San Francisco

Sailing, hiking, biking, and snacking around the city

San Francisco! That fabled city of cold summers and thick fog, ornate victorian rowhouses, iconic orange bridges, and burritos big enough to feed a family. It’s an endearingly beautiful city, and an important one too: often at the vanguard of emerging trends in culture and counterculture, San Francisco is a bastion of inclusivity and experimentation, and a wave of tech innovations currently sweeping the world. The last time Emanuel and I visited together was on our Pacific Coast bike trip back in 2010, when we were young and spry and the thought of sitting on a bicycle saddle every day for 2 months was exciting. This time we were invited down by one of the internet companies disrupting the very experience of travel itself — Airbnb.

We’ve of course used Airbnb to find accommodations a few times in our travels: in Toronto, in Seattle, and more recently in Paris. But this was something new — this wasn’t just about cool places to stay, this was about meeting people, about exploring the city with a more intimate and insider perspective, about creating shared experiences.

Airbnb Experiences is a curated series of excursions and activities planned and hosted by locals. Airbnb had been fine tuning and guinea pigging it for months and invited us down to test out the latest incarnation. We were given 3 general options for the type of trip we wanted: foodie, local neighbourhood culture, or outdoor activities. While each of the options had appeal, we jumped at the opportunity to see some the city’s impressive natural landscapes: the staggering redwoods, the golden hills, the rocky cliffs plunging down into a crashing blue-green sea, the succulents and palms and eucalyptus galore. Plus rumour had it we might get to go sailing.


Starting our first day with a quick coffee at Four Barrel in the Mission, we made our way to the Embarcadero. According to our itinerary we were going sailing on the bay with AC SailingSF, and while I’d been on a laser (a really small sail boat of sorts), I had never been on what I thought of as a proper sail boat. We met up with the rest of the Urban Naturalist crew — friendly faces from Chicago, Texas, North Carolina, Phoenix, and Scotland to name but a few — said our introductions, and boarded a boat. Christened USA 76, the boat was a recently retired America’s Cup racing yacht… which, I admit, didn’t mean much to me at the time, but once we got going I quickly realised what it meant to be on a racing boat: it’s fast, really fast. The crew was great and made sure everyone participated hoisting the sails and having a hand at the helm. With the wind whipping our hair and the salty spray fresh in our faces we heard tales of epic race rivalries and learned the finer points of sailboat physics and construction, all the while holding on for dear life and trying not to toss our cookies. It was a grand time, and one heck of an experience to get our trip underway.

After a couple hours of barfing in the bay sailing, we emerged onto blessed dry land, grabbed a coffee from Beacon Coffee & Pantry, hiked up Lombard St, and wandered around aimlessly before heading down to Baker’s Beach to miss the sunset.


The following morning we returned to the Mission for a bike tour through the city with Pedal Inn, who got their start (and their name presumably) creating fun overnight bicycle adventures into the surrounding countryside. Our host Nick was extremely hospitable and the whole day kind of just felt like we were hanging out with old friends. We started out in Southeast Mission and cut across 26th and then north to see numerous murals and some of the city’s oldest surviving buildings including the old Misión San Francisco de Asís, dedicated in 1791. Then on to beautiful Mission Delores Park, a tasteful treat from Hot Cookie in the Castro, and finally towards Golden Gate Park via the Wiggle bike route. And boy, did that route wiggle! One of the only flat bike paths extending from Market Street to Golden Gate Park, the route turns this way and then that way then this way again to avoid the numerous hills the city is so famous for. Nick gave us a tour the entire way pointing out anything and everything of significance which gave us a great insider's view of the city from both a historical and modern standpoint.

Stopping in Golden Gate Park for a picnic lunch, we feasted on bánh mì sandwiches and lounged in the tangled shade of an old cypress tree. Satiated and restored, we toured the gardens for a spell, then rode over to a viewing tower in the De Young museum for a look out over the park and the city, before continuing on to Bakers Beach to catch a glimpse of the orange bridge and get soaked by a rogue wave or two. And then! We had to race back to the Mission, drop the bikes off, chug a local brew, pet Squirelly Joe (Pedal Inn’s resident cat), call an Uber, and finally head out to the Presidio for a sunset barbeque and some music-making well into the night. A good day.


