Updated: May 26, 2021
How to Access This Itinerary
Download the Roadtrippers app and click the link here to open the You're the Only Highway 1 For Me itinerary. Below you will find more detail about the stops and where to stay in each city. This trip will take you for two weeks up the coast of California, working during the week and traveling on the weekends. Make sure to check out our post 10 Things To Know Before Your Work From The Road Trip before you start!
As always, reach out over Instagram DM via @PollenTravels for any help you may need and know you can always purchase a Custom Itinerary on the shop page!
Weekend 1- Ventura
For the first weekend, home base will be Ventura, CA. The perfect mix of sleepy beach town and funky activity hub, it is one of my all time favorite cities in California. Ventura is 1 hour from LAX. You can rent a car to get from LAX and rent bikes at Ventura Bike Rentals. A beach cruiser will do the job just fine for $60 a day. If you stay at Waypoint (see below), bikes are included.
Accommodation In Ventura
I recommend Waypoint Ventura ($165). Waypoint is a vintage trailer hotel aka a funky parking lot full of refabbed Airstream trailers! Use the complementary bikes and fire pits and meet fellow travelers! Note that this place doesn't have reliable WiFi for Zoom calls, but if you can be more offline for the weekend it's worth it.
If you do need a good work setup, these three places have been confirmed to be great work spots by their owners!
Ventura Beach Retreat $156 Tech folks lived there for a few months and worked remotely over Zoom.
Cottage at Pierpont Beach $148 Wifi is confirmed strong enough for remote working over Zoom.
SWELL Studio $149 Able to run Zoom calls without interruption with high speed Spectrum wifi.
Weekend 1, Day 1- Los Angeles Highlights
Studio Tour and Lunch
You just flew into LAX- what now? If you can get there in the morning, use the day to explore some classic LA spots. Start off the day with a morning studio tour. Choose from Sony, Warner Bro's, Paramount and more based on the shows you love (Note: Sony is only 20 minutes from the airport). Next, grab lunch at The Original Farmer's Market where you can find lots of different food stalls for choices for the whole group!
Hollywood Sign Hike
It's time to get a little exercise, so let's make it classic LA and go for a hike to see the Hollywood sign! While there is a 6.5 mile loop that takes you behind the sign, for a much easier 2.5 mile jaunt on Mt. Hollywood Hiking Trail you can see a slightly cockeyed view of the sign and get some nice views of the city. Just park at the Griffith Observatory Parking Lot and follow signs for the Mt. Hollywood Hiking Trail at the north end of the lot.
Hollywood Walk of Fame
No LA trip is complete without walking down the Hollywood Walk of Fame and seeing the names of your favorite stars in the sidewalk. If you're looking for someone specific, look them up on the official website's Star Map.
Note: Apricot Lane Farms, the subject of the award winning documentary "Biggest Little Farm" is also in the area as an alternative to LA highlights. It is closed for COVID-19 indefinitely right now, but normally for $35 you can take a 2 hour tour through the farm and experience a really fascinating small farm in action. Keep checking back to see if it has opened yet!
Dinner and Drinks in Ventura
It's time to check in to your hotel in Ventura, so put on your road trip playlist and make the 1 hour drive up the coast.
Once you've checked in to Waypoint or your chosen accommodation, if it's getting close to dinner time, walk or bike to the Ventura Pier and grab some fish tacos at Beach House Tacos and a beer next door at Madewest Brewery. Bring your food and drinks to the picnic tables on the pier to watch the sunset surf. Just make sure to bundle up, it gets chilly when the sun goes down. If you're still feeling frisky, bike or drive downtown to VenTiki, a teensy tiki bar on Main Street.
Weekend 1, Day 2 - Surfing Ventura or Downtown Shopping
Coffee and Sunrise at Surfer's Point
Get up before the sun rises, make some coffee and bike or walk down the Promenade to Surfer's Point to watch the many surfers roll in the waves as the sun comes up. Trust me, it's worth it- just bundle up in layers!
