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I've traveled and worked remotely in 50 U.S. cities: Here are the top 4—and they aren't New York or LA

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Kimanzi Constable is a full-time digital nomad who has lived and worked in three continents. One of his favorite places to work remotely is San Juan, Puerto Rico, where he spent his weekends surrounded by nature.
Photo: Kimanzi Constable

In September 2021, my wife and I sold our house, car and possessions to become full-time digital nomads.

But even before the pandemic made remote work a popular trend, I've lived and worked remotely in more than 50 U.S. cities.

We run both of our businesses — a consulting firm and education program — online. Combined, they bring in $19,000 a month in revenue. High-speed internet is a must wherever we go. We also value places that have gyms, grocery stores and entertainment within walking distance.

I've always loved big cities: I spent six months in New York City and three months in Los Angeles. But there are so many less crowded and less expensive options for a working vacation.

Here are some of my favorite (and what I think are the most underrated) cities:

1. San Juan, Puerto Rico

Average weekly cost for one traveler: $1,219
*Source: Budget Your Trip, which compiles numbers from real travelers

If you live on the East Coast, Puerto Rico is only a few hours away from most major airports.

San Juan gives you city vibes while being on an island. The city center is walkable, with much of what you need within 30 minutes. And the Autoridad Metropolitana de Autobuses bus system charges just $0.75 per ride.

Kimanzi Constable and his wife explored Puerto Rico's El Yunque National Rainforest while they worked remotely in San Juan.
Photo: Kimanzi Constable

Some excellent coworking areas exist in Old San Juan and the city center. One space we used was Cocohaus, which offers a day pass for $20, or a five-day pass for $90. Access comes with fast WiFi and free coffee.

The food in San Juan is delicious and affordable, and the grocery stores carry many familiar brands that you'd find in the U.S.

There's also plenty to do after you log off, like visit the Luquillo Kiosks, take an ATV ride in the El Yunque rainforest, walk along Old San Juan or explore the city's nightlife options.  

2. Milwaukee, Wisconsin 

Average weekly cost for one traveler: $985

Milwaukee, where I was born and raised, offers work and hotel options at an attractive price. It's also just a 90-minute drive to Chicago, making it the perfect starting point for a larger trip. 

The city center is set on the coast of Lake Michigan, and the downtown area is bustling with coffee shops and coworking spaces.

Downtown Milwaukee is situated on Lake Michigan and offers a variety of shopping and restaurants.
Photo: Kimanzi Constable

One place I often go to is the Iron Horse Hotel, which has a beautiful lobby and library to work in. Another favorite is the Wantable Cafe.

The Jazz Estate has live music and theme nights, and The Brownstone is a Black-owned social lounge with DJ sets. I recommend Kopp's Frozen Custard for sweets, and Lakefront Brewery for its famous craft beer.

3. Atlanta, Georgia 

Average weekly cost for one traveler: $954

Our daughter attends college at Georgia Tech, so we visit Atlanta often.

In Midtown, there are excellent coffee shops and restaurants within walking distance, and plenty of Airbnbs in high-rise buildings that offer amenities like fast internet, gyms and office space.

The rest of the city is easily explorable using Atlanta's public MARTA transportation system.

A stroll along Atlanta's BeltLine, a network of trails and public spaces that surround the neighborhoods in the city's center, brings a new understanding of African American culture.

Atlanta's BeltLine has 22 miles of trails that connect many of the city's neighborhoods.
Photo: Kimanzi Constable

Atlanta is also home to the National Center for Civil and Human Rights, Martin Luther King, Jr. National Historical Park, Ebenezer Baptist Church and multiple historically black colleges, all of which are worth a visit.

You'll find amazing southern food in every corner of the city. A few of my favorites are Soul VegetarianPaschal's, Atlanta Breakfast Club and the famous Mary Mac's Tea Room.

4. Sarasota, Florida 

Average weekly cost for one traveler: $1,954

My wife and I spent three years in the Sarasota-Bradenton area. Voted as one of the best cities to live for multiple years in a row, it's a great place to travel and work.

Sarasota feels like a small town with many friendly coworking areas and coffee shops. Some of our favorites are BOLD Cowork Sarasota, which offers day passes for $25 or monthly passes for $50, and Lab SRQ, which offers a $30 day pass that includes coffee and snacks.

If you prefer to work from a café, I recommend checking out Breaking Wave Coffee

Kimanzi Constable and his wife like to work from local coffee shops like Breaking Wave coffee when they visit Sarasota — but sometimes they just go to Starbucks!
Photo: Kimanzi Constable

When the workday is over, you're surrounded by white sand beaches on the Gulf side of Florida, most of them are just a short drive from town.

Plus, there's no shortage of fresh seafood. While somewhat pricey, the local restaurants are worth the splurge. I recommend Dolce ItaliaDuval's Fresh Local Seafood and Café L'Europe

Kimanzi Constable is an entrepreneur and a freelance writer. His work has been published in Fortune, Entrepreneur, Black Enterprise, NBC, Travel & Leisure, CBS and Parents. Follow him and his wife on YouTube to keep up with their travels.

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