Weekend Excursion: 72 Hours in San Francisco

Explore the City by the Bay

By: Josiah Roe

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About a week ago it was 85 degrees in San Francisco. In April. And in two months it will be 50 in the middle of the afternoon. No-one knows who said “the coldest winter I ever spent was a summer in San Francisco” but it is as true today as it was then.

From June to September the blustery winds blowing Karl the Fog through the Golden Gate chills shorts-and-T-shirt-wearing tourists to the bone, leaving many wondering “just when do I get to see the beautiful city in all those movies?” As any local will tell you, San Francisco has two summers: a brief one in April-May just after the rains and before Karl the Fog arrives in force, and then another for six weeks beginning in late September and through October.

My personal favorite is our summer in May. The rains leave Northern California looking so emerald green it could easily be mistaken as western Ireland. The lingering clouds provide breathtaking sunsets and sunrises over the ocean. The rivers are full. Everything is alive.

It’s paradise.


Secret Hike and Picnic with a View at Tank Hill | Photo: Josiah Roe

Pick a place to stay that is centrally located: think NOPA, Upper Haight, Lower Haight, and even the Inner Sunset or Inner Richmond. First things first is a sunrise run up Twin Peaks over to Mount Sutro and down through The Enchanted Forest aka the “Sutro Open Preserve” to Stanyan Street. On the ascent up Ashbury/17th, be sure to head up the trail on the northern face of Tank Hill. Add Buena Vista Park to the beginning and you can get almost 1K feet of elevation gain. The views are spectacular and the downhill from Mount Sutro through a Eucalyptus cloud forest ravine is, like the name implies, enchanting.

Catch a Sunset at Grand View Park (“Turtle Hill”) | Photo: Josiah Roe

After a shower, head over to Zazie in Cole Valley for breakfast. Expect a wait and grab a coffee next door at Pete’s. To kill time, head a block down Cole street to Tantrum and pick up a present for your kids/nephews/nieces. Be sure to get a pitcher of the pomegranate mimosas!

After breakfast, walk down Cole Street and hang a left on Haight to checkout Amoeba Records. Then head east back on Haight Street for some window shopping; be sure to check out Loved to Death and the Bound Together Anarchist Collective Bookstore. Make sure to grab a silly costume from Costumes on Haight; you’ll need it later.

At any of the markets on Haight, pick up some munchables and a couple bottles of wine and hang a right on Pierce street. Pop your first bottle at Duboce Park, then press on from there on Noe towards Dolores Park. Snag a spot on the grass at the top of the hill, near Church and 20th. It’s a park day: have a robot dance party, enjoy some goodies from the Truffle Man, and by all means, get weird and have fun in that costume you bought earlier.

About 45 minutes before sunset, summon a Lyft/Uber to take you to 16th and Noriega to head up the Moraga Street Steps and to take in a sunset at Grand View Park. Bring a bottle of champagne and someone you’re into.

From Grand View, walk down the 15th Avenue Steps and go right on Irving. Put your name on the wait list at San Tung and then walk up to 9th avenue to the Oriental Art Gallery and buy some pins. Check the time on San Tung again. If you still have a wait, duck into the New Eritrea Restaurant & Bar and grab a glass of their house made honey and and white wine combo.

After dinner, head over to the 120 year-old Little Shamrock for a nightcap.


Hike Matt Davis-Steep Ravine Loop | Photo: Ryan Vermillion

Grab some quick coffee and trail fuel at The Mill on Divisadero, and then gear up for a trail run on the Dipsea, home of the worlds oldest trail race. Take the 101 over the Golden Gate Bridge, get off at the Highway 1 exit for Muir Woods/Stinson Beach, and take a right on Panoramic Highway towards Muir Woods. Park on Panoramic Highway just after the turnoff towards Muir woods.

There are several loops from this starting point, depending on your ability, and all go through the gorgeous Muir Woods: you can take Dipsea up to Ben Johnson and then back down, Dipsea to Steep Ravine to Ben Johnson, or a totally epic loop of Dipsea to Matt Davis and down Ben Johnson (~13 miles). Map here.