If you feel up for getting your own feet wet, contact Mary Osbourne's surfing camp and set up a surf lesson- board and wetsuit included! Surfer's Point, or C Street as the surfers call it, is a great spot for beginners to learn, with gentle waves, shallow water and gorgeous scenery.
Mary Osbourne Surf ~$120 for 2 hour session
Downtown Shopping & Farmer's Market
If you're not looking to surf, head downtown for the day and explore Main Street. Most shops and restaurants are local around Ventura. My favorite shops are Passport Habits, Findings Market, Ikat and Pearls and the little local used bookshop Calico Cat. Patagonia's flagship store, where Yvon Chouinard first started selling stand up shorts and climbing equipment, is now a beautiful retail shop in the area. If you're shopping on a budget, just down the street is Real Cheap Sports- same stuff lower prices.
On Saturdays you'll see the farmer's market right next to Main Street, a 15 minute walk from Waypoint or 5 minute bike. Visit for hyper-local strawberries, tender greens and citrus, but make sure you get there early- it's only open from 8:30-noon.
If you feel like splurging for a lunch out, get an Italian sandwich at Peirano's and sit outside on the fountain across the street from Mission San Buena Ventura. You can also take a self-guided tour of the historic Mission and its gardens for just 5 bucks!
Dinner at Himalaya Nepalese Restaurant
In the evening, bike or drive to Himalaya Restaurant, a Nepalese/Tibetan restaurant. Sit on the floor and experience this unexpected cuisine.
Evening Drive-in Concert
During the pandemic, there were near-nightly drive-in theater happenings at the fairgrounds through Concerts In Your Car. Look up what's on the agenda and sing along over the radio to a screening of Mama Mia or rock out on your tailgate to a country artist. BYOB! Tickets range from $30-$150 per car.
Weekend 1, Day 3- Ojai & Solvang, relocate to SLO
Exploring Art City
Pack your car in the morning to hit the road, but before you head out of town, stop and take a walk through Art City (10-5 Wed-Sun). Art City is an outdoor stone sculpture artists collective. Basically you walk around and can see artists creating sculptures out of stone and also visit a little indoor gallery on site to see some 2D artwork. Once you're done, hop back in the car and drive 20 minutes to Ojai!
Lunch & Exploring Ojai
Have brunch or lunch at The Nest, a healthy eats outdoor patio spot. They have yummy hard kombucha and cocktails as well. Explore the super unique outdoor bookstore Bart's Books and pop into a nearby art gallery or two. Bike over to explore the grounds of the rustic-luxe Ojai Valley Inn. The grounds are incredible, with giant old trees and rolling hilltop viewpoints and is definitely worth a visit on your way out of town.
Dutch City Solvang & Ostrichland
Then drive an hour and a half to Solvang, a Denmark themed city. Take a photo in front of the windmill downtown and pop in a shop or two. Once you've finished exploring, it's on to Ostritchland just down the road. This is one of the most hilarious experiences I've had on a road trip. The fact that there are ostriches roaming the countryside of California, and just the sheer number of them flapping and sprinting around, cracked me up. Be warned, they look like dinosaurs up close and very aggressively eat out of the little bucket that's a few inches from your hand. The best part- it's only $5 admission and $1 for feeding.
Drive to San Luis Obispo
It's an hour to drive to SLO, or 1.5 hours if you want to stay on The 1 exclusively. However this stretch of road isn't on the coast anyway, so I recommend turning on a podcast or downloading HearHere to listen to stories about the places you're driving by and cruise.
Week 1- San Luis Obispo
It may be time to work, but that doesn't mean you still can't have fun- that's the beauty of working from the road trip! San Luis Obispo, or SLO, is a laid back California college town. With the mission, Cal Poly, hot springs nearby and amazing hiking and beaches, it's a great spot to get work done and also enjoy a really classic Southern California experience during your after work hours.
Once you've made it to town, check in to your hotel or AirBnB. Below are a few I've vetted to make sure the WiFi is strong enough to work all week on.
Accommodation in San Luis Obispo
The Cottage at Old Morro $174- kids use the WiFi for distance learning so definitely strong enough!
