This has been a constant bucket list item for as long as I can remember, but I never actually thought it would happen. I imagine some of you are in the same boat. I was luckily at the mercy of my cousin (more on this below) who took it upon herself to plan & execute, so as anyone else would, I climbed aboard as fast as I could.

This was the first time in a while that I was 100% on vacation mode. Called in OOO and hopped on a plane to San Francisco. (If you’re on the fence about trying to swing this trip while doing remote work, I’d urge against it: not only will you be out of service for most of the trip, but it will also severely impact your day to day and make it almost impossible to indulge in the beauty around you.)

Quick reminders: Don’t miss the packing essentials linked at the bottom of this post! & check out the vlog of this trip here!

Last thing before I begin: it’s crucial I give full credit to my cousin, Eliza, for planning the majority of this trip herself. She will be running the Boston Marathon in October, 2021 and is raising money for Dana Farber (Cancer Research). If you plan to use this itinerary for your own trip, please consider donating (even just a few dollars) as a (surprise) thank you!

Day One:

• Fly from NYC —> San Francisco & meet up with 4 other girls.
• Uber to pick up camper van from Escape Camper Vans (Maverick size- we named him Wacky Wayne).
• Stop in San Francisco for lunch at Palms House (better option would’ve been Wildseed) 
• Drive to Santa Rosa, stop at Trader Joes for snacks/ quick dinner
• Pickish dinner at Airbnb (cheese, crackers, veggies) 
• Early night in watching “Wine Country” on Netflix

Day Two: (wine tasting) 

• Wake up, walk to get coffee @ local bakery
• Designated driver pick-up ($50/ hour + 20% tip ended up being around $400)
• Vineyard 1: Chateau St Jean
• Vineyard 2: Benzinger
• Vineyard 3: Viansa (our favorite)
• Dinner at Willi’s Seafood Raw Bar (note: there are multiple locations, double check with driver which location) 
• Chill/ early night in

Day Three:

• Wake up, walk/ run
• Clean up Airbnb, pack up, and leave
• Breakfast at Oxbow Market in Napa at Model Bakery (Oprah’s favorite!) 
• Walk around Napa town center 
• Get back in car and drive to Tahoe 
• Check into Airbnb
• Walk ~4 mi along Truckee River Trail
• Dinner at Bar of America

Day Four:

• Breakfast at Zuri Coffee Co,
• Rubicon Trail ($10.75 parking)- get there early ~7 AM, parking is very limited. 10 miles there & back (not a circle). Emerald Bay in the middle of hike.
• Swim & lay at beach where we parked 
• Lunch @ Sprouts 
• Walk to beach 
• Pull over at Emerald Bay lookout 
• Chambers Landing for drinks (Celeste) 
• Cards & Wine at Airbnb
• Ice cream, cheese & crackers, cards

Day Five:

• Check out of airbnb
• Brekky at Zuri Coffee Co.
• Drive –> SF
• Drop off belongings at Hotel Caza
• Lunch at Spark Social SF food trucks 
• Drive to Haight Ashbury (hippie history, good thrifting) 
• Walk to & around Lombard Street
• Walk through the marina & get drinks at The Interval (Long Now Foundation…) 
• Dinner at Greens 
• Post-dinner drinks at Balboa Cafe

Day Six:

• Early wake up 
• Drive to Carmel-by-the sea
• Coffee at the Carmel Coffeehouse (cute little seating outdoor area) 
• Walk to Carmel beach (cute, happy dog galore)
• Walked through Carmel neighborhoods
• Drive to Monterey
• Lunch at The Wild Plum Cafe (it was good but I’m sure there’s something better in the area? Maybe?)
• Walk around & chill at Atla bakery (This would have been the better option for lunch if you’re not too hungry)
• Wander through Antique Mall
• Drive back to SF 
• Takeout Chinese dinner @ hotel (lots of common areas at Hotel Caza) with childhood bff ❤
• Drinks @ Bus Stop bar (really fun, casual vibe with pool tables)

*note: we were doing a pick-up/ drop-off in Monterey but it would make more sense to do this trip once you leave SF so you can just continue on the southward route.

Day Seven:

• Wake up in San Francisco & check out of Hotel Caza
• Breakfast at Le Marais (croissant & mocha) 
• Head out of SF 
• Stop in Pfiffer State Park (Gorgeous beach. One of the trip highlights for me.)
• Lunch @ Big Sur Taphouse (Surprisingly great lunch spot with lots of outdoor seating, I got the impossible burger) 
• Stop in San Louis Obispo Trader Joe’s for camp food
• Drive to campsite + setup camp
• Sleep at camp/ in car

Day Eight:

• Wake up at campsite, pack up, and leave
• Drive to Hot Springs Hike (wouldn’t recommend)
• Drive to Santa Barbara
• Coffee & snacks at Handlebar Coffee Roasters
• Walk around, stop in EPIC antique store (this itself made the stop in SB worth it)
• Drive to Malibu
• Lay at Zuma Beach
• Drive into LA, check into Chamberlain Hotel (loved this hotel- super accommodating & great location)
• Dinner & drinks @ Melrose Umbrella Co.
• Went out at No Vacancy (really fun speakeasy- feels like you’re at a house party)

Day Nine:

• Alfred Coffee
• Hang at hotel pool
• Brunch w/ friends at Gracias Madre
• Walk around Melrose, pop into shops
• Hang w/ friends in Beverly Hills
• Waterfront Venice– drinks & dinner 
• Drinks & friends at Chulita (fun/ casual bar in Venice) 
• Went to The Lincoln (younger, more poppin’ bar)

Day Ten:

• Wake up & check out
• Head to Erewhon– stock up on juice, breakfast sandwich, lemon poppyseed muffin for plane ride
• Drop off Wayne in LA
• Fly from LAX –> NYC
• Head home 😦 

YOUR ROAD TRIP ESSENTIALS: