This is part of my remote work travel series where I review places I visit as a digital nomad. Check out the rest of my posts and follow me on Instagram, YouTube, Substack, or on TikTok for more travel content! This post contains affiliate links*, meaning I may make a small commission at no additional cost to you. Thanks for supporting my blog!

I’ll be honest, there’s something cursed about Oakland. Every time I’ve visited, I’ve felt this sense of doom. This isn’t even hyperbolic, in a city where gangs rove the streets for Teslas to break into so they can steal tech bro’s laptops and ransom company trade secrets, and the FAANG caste system douses the rest of the city in tax-abated deterioration. 

If you ever wondered how tax breaks could crush a city that houses some of the biggest companies in the world, SF is the right place to see this in action.

However, even with my distaste for SF, I did enjoy my time in Oakland, which has its own demons but is more palatable than San Fran due to the fact it’s surrounded by nature and also has some great vegan joints. These are redeemable factors in my book. Oakland gets a pass (for now.)

Where to Stay in Oakland, CA

We stayed in this gorgeous cottage atop a hill in Piedmont overlooking the Bay. I can’t recommend this charming cottage enough: it’s got a homey, cabin vibe and the view of the San Francisco skyline is superb. It also boasts a private garden that we would do yoga in or just sit outside and get some fresh air. My partner and I spent most of our time here watching the sunset from our dining room table. While not super walkable, it’s a great getaway and is a quick drive to hiking trails and great restaurants. 

There are a lot of pockets of Oakland, so I can’t recommend neighborhoods to you, really. But if you’re not staying somewhere scenic like where we were, stay somewhere within walking distance to restaurants and chic outdoor cycling gyms like RIDE Oakland. 

RELATED: The Best Travel Cards for Digital Nomads

What to Eat and What to Do in Oakland, CA

We didn’t *do* a whole lot in Oakland. We mainly went on walks on trails next to the bay, and then went on hikes on trails in the mountains, rinse and repeat. I’m headed to NYC for NFT NYC soon, so I wanted this Oakland stint to be restorative and chill, which it was for the most part. 

We did eat a ton of great vegan food, and here are our favorite spots: 

• Arizmendi. This is one of a few great pizza collective shops in Oakland (the other being the Cheeseboard Collective!) 

• Two Mammas Vegan Kitchen. I was trying to find a non-soy savory vegan option, and this place has a ~great~ florentine vegan option with sauce and an English muffin to die for. Great food here even if the area is a bit rundown. 

• Señor Sisig. Wow wow wow wow I still can’t get over how great this Mexican food was. The vegan “cheese” fries were awesome, and I loved the vegan crunchadilla. I didn’t realize how badly I was craving good Mexican food until I had this after a long hike. 

• Millennium. A great hearty, seasonal vegan place. I’ve heard good things about the tasting menu, but we were too full from getting vegan mozzarella sticks at the Butcher’s Son in Berkeley to go for it. My partner and I split a salad and the cauliflower steak here and it was a perfect amount of food.

We also went into SF for a Sandbox VR game and dinner at Nightbird, which was lovely, to celebrate my birthday (as I turned 28 this year!), both of which I can recommend. We did Nightbird’s tasting menu and it’s quite an affair, but fun to do with friends for a special occasion.

Tips for Digital Nomads Visiting Oakland

As of June 2022, mask mandates are back in place due to a COVID spike, so working in coffeeshops is still a no-go. NorCal is taking COVID more seriously than many of the other stops on our roadtrip, which is good for the city but generally not ideal for traveling digital nomads trying to find places to get work done.

That’s why it’s best to book an Airbnb with enough space to work from home. The weather is ever-changing, so finding an outdoor cafe is also not quite ideal for us remote workers who have a ton of Zoom meetings, so it’s key that you have a workspace in your accommodations.

End of Our Remote Work Roadtrip!

Aaaand that’s a wrap on our remote work roadtrip! It’s been two months of adventuring, Airbnb hopping, and vegan food tourism.

I love remote work because it helps slow the passage of time: I’m forced to take stock of my days, explore new cities, and experience different facets of life. 

I’m able to do my work from gorgeous locations. Whether that’s at the top of the Oakland mountains or in a hotel room balcony overlooking the Bellagio fountains in Vegas, I’ve had quite the backdrop to my writing so far. 

I’m a firm believer that remote work makes us better as writers and humans. It provides more inputs, more forms of art, different perspectives, and challenges us.

In short? Go book that next trip. It’s waiting for you.

If you’re looking to kickstart your remote work/digital nomad journey, check out my freelancing 101 free resource guide.

Happy travels!

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