Black Barn Ranch $273- have had many guests work from there, great wifi strong enough for Zoom calls.
Or find a chain hotel with credit card or hotel reward points
After Work Adventures in San Luis Obispo
Stay motivated to get your work done by planning to check out one of the below after work adventures! Don't miss the Thursday evening street fair or a night soak in the local hot springs, and if you're feeling energetic, maybe even squeeze in a sunrise hike to Bishop Peak! See below for more ideas, links, times and costs.
Evening farmer's market downtown (more like a street fair), Thursdays 6-9pm. Starting May 6 it will be reopening after being closed due to COVID.
Sunrise hike- Bishop Peak 2 hours
Walk the gardens at the mission (the museum and tours are closed due to COIVD)
Sunset Drive-In Theater 7 days a week, 8 and 10pm showings, $10 per adult, cash only. Box office opens at 7:30
Sycamore Mineral Springs- High end resort. Book a hot tub for $19 an hour. Open 9:30am-11:45pm
Avila Hot Springs- 100 year old classic hot springs group soak tub and pool. Sundowner Swim & Soak $8 after 5pm. Open 8am-9pm
Monarch Butterfly Grove (October-February) Free walk
Walk around Cal Poly’s campus
Hearst Castle Grand Rooms tour for $25, open 8am-6pm. (45 min away, closed due to COVID but keep checking back for more info!)
Eating and Drinking in San Luis Obispo
To save money, I recommend going to the grocery store and getting coffee, breakfast, lunch and snack food, but food and drinks are a big part of travel, so if you're interested below are a few bars, coffee shops and the most popular eateries in town.
Hotel SLO rooftop bar
Kruezberg German Coffee Shop
Scout Coffee, smaller but cute
Weekend 2, Day 1 - SLO to Santa Cruz
It's about to get awesome. The drive from SLO to Santa Cruz is truly epic, with amazing views on Highway 1 and way too many can't-miss stops along the way. That's why Day 1 is just one big awesome California road trip.
Accommodation in Santa Cruz
You'll be staying in Santa Cruz this evening, so here are some recommended places to stay:
West Cliff Hideaway $114 Super fast WiFi, recommended for working from home
Walk to the Beach and Boardwalk $148 Great location and plenty of space with strong WiFi
Ocean Pacific Lodge ~$165- Hotels are pricey in the area and fluctuate depending on the time of year but this lodge is only a 12 minute walk to the action and is reasonable
Drive Up The Coast on Highway 1
It's about 2 hours to get from San Luis to Big Sur, the next exciting spot. This is a classic stretch of Highway 1, so take your time driving, stopping at whatever looks beautiful. I recommend using the Roadtrippers app to easily see what you'll be driving past. One of those things is the Elephant Seal Rookery where you can see literally hundreds of Elephant Seals chilling on the beach below.
Short Hike to McWay Falls
Once you've made it to Big Sur, be sure to take the short trail to McWay Falls. It's only a mile round trip but the view is gorgeous. If you feel like stretching your legs more, check out Buzzard's Roost trail, a very popular 2.6 mile loop.
Drive through 17 Mile Drive in Monterey
An insanely gorgeous drive through Pebble Beach's 17 Mile Drive is absolutely worth the $10 entrance fee. You'll see rare Cyprus trees, rugged coastline and beautiful homes. You can stop and have lunch at one of the restaurants there too! Make sure you stop and take a photo of Bixby Bridge while on your way there, though. It's an iconic bridge used in many tv shows, including Big Little Lies.
Visit The Mystery Spot, Redwoods, and Surfers in Santa Cruz
You'll stop for the night in Santa Cruz, but there's so much to see and do there so make sure you give yourself lots of time to explore. I found Santa Cruz to be the friendliest town on the coast during my trips, and while it's very beautiful, it's also very goofy. One highlight is The Mystery Spot, a mysterious gravity defying area in the woods... Make sure you buy the $8 tickets in advance though, this place gets packed out!
Another wacky stop is the Bigfoot Discovery Museum. For a $2-$5 donation, you can learn all about bigfoot and see artifacts and videos of sightings in the area. Are you a believer?
