How to Travel Without Leaving Your City

How to Travel Without Leaving Your City

I’ve spent a good portion of the last decade trying to build a design business that would allow me to live and work from anywhere. As life would have it, right when my business was finally at a point where I could travel with it, I met an amazing human who had a career that needed him to stay in one place. Of course. So what do we do when life doesn’t work out exactly the way we want it to? We come up with a new plan! That new plan for us was moving our lives from Austin to San Francisco for Kyle’s work.

In nervous anticipation of entering the dreadful Bay Area rental market, we decided to book a few Airbnbs to stay in while we looked for a place. When we realized that we were actually more excited about staying in the Airbnbs than we were about finding an apartment, we thought, “Let’s just live out of Airbnbs!” And just like that, we became nomads with jobs. Travelers within one city.

While living out of Airbnb for a year has been our way of finding an amazing balance between freedom and stability, it’s certainly not the only way. Even though we have no lease, no utilities, and no landlord, those kind of things aren’t what defines us as travelers. It’s our mobility and desire for adventure – two things that, when adopted, can make any office-working, home-owning freedom fighter feel like a nomad.

So how can you feel like you’re traveling without leaving your city?

Work From a New Cafe At Least Once a Week

Even remote workers fall into a daily work routine. When we find places that have reliable internet, good coffee, and plenty of outlets, we become regulars, and in doing so, end up trying new places less and less. With websites like this very one that you’re on (wink!) you can explore new places to work all around your city, and sort out the internet speed, coffee, and availability of electrical outlets all in advance.

Get a ClassPass Membership

A monthly membership to ClassPass gives you access to thousands of fitness studios all around your city. So instead of just doing the same workout at the same gym every day, you can try yoga, pilates, cycling, and so much more all within one week! The best part about it is that ClassPass encourages adventure by only allowing their users to attend each studio a maximum of three times per month. If you’re a routine-person, than that probably sounds annoying, but if you’re open to bringing a little adventure into your life, then it’s the perfect place to start.

Use Instagram for Research

I’m a visual person. When I’m trying to find new places to eat, events to attend, or things to do, I want to see pictures of what I’m getting myself into before I make the commitment. For that reason, Instagram is my go-to for preliminary travel research. Depending on what I’m looking for, I’ll do a couple of hashtag searches and see what’s popular. For example, “#travelsf” is going to show you a lot of people riding trolley cars and making out in front of the Golden Gate Bridge. Something more neighborhood-specific like “#hayesvalley” is going to show you a more local perspective of what to do and where to eat in the Hayes Valley neighborhood in San Francisco.

I’d also recommend finding a couple of local bloggers to follow, so you can see where they eat and what they do for fun. Bloggers love photographing food and bicycles and I love eating food and riding bicycles, so for me, it’s a foolproof recipe for success.

Create Fun Challenges and Quests

A great way to explore unchartered territory is to make it into a mission or challenge. For example, I would like to explore the Mission here in San Francisco by attempting to find the best burrito in the neighborhood. How do I do that exactly? By eating all of the burritos and then deciding from there. Obviously this isn’t something that can be accomplished in one weekend (I’m good, but I’m not that good), but it’s an ongoing activity, an excuse to visit the Mission, and a reason for me to always be trying a new burrito joint!

Find a Social Bike Ride (or Create Your Own!)

Bikes are the absolute best way to see a city and social cycling is so much fun. I’m not talking about dudes riding bikes in kits and $7,000 road bikes. I’m talking about people from all walks of life on all different kinds of bikes, drinking beer, tea, or whatever, all going on full-on cycling adventures through their cities.

If you live in a city with organized social cycling events, join their Facebook groups and newsletters so you can hear all about the rides. If your city doesn’t have an organized social cycling scene, create your own! Get some friends together and do a local brewery tour by bike, or ride to a local park to do some yoga and then finish up the ride at a local coffee shop. Get creative and remember to follow general social cycling rules – ride with traffic, not against it.

These are just a few ways you can feel like a nomad without leaving your city, but there are so many more. Try a new restaurant every Sunday, get an Airbnb for a weekend in a neighborhood that you have yet to explore, attend a new festival… The key to bringing a nomadic feel to any routine lifestyle isn’t to not have a lease or an office job. It’s to look at every aspect of your day and think, “is there an opportunity for adventure here?” If the answer is yes, than carpe diem.

