Driving in Havana and its environs isn't as daunting as you might think; there are relatively few cars on the roads, and most drivers aren't overly aggressive. Remain alert and flexible and watch out for bicycles, ciclo-taxis, and coco-taxis—not to mention pedestrians looking for botellas (rides). Road surfaces are uneven, so if you drive, keep your eyes glued to the pavement. Cubans beep their horns often, though rarely in a belligerent way; this is a courteous way to let other drivers know you're coming through.
Parking isn't generally a problem in Havana as there are still relatively few automobiles circulating. Even around Plaza de las Armas or Plaza de San Francisco de Asís it's usually possible to find a parking spot. You will, however, encounter freelance parking attendants who will keep an eye on your car for a dollar up front, a bargain automobile security system.
To travel from Havana to Cojímar, Playas del Este, Matanzas, and eastern Cuba, take the tunnel under the harbor to the Vía Monumental and proceed due east to the Vía Blanca. To reach Pinar del Río (west), pick up Avenida de la Independencia (Rancho Boyeros) at the Plaza de la Revolución and follow it south to the Autopista Central. Turns are marked, but only once. Outside of Havana expect few road markings. Get the best map you can, and be prepared to ask for directions.
Car rentals in Cuba are expensive (450 to 550 cuc a week), and the car you reserve may or may not be available when you arrive to pick it up. Be prepared to leave a deposit of 400 cuc or more. Cubacar, for instance, has offices in the Hotel Meliá Cohiba and other major hotels; Havanautos has offices at the airport and major hotels; Panautos, which has offices all over Havana; and Transgaviota, which rents cars with or without a driver. All companies, however, are government operated.
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