I rented month-long Airbnb stays in 6 different cities before settling in San Diego. Doing a test run in each city made my decision easy.
- Sophie London is an associate creative director who is now based in San Diego.
- She tried living in six cities: Nashville, Austin, Chattanooga, Montreal, Toronto, and San Diego.
This as-told-to essay is based on a conversation with Sophie London, a 30-year-old associate creative director at Team Lewis from San Diego, California about her relocation. It's been edited for length and clarity.
Since the age of two, I've called Massachusetts home. I loved Boston. In a way, I took pride in my ability to say I was from Boston —it says you have some pretty thick skin.
By my late 20s, I felt like I was about to hit my stride; work was going well, I was moving into a brand-new apartment, I had a great network of friends around me. I consider myself to be a very positive person — outgoing, bubbly, energetic.
Decided to leave my hometown
But when COVID hit, all of that dissipated. I felt stuck, stagnant, and likely depressed. I promised myself that once the pandemic was over, I would experience life in its most limitless sense.
My apartment lease was ending. I was going to turn 30 next year, and I felt pulled to see more of the world than my familiar Boston had to offer. I knew the streets of the area inside out and wanted the challenge of figuring out new cities. I craved variety.
The checklist for each city
I decided to take a year to find another place outside of Boston where I could make a new home. At the time, my job allowed me to work remotely full-time, which made it possible to travel.
I ended up renting month-long stays in Airbnbs in Nashville, Austin, Chattanooga, Montreal, Toronto, and San Diego.
My general checklist of what I was looking for in a city included:
- Recommended by a friend/word of mouth
- Excellent food scene
- Great walkability factor/high public transit score
- Creative/arts-centric
The general cost of the trip ended up being equal to the amount I would pay in rent when I was living in Boston, and I did my best to stick to it. Some months were cheaper than others, but it averaged out.
I also saved a lot of money only buying one-way plane tickets.
What it was like to stay in Nashville and Austin
I stayed in Nashville in May because I'm also a singer/songwriter, and the idea of staying in a music-centric city was appealing.
I thought I would love Nashville, but it out it wasn't everything I imagined.
I didn't have a car and everything felt so far apart. A walk to a drugstore would take a minimum of 25 minutes, so I was on my feet a lot. The Broadway bar scene was overwhelming for a single girl to walk around. The bachelorette party buses woke me up at 8 a.m. on Thursdays.
I decided that it wasn't exactly where I wanted to stay long-term, but I did make some amazing friendships and saw some fabulous live music.
Austin in June was next, because I had family there as well and had only visited on vacation for a few long weekends.
Like Nashville, it was a music-focused city with world-class barbecue and the kind of energy I wanted to experience living in for a longer period of time.
After Nashville and Austin, I came back to Boston to stay at my mom's house for a couple days to swap out my clothes before leaving for London on a week-long work trip.
After London, I came back to my mom's house for a couple weeks to get my next moves together and re-pack.
My experience in Montreal
I stayed in Montreal and then Toronto from August through October.
I had never been to Montreal and it had an incredible food scene I wanted to experience. The idea of staying where there was a language barrier was interesting to me, and I'd heard from friends that it was beautiful.
Montreal was gorgeous, but the language barrier (many people there speak French) was tough. I felt lonely on some days, and I don't think I could manage those winters.
Montreal has an amazing public transit system, though. I always felt safe and got around quickly without a car.
What it was like living in Toronto
I made an impulse decision to go to Toronto next, and it ended up being one of my favorite stops.
I spent each morning walking down Queen Street to get coffee and attend cycling classes. The public transit system was fast and reliable. I got to see the excitement of the Toronto International Film Festival (TIFF), and even got a Taylor Swift sighting.
I also ended up meeting a new love interest. It was as fleeting as it was exciting, but nonetheless worth it to experience romance in another country and far from my comfort zone.
I left Toronto the day before my passport expired and returned to Boston for the last half of October.
What Chattanooga was like
I'd made a friend in Nashville who had a condo in Chattanooga and invited me to stay that November at a ridiculous rate compared to Boston.
I ate well, joined a local spin gym, walked miles around their town center, drank lots of Tennessee whiskey, and played more trivia and BINGO than I ever have in my entire life.
I regularly visited NoogaNightlife.com — the city truly cared more about keeping its residents busy than any other city I'd lived in. Every night there were activities planned at various bars and restaurants, and they were widely attended.
Then for the first half of December, I went back to Boston. For the second half and the holidays, I traveled to Nicaragua with my previously mentioned Toronto love interest.
What it was like in San Diego
My employer was hosting a company-wide event in San Diego, our US headquarters, the first week of January 2023.
I planned to stay in San Diego after the event for my next Airbnb jaunt from January 9 to mid-February. I was always curious about San Diego and had heard that many Bostonians end up moving there and loving it.
Plus, my coworkers raved about it. Who wouldn't want to live five minutes from the beach and watch sunsets every night?
I ended up enjoying San Diego so much that I extended my Airbnb to March 15. The weather and plants made every morning feel like I was on vacation. I also made a point to try as many new restaurants as I could.
My coworkers became close friends. They wanted to show me everything San Diego had to offer. Sunset dinners and walking around Balboa Park became regular things.
When my work noticed how happy I was, they offered a relocation. I couldn't pass up the opportunity to stay.
My trial runs taught me a lot
I was glad that staying in these six cities made this a year of being uncomfortable in the best way possible for a few reasons:
- Embracing the culture: I tried out each place's culture, even if it meant attending an event alone. I had no one else to check in with. If I wasn't having fun, I left; if I was enjoying it, I stayed.
- Planning last minute: When people asked me, "What's next?" I'd feel a pang of anxiety, but it was exciting because I knew I'd figure it out — I just didn't know when. Things were planned super last minute.
- Living simply: I had to fit everything I needed in one suitcase, which was tough. But living with a capsule wardrobe forced me to select items that would get worn over and over and could match with everything. I ended up wearing a lot of black. Knowing it could all fit in a suitcase was satisfying.
- Starting over in each kitchen: Without my supplies and spices, cooking in an Airbnb wasn't easy. But that also meant that I got to dine out more at these cities' finest establishments.
In the end, my decision was easy. Being able to do a test run of each locale gave me the confidence to decide if it was right for me.
Discovering all the places that weren't the best fit for me helped me recognize when I was in a place that did fit.