This was originally published as a guest post for’s blog, an online community of people and places helping one another find and share spaces to work remotely all over the world.

Airbnb travel for a year

Austin to San Francisco: The Journey Begins

Moving to San Francisco has been something that I’ve thought about since I first started working in the tech industry. When my employer, Bigcommerce, opened an office in the Bay Area last year, I was pretty excited. I had the chance to go out and visit, and was even able to bring Emily along with me. As I’d predicted, she fell in love with SF during that week she spent with me living in a hotel in the Financial District a few blocks away from the Bigcommerce office. Thus began our plans to move to the Bay.

Knowing that I had a job to move to already really made things a lot easier for both of us. Initially, we planned to move, stay in short term housing for a short period, and then move into a more permanent space. Little did we know what we were getting ourselves into with the housing market in San Francisco. Quickly it became pretty obvious to both of us that finding a home was going to be a daunting task for two people who just showed up in the city.

At the same time we (mostly Emily) were doing research into where in the Bay Area we wanted to live, and could afford. We discovered that unlike Austin, San Francisco is a much more complicated place. There are what seems like hundreds of neighborhoods, and each one seems to be unique and different from it’s neighbors. With so many differing opinions on the neighborhoods and rent prices, we wanted to make sure we make the best decision possible for our first time around.

One day, about a month before we were set to leave Austin, we stumbled on what seemed like a loophole on Airbnb: renting for 28+ days in a row meant that we would have to pay a significantly smaller short-term occupancy tax. This made month long rentals at Airbnb properties fairly affordable, so we ended up booking a one month long stay along with our two one week stays that we had already booked. We initially reasoned that a month and a half of time in temporary housing, would be plenty of time to find a home. But as moving anxiety mounted, we considered extending the stay to another Airbnb in a different neighborhood for another month. Which is where we hit on an idea by accident, what if we lived in Airbnb’s for an entire year?

At first, the idea seemed crazy. Who’d want to live in someone else’s house for an entire year, and even more, who’d want to move every month to a new location? Would we get tired of having no personal space? Would we be able to live out of just a couple suitcases for a whole year in a city where we’re working and living otherwise normal lives? We came to the conclusion that we both like to live our lives as simply as we can, and if this project does one thing for us, it will encourage that lifestyle even more. We also both enjoy traveling and experiencing new things, so we’re confident that we can move once per month to a new space without getting too tired of it. So yea, we decided to commit to this crazy idea and have some fun with it.

Right off the bat, we found lots of places we wanted to stay, so we started booking. Before we knew it, we had out rent paid until June! That was a pretty cool feeling, not to have to worry about paying for a place to stay for around 6 months. The biggest benefit to our new plan, was that we’d get to try out every neighborhood that we were interested in. This way, when it comes time for us to get a real place, we’ll have experienced a good portion of the city and be able to make decisions based on what we actually know about a neighborhood, and not what we’ve heard from other people. We also realized from talking with friends, and from reading online resources, that a lot of the good apartments in San Francisco aren’t even on Craigslist, but are advertised using signs or good old word of mouth. Being in the city for a year before settling down will allow us to figure out if this is indeed the case, and if it is, it’ll let us find some of those little spots that we would have maybe not found on the internet.

Getting out to San Francisco was the next big hurdle. We felt that driving ourselves to California would be the best way to ease the transition out of Texas and into a totally different environment. It’d give us the opportunity to drive through Arizona and Southern California to visit with my family, and stop in Joshua Tree National Park and White Sands, New Mexico, two stops on Emily’s list.

We’ll be driving our U-Haul, across half the country together, and plan to take four days to make the 1,976 mile trip. We’ll spend the night in White Sands National Monument the first night, so we can wake up the next morning and have our coffee here:

White Sands National Monument


The next night will be spent in Phoenix, Arizona, then we’re on to Joshua Tree National Park for lunch and then to Ventura, California where we’ve got an Airbnb bungalow right around the corner from the beach. The last day will bring us right up the coast and into San Francisco where we’re heading to Oakland for our first official Airbnb stay of our trip.

All in all, both of us are very excited and ready for the big change in our life. We love that we’ve found a compromise to satisfy Emily’s desire to go travel for a year, and my desire to continue to move forward with my career. We cannot wait for this coming Friday, March 27th, when we’ll say “Goodbye, for now.” to Austin, and embark on a new journey.