steal my vacation

For My First Trip to San Francisco, I Polled 50 Friends on What to Do

Mushroom ice cream, famous tiki bars, and Mendocino excursions.

Photo-Illustration: The Strategist; Photos: Tyler Bainbridge
Photo-Illustration: The Strategist; Photos: Tyler Bainbridge

Everyone knows that person who spends weeks sniffing around travel blogs, going deep into Tripadvisor rabbit holes, collecting Google docs from friends of friends, and creating A Beautiful Mind–style spreadsheets to come up with the best vacations and itineraries possible. In this recurring series, we find those people who’ve done all the work for you and have them walk us through a particularly wonderful, especially well-thought-out vacation they took that you can actually steal.

Tyler Bainbridge is one of the editors behind Perfectly Imperfect, a newsletter “about what people are into,” which puts him at the nexus of recommendations from writers, actors, filmmakers, musicians, models, and designers, all of whom have excellent taste. So when Bainbridge began making plans for his first trip to Northern California — a Mendocino County wedding, plus a few days in San Francisco — he asked the broader Perfectly Imperfect network where he should go and what he should eat and saved everything to his Google Maps. “I compiled a list of 95 places,” he says, “so that if I happened to be in a certain neighborhood, I could easily find something that I knew came with some kind of praise.” His strategy yielded a mix of you-gotta-do-it tourist attractions and true Bay Area institutions that live up to the hype. Here, Bainbridge shares his favorite vistas, dive bars, and places to buy tourist T-shirts.

Day 1

1 p.m.: Head straight to In-N-Out

My girlfriend visited her aunt in San Francisco when she was younger and has a lot of memories of Fisherman’s Wharf, specifically walking along the pier and visiting the arcade and the Ghirardelli factory. After landing, we went there first for a dose of nostalgia. But me? I was most excited to try In-N-Out (333 Jefferson St.), as I’m a pretty big burger head and this was my first time on the West Coast. The verdict? A little overrated, but it was great for the price and how fast it was.

2 p.m.: Order a “famous” Bloody Mary and gawk at the seals …

I heard that Scoma’s Restaurant (1965 Al Scoma Way) had a famous Bloody Mary — I don’t know why it’s famous; it just says “Scoma’s Famous Bloody Mary” on the menu — and after a long flight, I wanted to have a drink on the water. And it really was a pretty good Bloody Mary. Then we walked a few minutes to Pier 39 to see the seal lions. It’s a touristy thing to do, sure, but c’mon, it’s crazy that there are just 100 or so seals lying out on the piers, flopping into the water. It’s one of those touristy things that you got to see.

4 p.m.: … Then order a fake Negroni (that’s still delicious)

Someone else told me that Marios’ Bohemian Cigar Store (566 Columbus Ave.) has a great negroni, and that’s what I was looking forward to. I don’t know if that person just misremembered, but they don’t even have Campari at Mario’s, or gin, so there’s definitely no negroni. But they did have a special cocktail called the “House Campari” that hit the spot. I liked it so much that I bugged the bartender for the recipe — turns out it’s Prosecco mixed with a few aperitifs. Mario’s also marks the first tourist T-shirt purchase of the trip.

7 p.m.: Eat tacos and duck into a famous dive bar

After checking into our hotel (we kept it simple and booked a room at the Inn at Union Square [440 Post St.], which was pretty affordable, clean, and centrally located, check, check, and check), we were ready for some good West Coast Mexican food. When I put out the bat signal for the trip, this fun (and cash only) spot Taquería El Farolito (multiple locations) was the place people recommended the most. I got carnitas, al pastor, and chorizo tacos, plus a Pacifico. But I think what most people get at this place are the burritos. I don’t regret getting the tacos, I just regret not getting a burrito.

Doc’s Clock (2417 Mission St.) is also in the Mission District and caught my eye because it has an iconic-looking neon sign. I guess the sign has a whole history — it got shut off for a while, and now it’s back on at the bar’s new location. It’s clearly a neighborhood institution. I’m a sucker for a local dive bar, and this fit the bill. Strange vibes, friendly people, cheap drinks, shuffleboard, cash only, loud music — you know the drill. It was great.

Day 2

11 a.m.: Pick up the rental car and head north

There was a Hertz rental spot a block away from the hotel, so I walked over there to pick up the car for the four-hour drive to Westport, an old coastal logging town deep in Mendocino County, where my girlfriend’s cousin was getting married. The drive was unreal, all of it breathtaking. The Golden Gate Bridge, hairpin turns through the mountains, wine country for miles and miles, redwood groves, cliffside roads on the edge of the Pacific Ocean. We took 128 to Highway 1, because going on the 1 the whole way takes much longer. This route takes you through the redwoods and then as soon as you get out of the forest, you end up right on the coast, with cliffs and the Pacific crashing into the shore. We stopped three or four times to take it in and snap a pic.

5 p.m.: Arrive in an old logging town

The couple getting married recommended the Westport Inn (37040 CA-1, Westport; 707-964-5135) for the weekend. (It’s still called the Lost Coast Inn on Google Maps, for some reason.) This was a really nice and cute hotel with a cabin vibe. Our room came with some snacks, wine glasses, water, a full tub, a TV, and Wi-Fi — which you’ll need if you want to work on your newsletter or browse Instagram because there’s no cell service in Westport. Make sure to take a look at the Westport Whale next door. It’s just a big sculpture of a whale that’s in someone’s yard.

6 p.m.: Head to dinner in Fort Bragg

We grabbed dinner at Los Gallitos (230 N Franklin St., Fort Bragg), this Mexican spot that was recommended by some locals. Big portions, charming interior, delicious drinks, and affordable prices, what more do you need. Great, now I’m craving their enchiladas.

Day 3

10 a.m.: Start the day with coffee, eggs, and gas-station sunglasses

The Westport Community Store is the only store in the entire town, and it doubles as the post office, liquor store, and single-pump gas station. It’s also where you can get a delicious microwaved egg sandwich and some coffee. (Pro tip: If you bring your coffee cup back, it’s only $0.89 for refills.) I highly recommend grabbing a bottle of wine here because it was probably made 20 minutes away in one of the most respected vineyards in the world. Another recommendation: gas-station sunglasses. Stop buying designer shades; you’re going to scratch them up or lose them. Just buy some scuzzed-out round-mirrored Y2K shades from a convenience store. This place had some great ones for $10.

Noon: Take in the scenery

Walk to the ocean. I sat on a log near a cliff for a long time just staring off at the incredible scenery while eating my microwaved breakfast sandwich. I don’t know if I’ve ever fully believed in a god, but after taking in that scenery for an hour, it’s hard not to walk away a spiritual man! This really was my favorite part of the whole trip. My mom has never been anywhere west of New York, so I FaceTimed her to share the moment.

3 p.m.: Attend a wedding (or make a pit stop) at an 1880s farmhouse

After a few hours of taking in the scenery, I went back to the inn and put on my chocolate cotton double-breasted suit from Stoffa and my Drake’s tie and walked over to Switzer Farm, where the wedding was being held. If you’re reading this, you may not be going to a wedding here, but it’s a lovely cliffside farmhouse built in 1884 that was once photographed by Ansel Adams.

Day 4

11 a.m.: Eat an omelet, sample mushroom ice cream

You know how you look through your parents’ old photos and some of them stick out as cool as hell? I wanted to take a photo like this to show our future kids, so I set a self-timer on my Contax T2 and took a photo of Jennie and me in front of the motel sign before hitting the road. Then we grabbed breakfast at Egghead’s Restaurant (326 N Main St., Fort Bragg), a kitschy Wizard of Oz–themed restaurant in Fort Bragg. You wouldn’t be able to tell from the name, but there are cute menu names like the Tin Man’s Heart for eggs. It’s family-run and was honestly really good. I got the Garlic Lovers Omelet, which was recommended to me by the chef. After that — and this is a crazy move — we went to Cowlick’s Ice Cream (250 N Main St., Fort Bragg) before splitting out of town. The wedding hosts recommended it, and they have some crazy flavors, like mushroom ice cream.

