Being from the East Coast, California has always allured me. Driving down the coast of California is a staple of bucket lists, country song lyrics, and GTA V gameplay. I turned a work conference into a two week trip – intent on making my own opinion about the divisive San Francisco, curious about the Palo Alto described in most CEO biographies published in the 2010s, prepared to cosplay Big Little Lies in Monterey, excited for what thoughts long hours of driving would yield, determined to get beach time in February, unaware of San Luis Obispo, unexpecting of Santa Barbara, and ready to hit a trade show floor in San Diego. This 15 day trip in February 2025 gave me a good taste of who I really am when I’m away from familiars and home.
If I don’t provide a recommend or skip it means it was neither good or bad. You’d be safe to explore for yourself but it’s not a “can’t miss”.
My takeaways from this trip:
- I would’ve loved living in San Francisco in college/right out of college
- The Chinese and Indian food in the Bay Area is no joke
- Driving in a two-door Mustang down the 1 is pretty cool, and so what if I took several pictures of that car at sunset
- I had mentally fostered a “California driving” playlist in my head for over a decade, but when the time came, I listened to a podcast about the NBA officiating scandal, Khalid’s debut album, Viva la Vida by Coldplay, and an assortment of old playlists that changed with every stop and start of the car.
- I’m not good at golf, but neither are the other tourists playing at Pebble Beach
- In my “retirement”, I should become an adjunct professor and live in San Luis Obispo
- An AirBnb with a host who lives there can be a total hit (Santa Barbara) and a total miss (Cambria)
- Touristy towns and cities are that for a reason. I’ll have some chance of finding a hidden gem in my own country and language, but most of the time I’ll be disappointed with a town that has a population of 18.
- I can make conversation with anyone, but I rarely will start it.
Day 1, Saturday:
- Start: DC | End: SF
- Flight from DCA to SFO
- Stay: Pickwick Hotel
- Do not recommend – loud, in need of repair. If I had to stay a night longer I would’ve gone somewhere else
- I didn’t know much about neighborhoods, but I thought Union Square would be geographically convenient for me
Day 2, Sunday:
- Start & End: SF
- Breakfast at Mellis Cafe
- Walk towards the Embarcadero, skip the Financial District (dead on a Sunday), cut through Chinatown
- Pier 39 to shop and watch sea lions
- Go to Musee Mecanique to play games for quarters
- Lunch at Nick’s Lighthouse
- Avoid the line at Boudin, be charmed by an overly eager waiter waving people off the street, and eat a bread bowl
- Drink at Standard Deviant Brewing to support a fundraiser for the opening of Rikki’s, a women’s sports bar
- Recommend. They had the Bay FC game on, there were tons of lesbians, and I felt like my Box2Box friends would go here
- Coffee and reading at Four Barrel Coffee
- Skippable
- Walk through the Mission District and Mission Dolores Park
- Grab a drink at Lost Resort with Aditi, one of Sean’s friends
- Recommend
- Tacos El Charos
- Recommend
- Street vendor with some tables. Felt euphoric about my Spanish speaking skills. Thank you Ritwik!
Day 3, Monday:
- Start & End: SF
- Walk through Union Square to Lafayette Park
- Brunch at 6 Tables
- Recommend, shakshuka
- Sam and Olivia happened to be in town!
- Go to Crissy Field East Beach for views of the Golden Gate Bridge (GGB)
- Go to the Palace of Fine Arts
- Recommend – this was one of the most stunning pieces of architecture I’ve seen
- Take the bus to the GGB Overlook
- Take the bus to Richmond
- Lunch at Ilana Coffee – bahn mi and Vietnamese iced coffee
- Walk and scooter through Golden Gate Park
- Recommend
- I did National AIDS Memorial Grove and Hippie Hill
- Take a Waymo back to hotel
- Dinner at Hang Ah Tea Room
- Recommend
- The best Chinese food I’ve had outside of China
Day 4, Tuesday:
- Start: SF | End: Miramar
- Breakfast at Mo’z Cafe
- Pick up rental car, relive the Seinfeld episode where the car reservation was not held, but end up with a two-door Mustang
- Drive over every bridge that connects to SF
- Golden Gate but fail to book a reservation for Muir Woods
- Richmond Bridge but give up on a plan to see redwoods
- Bay Bridge to head to Miramar
- Lunch: homemade peanut butter and banana sandwich
- Head to JV Fitzgerald Marine Reserve
- Skip, at least in February
- Walk along Half Moon May Coastal Trail
- Dinner at It’s Italia
- Recommend
- Stay at Airbnb in Miramar
Day 5, Wednesday:
- Start: Miramar | End: Santa Cruz (good mid-point between Miramar and Monterrey)
- Drive to Upper Crystal Springs Reservoir Vista Point for an overlook
- Hike Purisma Creek Redwoods (out and back), about 2 hours
- Recommend – I got to see my redwoods!
