Telegraph Hill is the best climb in San Francisco, and the secret is that the hard side is the beautiful one. The east face is too steep for cars, so Filbert Street simply turns into a wooden staircase and climbs the cliff through private gardens to Coit Tower at the top. Start at the base on Sansome, look up, and begin.
The Filbert Steps run up through the Grace Marchant Garden, thirty years of one woman's planting on a slope that used to be a dump — stay on the steps and walk the green tunnel. Branch onto Napier Lane, a plank boardwalk of pre-earthquake cottages, and listen: a feral flock of cherry-headed parrots lives in these trees and screeches over the hill most afternoons. The steps top out at Pioneer Park, the green collar around the tower.
Then go inside Coit Tower, not just up it. The ground floor holds 1934 New Deal frescoes — California labour, city streets, a little radicalism that caused a fuss when they were unveiled. They're free. Pay for the lift if you want the 360 at the top; the 39 Coit bus takes you back down.