San Francisco

Start at the Ferry Building, that beautiful Beaux-Arts landmark where locals queue for Blue Bottle coffee before work. The building itself is worth a pause—its 245-foot clock tower has watched over the bay since 1898.

Head south along the wide, palm-lined promenade. The Bay Bridge towers to your left, its lights still twinkling if you're early enough. Pass the quirky Cupid's Span sculpture—a giant bow and arrow that looks like it fell from Olympus—and continue toward Oracle Park, where the Giants play on summer nights.

The route flattens beautifully along Mission Creek, where houseboats bob gently and cormorants dry their wings on wooden posts. This is working-class San Francisco, hidden in plain sight. Turn back at the end and let the city skyline pull you home.

The crown jewel of San Francisco running. This is the run that made you download Portjogger in the first place.

From the working fishing boats of Hyde Street Pier—where Dungeness crab is unloaded before dawn—trace the waterfront through the tourist chaos of Pier 39. The sea lions are louder than you'd expect, their barking carrying across the marina.

Past the historic ships at Aquatic Park (the vintage submarines are worth a detour), you enter the magic of Crissy Field. Here, the path becomes a meditation. Marsh grass sways on one side, kitesurfers launch on windy days, and the Golden Gate grows larger with every stride.

End at Fort Point, directly beneath the bridge. The scale is almost overwhelming—the towers stretching 746 feet above you, cars humming across the deck, fog streaming through the cables. Touch the red-orange steel. You've earned it.

For those who want their waterfront running wild.

This rugged trail along the northwest edge of the city offers Pacific views that have nothing to do with the familiar bay. This is the open ocean—cold, dramatic, endless. Cypress trees cling to the cliffsides, twisted by decades of wind into sculptural shapes.

The trail demands attention. Roots cross the path. Stairs climb and descend with no warning. Eagle's Point offers a view that stops runners mid-stride: the orange span of the Golden Gate against the blue Pacific, the Marin Headlands rolling green beyond.

At the western end, the Sutro Baths ruins appear like a ghost—massive concrete pools that once held 10,000 swimmers now filled with seawater and memories. The adjacent Cliff House has served drinks to runners (and everyone else) since 1863.