- Lunch at Chef Chu’s in Los Altos
- Recommend – hot and sour soup
- The entire Chu family works at the long-estalbish Chinese restaurant, except the black sheep son. Jon Chu, director of Crazy Rich Asians and Wicked, is the black sheep.
- Thank you JMB!
- Visit the Computer History Museum
- Skippable
- Drive to Stanford
- Get coffee and finish the latest Fourth Wing book at Philz in University South
- Recommend (and bring this chain back to DC!)
- Explore Stanford University, including Chanel Miller’s garden
- Dinner at Darbar
- Recommend, and don’t skip the mango lassi! This was one of my favorite meals of the year
- Drive to Santa Cruz
- Stay at Rio Vista Inn & Suite in Santa Cruz
- It’s like a B&B and it was fine, but as discovered the next day, I don’t recommend Santa Cruz. I went there because driving to Monterey was too far. I only knew Santa Cruz from the skating brand and a vague romanticization of California surfing culture.My guess is this was a cool place in 80s and has become rundown and forgotten while the Bay Area and SoCal have continued to blow up.
Day 6, Thursday:
- Start: Santa Cruz | End: Carmel
- Breakfast at Firefly Coffee House
- Walk along Santa Cruz Boardwalk
- Drive to Monterey
- Go to Monterey Aquarium
- Recommend – the $80 price tag is worth it to see puffins, penguins, jellyfish, kelp forests, and sharks
- Homemade sandwich for lunch
- Walk between Lover’s Point Park and Kissing Rock View Point
- Drive 17 Mile Drive
- Play pitch & putt at the Hay, one of the courses at Pebble Beach
- If you’ve never heard of Pitch and Putt, the holes are significantly shorter, often under 100 yards, in a 9- or 18-hole format.
- Listen to the sunset bagpipes at The Links at Spanish Bay
- Dinner at Alvarado Street Brewery and Bistro
- Recommend
- Stay at Carmel Green Lantern Inn
- Recommend if you’re comfortable with not a lot of space and want whimsy
- Referral link: https://www.airbnb.com/rooms/49004800?guests=1&c=.pi129.pkpast_trip_share_virality&s=67&unique_share_id=209d928f-c30d-4bd1-b7e3-7c8f080efaaf
Day 7, Friday:
- Start: Carmel | End: Cambria (mid-point driving down the Pacific Coast Highway)
- Go to the Carmel Mission Basilica, one of the earliest Catholic buildings in California
- Skippable unless you’re passionate about Catholicism and its history in Mexico/the US
- Talk a walk at Point Lobos State Natural Reserve
- Drive to Cambia by the 101 (Big Sur was closed)
- Lunch: Woody’s at Del Mesa
- I can’t imagine this makes many PCH itineraries, given that it’s a restaurant in a 55+ community, but I had a great meal
- Odonata Winery
- Arrive in Cambia
- Dinner: Las Cambritas
- Big marg, chips & salsa, fajitas
- Stay at Airbnb
- The host lives in the house and you stay in the lower level. She cooked and we had breakfast together every day. We talked about her life in California, which frankly was a bit disheartening. Wasn’t my thing but might be for someone else! I regretted having 2 nights in Cambria, because there wasn’t much to do
- Referral link: https://www.airbnb.com/trips/v1/1663715930879500171
Day 8, Saturday:
- Start & end: Cambria
- Hearst Castle – Grand Rooms Tour
- Big recommendation! I nearly had a private tour
- Elephant Seal Vista Point
- Preferred the San Francisco one
- Lunch: Moonstone Beach Bar & Grill
- Skippable
- Visit Harmony (population: 18)
- Skippable
- It’s just small gardens, an ice cream truck, glassworks, and a pottery store
- Snack at Linn’s Easy as Pie Cafe
- Recommend
- Sunset at Morro Bay
- Recommend, I should’ve spent more time here
- Stay in Cambria
Day 9, Sunday:
- Start: Cambria | End: Santa Barbara
- Drive to San Luis Obispo on my friend Melia’s recommendation
- I should’ve made Cambria an afternoon stop and made SLO an overnight
- Walk through the Botanical Garden
- Lunch: Efren’s San Luis Obipso
- I don’t think the torta was the right thing to order (they’re also the size of my head), but I think the food is good
- San Luis Obispo Museum of Art
- Go thrifting
- Coffee: BlackHorse
- Recommend
- Drive to Santa Barbara
- Dinner: DoorDash Sushi Gogo
- Recommend
- Stay at Airbnb in Santa Barbara
- Recommend 10/10
- This was the opposite experience to Cambria. The family lived in the house with 2 small studio cottages in the back, one of which I had to myself. It was one of the most beautiful backyards I’ve seen, full of lemon trees and a gurgling fountain.
