Steves started his career by teaching travel classes at his alma mater, University of Washington, and working as a tour guide in the summer. At the time, he also worked as a piano teacher (his father had owned a piano store). In 1979, based on his travel classes, he wrote the first edition of Europe Through the Back Door or ETBD, a general guide on how to travel in Europe. Steves self-published the first edition of his travel skills book ETBD in 1980. Unlike most guidebook entrepreneurs, he opened a storefront business, which at first was both travel center and piano teaching studio. He held travel classes and slide shows, did travel consulting, organized a few group tours per year, and updated his books. He did not provide ticket booking or other standard travel agency services. He incorporated his business as "Rick Steves' Europe Through the Back Door". The store was in Steves' hometown of Edmonds, Washington (a city north of Seattle). The company's headquarters are still in Edmonds.

During the 1980s, his business grew slowly but steadily. He brought out more guidebooks, published by the alternative publisher John Muir Press, under the label "2 to 22 Days in...." His group tours competed more on sincerity, small group size, and service than on price. He sold railpasses and travel gear in his store and eventually by mail order, ran a trip consulting service, and held slideshows and lectures. Gene Openshaw, a childhood friend of Steves', wrote most of the history and art material in his books. Dave Hoerlein, an architect by training, drew maps for the guidebooks and became a popular tour guide.

In 1991, the company had approximately five employees. That year, Steves began producing TV shows about European destinations. These shows were produced with his own funding and given to public television stations for free. The TV shows made him a nationwide figure, and his tour, guidebook, and merchandise businesses boomed. An important factor in the company's success was the information exchange possible between the various parts of the business. The tour business benefited from the yearly guidebook updating and his trip consulting businesses, and vice versa. The company is privately held by Steves.

Steves advocates independent travel. His books and media deal with travel mainly in Europe, and are directed at an American audience. As host, writer, and producer of the popular and long running Oregon Public Broadcasting television series Rick Steves' Europe, and through his travel book, he encourages Americans to become what he calls "temporary locals." He encourages his readers and viewers to discover not only major cities, but also cozy villages away from popular tourist routes. Steves' television series, guidebooks, radio shows, mobile applications, and his company's European escorted bus tours attract fans known as "Rickniks".

Steves' relationship with public television began with his first series, Travels in Europe with Rick Steves, in 1991. Since then, he has become one of public television's top pledge drive hosts, raising millions of dollars annually for stations across the U.S. He writes and co-produces his television programs through his own production company, Back Door Productions.

Since self-publishing his first book in 1980, Steves has written country guidebooks, city and regional guides, phrase books, and co-authored Europe 101: History and Art for Travelers. His guidebook to Italy is the bestselling international guidebook in the U.S. In 1999, he started writing in a new genre of travel writing with his anecdotal Postcards from Europe, recounting his favorite moments from his many years of travel. Steves' books are published by Avalon Travel Publishing, a member of the Perseus Books Group. In 2009, Steves published the book Travel as a Political Act, a guide on traveling more thoughtfully.

In addition to his guidebooks and television shows, Steves has expanded into radio, newspaper and mobile applications. In 2005, Steves launched a weekly public radio program, Travel with Rick Steves. Focusing on world travel, each program has a guest travel expert for interviews, followed by call-ins with questions and comments. In 2006, Steves became a syndicated newspaper columnist with his Tribune Media Services column, and in 2009, mobile application versions of six of Steves' European tours launched for the iPhone.

Steves ‘support[s] the decriminalization of marijuana among responsible adult users in the USA’. According to Steves:

"Like most of Europe, I believe marijuana is a soft drug (like alcohol and tobacco), not a hard drug. Like alcohol and tobacco, there is no reason why it shouldn't be taxed and regulated. Crime should only enter the equation if it is abused to the point where innocent people are harmed."

Steves is currently on the Advisory Board of the National Organization for the Reform of Marijuana Laws. Steves hosted an ACLU-sponsored educational program broadcast, Marijuana: It's Time for a Conversation.

Steves married, and he and his wife Anne had a son and daughter, Andy and Jackie. When their children were young, he still traveled overseas with them and produced segments in his books with advice as to how to successfully manage a European trip with children. The couple divorced in March 2010.

In 2005 Steves and his former wife purchased a 24-unit apartment complex in Lynnwood, Washington and had it fixed up to serve as transitional housing for homeless mothers and their children. Steves is allowing free use of the complex for 15 years – leaving management responsibilities to the local YWCA Pathways for Women, while Rotarian in the Edmonds Noontime Rotary Club help maintain the buildings, do grounds upkeep, and provide everything from the furniture to the flowers. In addition, the club raised USD $30,000 in donations to build a play structure for the children of Trinity Place. About 100 mothers are expected to ultimately live there.

Steves is an active Lutheran, and has written and hosted educational videos on subjects such as Martin Luther and the European Reformation of the Church. He also raises funds for the charity Bread for the World.Steves spends about a third of every year in Europe, researching guidebooks, filming TV shows, and making new discoveries for travelers. He lives and works in his hometown of Edmonds, Washington, where his office window overlooks his old junior high school.