12 p.m.: Visit the Mendocino Coast Botanical Garden

This is a beautiful park full of plants and trails lining the ocean and some more really great views. I’m not a huge plant head, but this was beautiful to take in as a casual plant admirer. This also marked the second tourist T-shirt of the trip: a well-designed one with some mushrooms on it, basically everything Online Ceramics wants to be but found in a tiny town’s botanical-garden gift shop.

6 p.m.: Return to the Mission District

We wanted some Italian food for dinner, so we decided to hit Flour + Water (2401 Harrison St.), which came recommended by some friends of the newsletter. There was a wait, so we went over to Trick Dog (3010 20th St.), a cocktail bar a block away that was also recommended to us. I usually hate “cocktail bars” because they tend to be corny and try way too hard — especially a place like this, which has its menu laid out in categories like “Divinity” and “Creative Expression.” I ended up getting the Caballo Blanco, a fancy and fruity Mezcal drink with crushed ice. I wanted to hate it, but it was really good. Back to Flour + Water: This spot was incredible. It might have been the best meal of the trip. We started with Today’s Ricotta and Amberjack crudo, then got the rye pappardelle and a casoncelli dish with asparagus, walnuts, and brown butter, before finishing with chocolate budino.

Day 5

11 a.m. Wake up with pastries and matcha

We slept in a bit and went to Tartine Bakery (600 Guerrero St.) for breakfast, which was incredible. We got a chocolate croissant and a ham and cheese croissant. It was so, so, so good. Jennie loves matcha, so we went to Stonemill Matcha right around the corner. Matcha has always struck me as a kind of trendy VSCO-girl-era beverage, but I gotta say, this was great. I think the moral of the story here is that I should stop hating on things.

Noon: Go shopping

We went to Hayes Valley first and hit a few great shops, my favorite being Reliquary (544 Hayes St.), an upscale place with a nice mixture of old and new and cheap and expensive. I ended up copping a pair of baggy vintage-fit Japanese trousers made by Orslow. I wore the pants out of the store. Then we hopped on a bus to Haight Ashbury, where there’s obviously tons of great vintage shopping. The highlights were Wasteland (1660 Haight St.), Relic Vintage (1475 Haight St.), and Held Over (1543 Haight St.). Poking around the gift shops is worth it because there are some funny T-shirts and coffee mugs. There’s a seedy beach-pier-shop vibe to the stores there.

3 p.m.: Ride a Revel to the Japanese Tea Garden

We had a nice ride through the Golden Gate Park to the Japanese Tea Garden, which is the oldest public Japanese garden in the United States. It was about $10 to get in and a joy to walk around. It’s really beautifully preserved and filled with Japanese architecture, gates, and ponds with fish.

5 p.m.: Eat a pho-and-pupusa bang-bang dinner

Next we went to Phở Huỳnh Hiệp (1833 Irving St.), also known as Kevin’s Noodle House. I was a little skeptical of this recommendation because it’s a chain, even if it’s just two locations. And this was the most authentic and delicious pho I’ve ever had — the meat was flavorful, the broth was delicious, and a woman who seemed to own the place came over to us with a baby so the baby could smile at us. Jennie and I split a bowl and had some veggie spring rolls and peanut sauce to hold us over until Panchita’s Pupusería & Restaurant (3091 16th St.). Jennie and I love pupusas. So underrated and delicious. I got one spicy sausage and one spinach and cheese and washed it down with a Modelo.

8 p.m.: Drink wine at Bar Part Time

I’ve been a fan of these guys since before there was a bar (496 14th St.) to be a fan of, back when they were just slinging bottles of wine out of their cars and making killer merch. I wanted to say what’s up to one of the bar’s owners, Jeremy, who was a very early Perfectly Imperfect guest, but he had just gone home for the day. We hung out there for a long time and had a few glasses — a lot — of delicious wine before heading home for the night.

