Always eerie Alcatraz, a former federal prison perched on an island in San Francisco Bay, is even more chilling on guided evening tours. Circle the island by ferry, and see the various points from which attempted escapes were made. Then, once on solid ground, follow your guide to hear about some of the prison’s most notorious inmates—people like Al "Scarface" Capone, George "Machine Gun" Kelly, and Robert “Birdman" Stroud. Step inside an actual cell, preserved in all its forbidding austerity, and imagine the loneliness of staring at the nearby city, sparkling in the night. Bringing it all into sharp focus is an award-winning audio presentation “Doing Time: The Alcatraz Cellhouse Tour,” during which you’ll hear firsthand descriptions of what daily life was like on the inside, what it was like to withstand the trials of solitary confinement, and descriptions of breakouts from ex-correctional officers who worked and lived on the island.
But the tour isn’t all gloom-and-doom incarceration stories, as fascinating as they are. It’s also a great chance to get amazing sunset shots of the Golden Gate Bridge, and the city skyline lighting up as the sun goes down. Bundle up—the island can be especially chilly, especially when fog rolls in. Space is limited; advance reservations are required. Know ahead of time that roads and walkways on the island are steep, but there are plenty of places to stop and take a break along the way. Appropriate footwear is recommended. If mobility concerns are an issue, find out how to take advantage of the park’s Sustainable Easy Access Transport (S.E.A.T.) tram.