Alcatraz

In 1854, the West Coast’s first lighthouse was built on San Francisco Bay’s Alcatraz Island to guide the ships coming and going through the Golden Gate. Government officials quickly decided that the tiny, 22-acre island aptly nicknamed “The Rock” was also an ideal location for a federal penitentiary—so close and yet so far from bustling San Francisco. The island’s sheer cliffs were surrounded by perilous currents, extreme tides, and hypothermic water temperatures, so escape from this prison seemed impossible.

Alcatraz served as a military prison from the time of the Civil War until 1934, when it was converted to a civilian penitentiary. Although it operated for only three decades, The Rock remains fixed in the American psyche as the ultimate penal colony—thanks in part to Hollywood films such as the Clint Eastwood classic Escape from Alcatraz. The prison housed some of the country’s most notorious bad guys: Al Capone, George “Machine Gun” Kelly, and “Bird Man” Robert Stroud, a murderer who became an expert in ornithological diseases.

Take a ferry to the island and explore the abandoned prison by day or by night. The 20-minute boat ride is reward enough with its invigorating salt spray and expansive bay views, but your ferry ticket also covers admission to the island, an optional ranger-led tour, and a 40-minute self-guided tour of the cell house with an audio headset. The narrated program, “Doing Time,” weaves together voices of actual inmates and prison guards with actors’ reenactments, making the prison’s empty walls come to life with tales of food riots, solitary confinement, and escape attempts. A total of 23 prisoners tried to break out of Alcatraz, but all were killed or recaptured except for three men who escaped in 1962. Their whereabouts are still unknown.

As you tour, step inside the open cells and imagine the tedium and loneliness. Walk around the guardhouse, exercise yard, and the surprisingly lush gardens that surround the buildings. If you’re visiting between late September and February 1, hike the island’s seasonal 0.7-mile Agave Trail. The spiky succulent was planted by prison guards and their families, creating a horticultural fence that deterred would-be escape accomplices from landing boats on the island. The stone-lined path meanders through a eucalyptus grove, then descends to within a few feet of the water’s edge, giving you a front-row view of boats sailing past. Hikers are also rewarded with dazzling views of San Francisco, the Golden Gate Bridge, lush Marin County to the north, and nearby Angel Island, a California state park.

Insider tips: Get to The Rock via the Alcatraz Cruises ferry from Pier 33 on San Francisco’s Embarcadero near Bay Street. Ferries usually fill up on weekends and holidays, so book your tickets at least three weeks in advance. Plan on two or three hours for the entire trip. Wear comfortable shoes for the steep walk from the dock to the prison, and bring a jacket or windbreaker for San Francisco’s famously cool weather.