Day 6

11 a.m.: Pick up more pastries at Tartine

Yup, again.

Noon: Ride the trolly, visit a renowned bookstore

The Inn at Union Square is right next to the very tourist-y trolley (although in San Francisco they’re called cable cars), which is a great way to get to Chinatown without walking up the steepest hills you’ve ever seen. I actually really enjoyed the trolley ride. We went next to City Lights Booksellers & Publishers (261 Columbus Ave.), the country’s first all-paperback bookstore, which is located on Jack Kerouac Alley. I read On The Road in high school and nearly dropped everything to travel the country with my skateboard, but instead I became a programmer and ended up living in New York City. Anyway, at City Lights I bought a copy of Bud Smith’s Teenager, which landed on my radar after Forever magazine threw a party for it a few weeks prior. But what fully sold me on the book was the quote from the legendary musician Bill Callahan on the back. I read half of it on the flight home and loved every page. After that, we walked across the street to Vesuvio Cafe, a bar that’s filled with Allen Ginsberg and Kerouac memorabilia. They make a great negroni here, so I suggest ordering one and diving into whatever you just bought at City Lights. This place marked my third and final tourist T-shirt of the trip.

6 p.m.: Get a last martini-and-steak dinner

At Flour + Water, there were two chefs sitting next to us, talking shop, so I decided to butt in and ask for some recommendations. They both agreed that House of Prime Rib (1906 Van Ness Ave.) was a must-see, and it definitely was. It’s a place frozen in time, serving huge hunks of meat and shaking up perfect martinis. The wait was mad long, so I recommend sitting at the bar, having a few drinks, and chatting with the bartender. He was nice enough to inform us that Chuck Norris was sitting a few tables behind us. He offered to “take a picture of us” with a wink and then went into paparazzi mode and snapped a picture of Chuck.

8 p.m.: Drink the best Mai Tais ever

The last institution of the night, Tonga Room (950 Mason St.), is an underground tiki bar in the Fairmont Hotel, where it rains inside — like, actual water falling from the ceiling into the pool with thunder sound effects and flashing lightning. Did I mention there’s a floating barge with a live band on it? It’s like the Rainforest Cafe, if it had strong and delicious drinks — the best Mai Tais I’ve ever had, in fact. I definitely paid for it the next morning.

Tyler’s Northern California packing list

I rarely leave my apartment without my camera, especially when I’m traveling. Yeah, it’s a “trendy” camera, but I bought mine years ago when it was much cheaper than the current price ($1,300?! Please don’t spend that much; I got mine for $600). It’s just so much easier to lug this around compared to larger 35-mm. range finders, and it doesn’t sacrifice on quality at all because it’s packing very sharp Zeiss glass. I think I shot four rolls of Kodak Gold 200 in the short time we were there.

I like X-KD’s from Pacific Coast Sunglasses. They’re polarized and come in a wide variety of colors. If they get damaged or you drop them in a puddle near a urinal, it’s not going to break the bank to buy a fresh pair. I also highly recommend buying the wackiest sunglasses they have at the nearest gas station or CVS and wearing them for the whole trip.

I learned on this trip that Benadryl instantly makes me zonk out, which was megahelpful on the longish flights to and from New York. I took one shortly after boarding the plane, and I was fighting to keep my eyes open by the time the wheels left the ground. Am I allowed to recommend taking over-the-counter medication for things other than its intended use?

Photo: Courtesy the retailer

When you’re visiting this area of the country, I feel like it’s a good idea to dress in layers, since the temperature shifts from “kinda cold” to “kinda warm” pretty rapidly. I usually wore this jacket with some jeans and black oxfords and layered with a crew neck or T-shirt — is there a more classic look?

[Editor’s note: Bainbridge’s jacket is no longer for sale, but this similar style is available.]

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Six Days in San Francisco and Mendocino County