In Old Havana, shadows seem to dance along the area’s 16th-century limestone castles, wedding cake palaces and colonial mansions—it’s a photographer’s dream. A day spent strolling the city’s sunny cobblestone streets, listening to the seductive sounds of Cuban rumba and watching the waves crash on the Malecón will feed your senses and your soul.

7:30 to 9 a.m.

If you’re based in Varadero, grab breakfast at your resort and arrange with your concierge for a new taxi (with air-conditioning) to pick you up and drive you into Havana. Stop for a photo op at the Puente de Bacunayagua, Cuba’s highest bridge. When you arrive in the city, hop out at the Iberostar Parque Central Hotel and arrange for a pickup time with your driver.

9 a.m. to noon

Take a walking tour with San Cristobal Agencia de Viajes—your guide will meet you in the Iberostar lobby. Get the fascinating background on the city’s turbulent history as you stroll through the main squares of Old Havana: Plaza de San Francisco de Asis, Plaza Vieja, Plaza de Armas and Plaza de la Catedral. Don’t miss the giant iconic image of Che Guevera in Revolution Square.

Noon to 3 p.m.

Return to the Plaza Vieja to sample delicate pastries and sandwiches at the Café el Escorial. For great souvenir shopping, follow Calle San Ignacio to the San Jose Handicraft Market on the harbour. There’s a huge selection of colourful paintings on canvas and dozens of jewelry and craft stalls.

3 to 4 p.m.

Catch a jingly three-wheel trike to El Floridita bar, one of Ernest Hemingway’s favourite hangouts and the legendary home of the daiquiri. A sultry vocalist and her band purr a hot rumba while you strike a pose with the life-sized bronze statue of “Papa” at the end of the bar.  

4 to 6 p.m.

Out front of the Iberostar Parque Central Hotel you can hire a 1950s chrome dream mobile ($35 per hour). With the wind in your hair, cruise alongside the Malecón—the shoreline walkway that’s a favourite of locals and tourists, alike. Stop in at the Hotel Nacional de Cuba, the pre-revolutionary hangout of molls and mobsters. 

6 to 9 p.m. 

Watch the sun sink into the sea from the balcony of the mid-century modern Paladar (privately owned restaurant) Vistamar. Try the ropa vieja, (“old clothes”), a Cuban dish of slow-simmered beef and peppers. Back at the Iberostar, enjoy the rooftop poolside patio where the house band will serenade you before your ride home. 

Getting There: WestJet flies to Varadero eight times a week from Toronto, Calgary and Montreal.