- Referral link: https://www.airbnb.com/trips/v1/1663719546702326769
Day 10, Monday:
- Start & end: Santa Barbara
- Work remotely from the Santa Barbara house
- Lunch: Boathouse at Hendry’s Beach
- Recommend (thank you Nadia)
- Walk West Beach to Ledbetter Beach
- Dinner: Lucky Penny at the Funk Zone
- Recommend
- Super cool area with a bunch of bars and restaurants; would be good with friends
- Get a drink at Test Pilot
- Skippable
- Stay in Santa Barbara
Day 11, Tuesday:
- Start: Santa Barbara | End: San Diego
- Work remotely from Santa Barbara house
- Client Lunch: Reunion Kitchen + Drink
- Recommend
- Remember how I added PTO to a SoCal work trip?
- Coffee: Lighthouse Coffee
- Drive to San Diego and get stuck in LA traffic for 2 hours
- Dinner: DoorDash Urban Indian Cafe
- Stay: Porto Vista Hotel
- Skip
- Little Italy neighborhood
Day 12, Wednesday:
- Start & end: San Diego
- Work remotely from the hotel early AM
- Coffee: Influx Cafe Little Italy
- Skippable
- Go to trade show at Convention Center
- Spontaneously go to the USWNT game vs. Japan with Evelyn
- Stay in San Diego
Day 13, Thursday:
- Start and end: San Diego
- Work at hotel and at trade show
- Lunch: The Taco Stand, North Park
- Recommend, thank you Melia
- Explore North Park – Verbatim Books, farmers market
- Get a drink and read book at Bivouac Ciderworks
- Explore the Harborview
- Dinner: Civico 1845
- Stay in San Diego
Day 14, Friday:
- Start & end: San Diego
- Work from hotel
- Client lunch: Ballast Point Brewing
- Explore Hillcrest
- Coffee: Better Buzz Coffee Hillcrest
- Recommend
- Get picked up by my friend Melia and drive to La Jolla
- Drinks: La Valencia Hotel
- Recommend
- Dinner: Puesto Lo Jolla
- Recommend
- Stay in San Diego
Day 15, Saturday:
- Start: SD | End: DC
- Fly SAN to IAD
- There’s nothing more to it. Two weeks alone in California, experiencing San Francisco and San Diego, and stopping by almost everything in between (sorry LA, you were too much of a behemoth for this trip) had come to a close
Trip Influences
Book: Know My Name
- Leti and I agree that Chanel Miller’s biography should be required reading for every college freshman. You probably know the name Brock Turner. It’s likely you don’t the name of the survivor of his court case. Her memoir is one of the best books I’ve read. She was a student at Stanford, failed by the university, but ultimately got a garden built by the scene of her assault to turn something horrible into something peaceful.
Book: Onxy Storm
- I’m not above reading fantasy smut!
Book: The Four Winds
- I spend lots of hours driving listening to this audiobook, but frankly I couldn’t stand it and gave up once I came back.
Podcast: Whistleblower
- The story of an NBA gambling scandal that ultimately led to a guilty plea by referee Tim Donaghy. The gambling scandal has continued with additonal arrests of players in 2025.
Podcast: Desert Island Discs: Harriet Wistrich, lawyer
- I’m an occasional listener to this podcast, but I’m often moved when I do. This is a long running series in the UK that dates back to 1942. Guests are often at the top of their field, whether well-known celebrities like Adele or Cillian Murphy, or gardeners and computer scientists. Guests are asked to give a playlist of 8 songs they would listen to if they were stranded on a desert island and often tell the story of their life while doing so. I often cry at songs dedicated to deceased lead ones or regain some hope in humanity. Harriet Wistrich is a human rights lawyer who also happens to be queer 🙂 I listened to this episode walking along the coast in Miramar.
TV Show: Big Little Lies
- If you haven’t watched this and need an excuse to, here it is. Whodunnit story with the vibes of a high-stress PTA meeting featuring ocean breeze… what could be better?
Video: Super Showcase Spokesmodels
- I was constantly saying “Pebble Beach” like Kristen Wiig and Maya Rudolph in this SNL sketch
Music: Spotify playlist by Slasher, “Only Songs About San Francisco” (link)


























































































