San Francisco's Scenic Urban Hike Has Hidden Stairs, Hilltop Views, And Coffee Stops

From Alcatraz, the infamous island-bound penitentiary filled with history and mystery, to the world's worst tourist trap, Fisherman's Wharf, San Francisco is brimming with iconic attractions. Then there are the city's off-the-beaten-path allures that are waiting to be discovered, the calm, hidden gems in the center of the city that offer a quiet retreat away from the crowds. There's nowhere like the City by the Bay.

If you're planning a visit to San Francisco and are looking for a serene and scenic escape from the buzzing tourist spots, then adding an urban hike to your itinerary is just the ticket. Comprising picturesque parks, famous streets, hidden stair paths, and plenty of delicious pit stops, this 4-mile loop walking trail (shared by @the.brokencompass on Instagram) is perfect for exploring some of San Francisco's most-photographed landmarks. So, put on your walking shoes, prepare for those infamous hills, and get ready for an urban adventure on this picture-perfect walking tour through San Francisco.  

Taking just under two hours to walk without stops — and there will be plenty of stops — your urban hike starts off sweet with Whack Donuts! at 4 Embarcadero Center. The Black-owned bakery serves a variety of classic and unique flavors, with vegan and gluten-free options as well. Plan for a morning departure, and treat yourself to a delectable donut breakfast before strolling on to Transamerica Redwood Park. A serene spot in the center of downtown, the gorgeous park is home to over 50 giant redwoods looming over picturesque paths, quiet benches, and a trickling fountain dedicated to Mark Twain. It's also the perfect spot to relax before the ambitious climb up the Vallejo Stairway, which ascends to a sweeping view of the city from Ina Coolbrith Park.

After catching your breath at the top, make your way down for a caffeinated reward at Saint Frank Coffee. Then, continue on to San Francisco's scenic spot with luxe homes, cinematic beauty, and the "crookedest street in the world," Lombard Street. The steep and twisty street is one of the most-photographed in the world, with vibrant flowers and lush shrubbery lining each hairpin curve of the brick-lined road. If you're a Hitchcock fan, be sure to stop at 900 Lombard to see the home of Jimmy Stewart's character's house in "Vertigo." If you continue to the top of the hill, you may experience a little vertigo yourself, but you'll also get a dazzling view of the city and the crooked street below.

The second leg of the journey begins in Fay Park, a charm-filled oasis adjacent to Lombard Street with whimsical gazebos, vintage lamp posts, and an enchanting rose garden. Enjoy a leisurely stroll through the park before indulging in another sweet treat at nearby Butter & Crumble. Housed in an adorable white and pastel pink facade, the women-owned bakery is packed with homemade goodies, from French-style laminated pastries to decadent crumble cakes.

After resting your legs and filling up on sugary treats, you'll be geared up to climb Coit Tower. Rising from Telegraph Hill like a majestic Romanesque column, the historic white tower has 13 flights of steps, granting unparalleled city views at the top. If your legs are aching for a break, don't worry, it's all downhill from there as you take the wooden Filbert Steps back to street level. Finally, reward your 4-mile trek with one last food stop at Burger Littles, whose mouthwatering smash burgers are anything but little.