Havana

For two centuries, much of the gold and silver Spain pulled out of the Americas passed through one harbor: Havana's. Once a year, treasure ships from across the New World gathered in Havana Bay, then crossed the Atlantic together as a single guarded fleet.

All that wealth made Havana a magnet for pirates. The city was raided and burned more than once, so Spain ringed the harbor with massive stone fortresses, some of the oldest in the Americas.

Founded in 1519, Havana grew into one of the largest cities in the New World. By the 1750s it was bigger than Boston or New York.

It was so valuable that in 1762 the British sailed in, broke through the defenses, and seized the city. They held it for about a year, then handed it back to Spain in a swap, trading Havana for Florida.

Spain ruled Cuba until 1898, when the American battleship USS Maine blew up in Havana harbor, killing 266 sailors. The cause was never proven, but it helped push the United States into war with Spain, and Cuba won its independence soon after.

The biggest break came on January 1, 1959, when the revolution led by Fidel Castro toppled the dictator Batista. A US trade embargo soon followed and froze the city in place. That's why the streets are still full of polished 1950s American cars, kept running for decades because no new ones could come in.

Wander Old Havana, a UNESCO-listed maze of colonial squares, pastel buildings, and live music spilling from doorways. Walk the Malecón, the seawall where the whole city gathers at sunset.

Tour El Morro, the clifftop fortress guarding the harbor, and see the Capitolio, which looks strikingly like the US Capitol. Ride through the city in a vintage convertible, then visit Finca Vigía, the hilltop home where Ernest Hemingway wrote for 20 years.

Eat ropa vieja, shredded beef stewed in tomato, and moros y cristianos, black beans and rice cooked together. Cool off with a batido, a fresh-fruit Cuban milkshake.