Caracas

The Spanish tried to settle the Caracas valley three times. An indigenous chief named Guaicaipuro kept kicking them out.

Guaicaipuro united the local tribes and fought off Spanish colonizers for nearly a decade during the 1560s. Two settlements destroyed. Soldiers chased away. The guy did not want visitors.

It took Captain Diego de Losada and a full military campaign to finally found the city on July 25, 1567. The Spanish cornered Guaicaipuro and killed him the following year.

Caracas became Venezuela's capital in 1577 and grew rich exporting cacao, the raw ingredient in chocolate. So yes, this city helped fuel the world's chocolate supply.

Then came Simón Bolívar. Born here in 1783, he lost both parents by age nine. He grew up to become South America's greatest independence hero, freeing six countries from Spanish rule. Bolivia is literally named after him.

On March 26, 1812, a massive earthquake flattened much of Caracas. Bolívar stood in the rubble and reportedly shouted, "If nature opposes us, we'll fight against her and make her obey us." The quake helped the Spanish recapture the city, and it took another decade of war before independence stuck in 1821.

The city sits in a valley at 3,000 feet, surrounded by mountains on every side. El Ávila, the massive peak to the north, separates Caracas from the Caribbean Sea. The altitude keeps temperatures around a perfect 74°F all year.

Ride the cable car up El Ávila for one of the best views in South America. On one side, the entire city sprawls below you. On the other, the Caribbean coastline stretches to the horizon. At the top, you'll find an ice skating rink, food stalls selling strawberries and cream, and trails leading to the mountain village of Galipán.

Visit Bolívar's birthplace, a colonial house from the 1640s and one of the last ones standing in central Caracas. Grab arepas stuffed with Reina Pepiada (chicken, avocado, and mayo), order tequeños (warm cheese wrapped in crispy fried dough), or try pabellón criollo, the national dish of shredded beef, black beans, rice, and sweet fried plantains.