Lastly, Santa Cruz has one more treasure trove- the giant redwood forests surrounding town. Take a walk through the Henry Cowell Redwoods along the Redwood Grove Loop Trail that's about a mile in total. These trees take my breath away, and walking through the groves with your eyes to the sky is something you absolutely can't miss.
Back in town, you can watch the surfers at Steamer Lane or pop in to a winery and do a tasting of local wine. If you're a Patagonia lover, there's at Patagonia outlet in town too, one of only 6 in existence around the world!
Weekend 2, Day 2 - San Francisco
Visit the Winchester Mystery House
If there's anything you missed in Santa Cruz, you can check it out this morning. Once you do get on your way to San Francisco, stop by the Winchester Mystery House and tour this never-ending mansion for $42. Sarah Winchester, wife of the founder of the company that made Winchester rifles, started a strange home renovation when her husband and child passed away that didn't stop until she died. Hallways that go to nowhere, doors that open to nothing, and stairs that never stop are just some of the things you'll see in this kooky house that was left behind.
Take a GoCar Tour of San Francisco
Drive in to San Francisco and head to the GoCar rental office in Fisherman's Wharf. This is a super silly self-driving tour in 3-wheeled, bright yellow audio-tour enabled go-carts. Stop when you want, listen to the audio telling you what you're looking at and see a ton of SF in 4 hours. There are lots of tour options but I recommend the 4 hour GoCar tour. It's a bit pricey at $210 for the four hours, but this one will get you to the biggest highlights of the city for the best price. I've always purchased a cheaper option through Groupon as well so make sure to check that. I guarantee you will feel silly but also have a blast, and anything you thought was cool you can go back and visit this coming week after work!
Week 2 - San Francisco
Accommodation in San Francisco
Secret Street In The Center of the City $150- In Nob Hill. Host reported super fast WiFi using mesh router
Bright, Modern Garden Unit $150- In Lower Haight. Guests report "immaculate" WiFi and host confirmed no complaints about WiFi strength from any guests
SF Garden Studio $128- In Marina District. Guests report strong WiFi. Small space but walkable to The Presidio and popular Marina district.
After Work Adventures in San Francisco
Walk across the Golden Gate Bridge
Picnic in Mission Dolores Park
Take the ferry to Sausalito for dinner and drinks at The Spinnaker on the water
Visit The Painted Ladies
Visit Alcatraz- $41. Note the last boat leaves at 3pm so you would need to skip out of work a little early for this adventure
Walk/Run/Bike in Golden Gate Park. Bike rentals in the park from ParkWide
Eating and Drinking in San Francisco
The Tonga Room- unique Tiki lounge
El Techo- rooftop Mexican food
Foreign Cinema- plays old movies in courtyard
Fig & Thistle - cute little wine bar
Vive La Tarte - tasty bakery and lunch spot
Noosh- Mediterranean casual lunch and dinner spot
Souvla- local greek chain lunch spot
Weekend 3- Day 1- Wine Country
As you go progressively north of San Francisco, there is less development but more beautiful landscapes to enjoy. This weekend will be a road trip north taking your time and then a quick 4 hour drive return to SFO on Sunday. The first night you end up in Mendocino.
Accommodation in Mendocino
Mendocino is quintessential northern coast. It's sleepy art haven with galleries, cute shops and coffee spots and lovely hikes in the area.
The Didjeridoo Water Tower Room $175- A funky stay, WiFi reported to only be in the common room and not in bedrooms. Note there are very few places to stay in Mendocino for one night only
Ocean Views in Mendocino $225- The only other one-night stay option in Mendocino. Reported great wifi by guests and amazing location if you're ok with the price!
Sonoma Wine Tasting
Saturday is wine country day! Drive across the Golden Gate Bridge into Marin County and head north about an hour to hit Sonoma. If there are wineries in Napa you are dead set on seeing, you can drive another 40 minutes northeast but in my experience Sonoma has just as much charm with less crowds and closer to the Highway 1 route.