddlers.

Key West is far simpler. Old Town is flat and compact, and you can reach nearly everything by bicycle or on foot from Duval Street. You only need wheels for the rest of the Keys.

Havana's old town is walkable too, and the Malecón takes you on to Vedado. Beyond that, you'll be agreeing fares with drivers of classic cars, shared almendrones and coco-taxis, because the buses are hard for visitors to use. Uneven pavements and dim streets mean you need to take care after dark.

Neither is a place to shop for clothes or brands. What's worth buying in both is local, and in both cases it's cigars and art. Havana adds aged rum, coffee, and work from studios in Habana Vieja and Vedado, plus a big harbourside craft market. Key West has Old Town galleries of tropical painting, sponge and shell shops, and Key lime soap among the T-shirts on Duval.

Havana is much cheaper if you travel the local way. Casas particulares with breakfast, shared taxis, snacks and live music cost little. State hotels and smarter paladares charge foreign prices, and you need to bring plenty of cash.

Key West is expensive across the board. Limited land keeps rooms dear, Duval Street charges resort prices for drinks, and the boat trips that are the reason to come add up fast. Free sunsets and cycling soften the bill, but only a little.

Music is one of the main reasons to choose Havana. Son, bolero and rumba are played well even in modest bars from midday. The Vedado jazz clubs draw the island's best players. The Ballet Nacional de Cuba dances at the Gran Teatro, and there's rumba at Callejón de Hamel on weekends.

Key West's music is friendly bar entertainment: singer-songwriters and cover bands on Duval, drag cabaret, and the jugglers and cat acts at Mallory Square's sunset. Its formal stages are small and quiet in summer.

Key West is the better place to slow down. Guesthouses built around small pools and gardens on quiet Old Town lanes are easy to find, as are resort spas, massage and yoga. You just need to stay well away from the bars.

Havana's restfulness comes from its pace: rocking chairs in colonial courtyards and long shaded afternoons. Noise, heat and exhaust fumes undo much of that, and spas are scarce, so a leafy Vedado guesthouse is the best bet.