The highway was conceived during the military government of Colonel Marcos Perez Jimenez, after six years of engineering studies by the Ministry of Public Works. Construction began in January 1950 and was driven by a deadline: the Tenth Inter-American Conference of Foreign Ministers, scheduled for Caracas in early 1954. Two thousand workers and over 200 pieces of heavy machinery - bulldozers, tractors, trucks - labored to meet it. Among the Venezuelan workforce were 300 immigrant laborers from Italy, Germany, Austria, and the Slavic countries. The cost was staggering: $3.5 million per kilometer at the time. The highway became an emblem of Venezuela's policy of sembrar el petroleo - sowing the oil - the idea that petroleum revenue should be transformed into permanent national infrastructure. Like the Guri Dam that followed, the Caracas-La Guaira highway was meant to outlast the oil that paid for it.

The two tunnels were the engineering heart of the project. Each is actually a pair of twin tubes separated by a natural rock wall about 12 meters wide, with two lanes of traffic flowing in one direction on each side. The first Boqueron tunnel stretches 1,910 meters; the second runs 497 meters. They were built by the Morrison Knudsen Company of Boise, Idaho, at a cost of approximately $20 million, and designed by Ralph Smillie, who headed a consulting engineering firm in New York. The ventilation system was advanced for its era: sensors that automatically regulated fresh air intake based on carbon monoxide concentrations from vehicle exhaust. Vertical galleries drilled 37 meters up through the mountain served as air shafts, injecting clean air and expelling combustion gases. A central control house near the Caracas-side tunnel entrance managed ventilation, lighting, traffic signals, and emergency warnings for both tunnels.

Of the highway's three viaducts, Viaduct No. 1 became an engineering nightmare. Landslides plagued it from the 1980s onward. The 1967 Caracas earthquake had already caused severe deformation, shifting the bases of its supports toward the center of the span, cracking the columns, and buckling the roadbed upward. Successive Venezuelan governments patched and reinforced the structure but never developed a permanent solution. On January 5, 2006, the government closed the highway entirely as a safety precaution. The sudden isolation of Caracas from its coast, its international airport, and its primary port triggered political accusations from all directions: the opposition blamed Hugo Chavez's government for neglect, while Chavez supporters blamed preceding administrations for decades of deferred maintenance. A steep, narrow detour opened on February 28. The viaduct span collapsed on March 19. Construction on a replacement began immediately, and the new Viaduct 1, 900 meters long, opened on June 21, 2007.

The highway's importance to Venezuela is difficult to overstate. It connects the capital not only to the coast but to Simon Bolivar International Airport at Maiquetia, which handles some 200 daily domestic and international flights, and to the port of La Guaira, through which roughly half of all Venezuelan imports flow. Caracas sits at 936 meters of altitude, just 17 kilometers south of the sea but separated from it by a wall of coastal mountains. Without this highway, the capital is landlocked in practical terms. The road it replaced - the Carretera Vieja, with its minimum curve radius of 15 meters and 12-percent grades - was itself a replacement for the 19th-century La Guaira and Caracas Railway. Each generation has had to solve the same problem: how to get through these mountains. The highway's 36 turns, 300-meter minimum curve radius, and maximum 6-percent grade represent one generation's answer. Whether a modern railway will someday provide the next remains an open question.