After your run, drive Highway 1 over to The Pelican Inn in Muir Beach for a victory beer and lunch on the grass. Stop off at the Muir Beach Overlook for some epic coastal views and depending on the time of year, see nesting red-tailed hawks and migrating grey whales.

On your way back to town checkout the San Francisco Running Company for any running gear you may need, and walk across the street to Proof Lab, an amazing outdoor, skate, and surf apparel shop.

Capture Sweeping City Views from Bernal Heights | Photo: Mitchell Phun

For dinner, head over to Emmy’s Spaghetti Shack on Mission Street for some killer meatballs. Head up Mission Street to the 3300 Club for a shot of Fernet to settle the stomach, then head up Virginia Street and hike to the top of Bernal Hill for 360 degree views of San Francisco at night. There may even be a piano.


Beach Bonfire at Ocean Beach | Photo: Josiah Roe

Start your Sunday off at the locally owned Haight Street Market with Blue Bottle Coffee and a smoked-salmon everything bagel. Kick it on the parklet outside, watching the “Walks of Glory” as partiers from the night before head home.

After breakfast, fill your backpack(s) up with snacks and wine from the market and head down Haight Street into the world’s greatest urban park: Golden Gate Park. One could spend a lifetime exploring its 1,000+ acres and still not find all there is to discover.

Your eventual goal is Ocean Beach and the Pacific Ocean, so wander in a generally western direction taking whatever detours feel right. Be sure to pass Hippie Hill and the never-ending-drum-circle, watch a few rounds on perfect greens of the San Francisco Lawn Bowling Club (no bocce allowed!), visit the National AIDS Memorial Grove and the Dry Creek ravine on the west end.

Throw down a blanket wherever you feel like relaxing. You could also go for a Boat Ride on Stowe Lake, or duck into the Conservatory of Flowers, or the De Young Museum, the Academy of Sciences, or the Botanical Gardens.

A must-see, particularly in the spring, is the Japanese Tea Garden. Visit the tea house and enjoy tea and mochi overlooking the gardens and waterfalls.

There are great views to be found at the summit of Strawberry Hill, located on an island in the middle of Stowe Lake.

As you head west and pass under Crossover Drive, the park gets significantly more wild. It is possible to get turned around on the many trails, but keep your phone and Google Maps on you and keeping heading towards Speckles Lake and take a tour of the San Francisco Model Yacht Club, then practice your casting at the Golden Gate Angling and Casting Club.

From there, keeping heading west, stopping to check out the bison and the windmills, making your way to Ocean Beach.

Overlooking Ocean Beach is the fantastic Beach Chalet restaurant and brewery. Leave the upstairs for tourists and head out back and have a beer and a late lunch on the lawn.

A couple hours before sunset, walk a block away to the Safeway on La Playa Street and stock up food and firewood. Text all your friends old and new, and head over to Ocean Beach for a bonfire. Be sure to check that it’s not a spare the air day. Have no worries if all the fire pits are taken: this is San Francisco, cozy up with another group and let the good times roll. It can get cold at night on the beach, so be sure to bring warm clothing and blankets.

Finally, catch a Lyft back to the iconic Aub Zam Zam in the Haight for a shot of fernet to warm the soul. As the poem on their cocktail napkin goes:

“Come, fill the Cup, and in the fire of Spring
Your Winter-garment of Repentance fling:

The Bird of Time has but a little way

To flutter—and the Bird is on the Wing.”
- From ‘The Rubaiyat of Omar Khayam’

Cover photo: Josiah Roe

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Please respect the places you find on The Outbound.

Always practice Leave No Trace ethics on your adventures. Be aware of local regulations and don't damage these amazing places for the sake of a photograph. Learn More

Please respect the places you find on The Outbound.

Always practice Leave No Trace ethics on your adventures. Be aware of local regulations and don't damage these amazing places for the sake of a photograph.