On our third day we made an extra effort to get up early to squeeze in a breakfast at the beloved Tartine Bakery. We arrived to a long line that only seemed to snake further and further down the sidewalk as each minute passed. We tucked in to a croque monsieur topped with mushrooms and a giant slice of quiche before dashing out to catch the 10am ferry to Sausalito. A beautiful 30 minute ride across the bay, the ferry offers nice views of the city skyline, Alcatraz, and the Golden Gate Bridge. We’d heard the day before about a great white shark attacking a seal in the bay which sounded like nothing short of a blood bath, and I couldn’t help but constantly peer over the edge of the boat for any finned foes in the murky murderous waters. But sharks couldn’t hold my mind for long. Today we were hiking through Muir Woods.

Once covered in over 2 million acres of giant coastal redwoods from Oregon down to Monterey, California’s old growth forests were quickly decimated when the logging companies moved in. Spared due to its relative inaccessibility, Redwood Canyon caught the attention of William & Elizabeth Kent, who quickly purchased the land and donated it to the Federal Government to save it from destruction and preserve it for generations. With Teddy Roosevelt’s blessing, they renamed it Muir Woods National Monument in honour of their friend John Muir, the famed turn-of-the-century outdoorsman and iconic conservationist whose efforts helped give birth to the National Park system and continue to inspire people to this day.

Disembarking the ferry, we walked over to Philz Coffee for a mojito ice coffee and to meet up with Niki from Marin Outdoor Adventures. We all packed into her van and rode up a winding road into the hills towards Mt Tamalpais. About halfway up we pulled over at the Ocean View trailhead to began the slow hike back down again, when Niki pulled out a book and read to us a passage about mindfulness and being in the moment. This wasn’t just about showing us some old giant trees; she really wanted the journey to mean something, to quiet us, make us present, to leave a lasting and meaningful impression. We plodded down the sun-baked hill into the forested valley, leaving the sun and heat behind us as the trees grew larger and larger, a giant green arching canopy far above. We sat for a quiet moment by a mumbly murmuring creek, then continued on into the main Muir Woods area, busy with people now, and dwarfed by ever more giant trees. Exiting at the main parking lot, we once again packed into the van and drove back up into the hills, this time to Muir Beach Overlook. We finished the day by cracking open some beers, enjoying the good views, and feasting on a tasty little picnic lunch. Then back to the ferry and back to the blinking city on the bay.


The next morning we set our alarms for black-skied 5am, hopped in an Uber, and ventured towards the Headlands to catch sunrise with the crew. There’s something to be said about the quietness of the city in the dark stillness of predawn, the hush of the empty roads before the city comes alive. We crossed the Golden Gate Bridge, got our driver lost, found our way again, then hiked in the twilight to the top of Slacker Hill. Hoping to see a giant bank of fog rolling in, we were met with magnificent clear skies instead, and stood mute as a hazy sun slowly lit up the landscape. I have a hard time waking up early in the best of times, but seeing the first rays of light coming over the horizon makes all the crusty-eyed discomfort worth it. We walked along the top of the ridge out towards Battery Spencer for a bit before scrambling down the hill onto the road for a couple more photos and to hail a car.

Returning to the city, we stopped in at The Mill for some much vaunted ‘hipster toast.’ Made with a selection of house-baked bread, they offer a variety of flavours and toppings, including the hot buttered traditional cinnamon sugar, a combo that can never be beat. When I was little I used to wake up extra early before my mom and sneakily make cinnamon toast, then later when she was up I’d act all chill and make myself a second more respectable breakfast of peanut butter on toast.

We were supposed to go do a wine-soaked brunch later that morning, but tired and in need of some chill time, we wandered back over to Golden Gate Park, found a little hill, and lay down for a snooze in the grass. Waking up with November sun burns, we reserved the remainder of the day for coffee and burritos and a little sunset excursion down to Sutro Baths.


Trying to make the most of our last morning in San Francisco, we woke up early for one last sunrise on Mt Davidson. Flanked with eucalyptus groves, the hilltop park is a magical spot to watch the summer fogs roll in. Our pals Sam and Wes joined us as the warm glow of morning light flooded the city far below, revealing neighbourhoods that had just a minute earlier been hidden in the quiet of a muted dusk. But no fog. Not today. We learned that November is usually warm and clear, indeed far more summer-like than it is in summer. For cool foggy days we would have to come back in August.

Returning to The Mill, we met up with the rest of the gang for one last cinnamon toast and a couple of hot beverages. It was the end of the trip and everyone was dispersing back to their own corner of the continent and the globe. They were a great group and we had had a lot of fun. After saying our farewells we went back to our Airbnb to pack up, had a coffee at Ritual, then went to <El Farolito for one last kick at the burrito can. It was kind of the best way to end the trip for me – with my favourite adventure bud by my side and a burrito the size of my face.

Big thanks to Airbnb for hosting us!