BALTIMORE, July 7, 2026 /PRNewswire/ — Baltimore visitors have a new navigational tool to chart their course through Charm City. Visit Baltimore has launched “Chessie,” an AI travel assistant powered by Matador Network’s industry-leading GuideGeek AI platform, designed to help travelers easily explore everything the city has to offer.
Chessie is named after a bit of Baltimore folklore, a legendary sea monster said to lurk in the waters of the Chesapeake Bay. With an engaging persona that exemplifies the city’s friendliness, the new AI is available via an icon in the bottom-right corner of baltimore.org. Chessie is ready to plan full itineraries or provide information about neighborhoods, culture, dining, events, only-in-Baltimore experiences and more.
Visit Baltimore is meeting the rising expectations of visitors who increasingly rely on AI to shape their vacations. Chessie provides personalized responses and adapts to visitor preferences on desktop or mobile, all without requiring travelers to login or download an app.
“Visitors now expect instant, personalized guidance. Chessie provides that while showcasing the depth and character of everything our city has to offer, optimizing our team’s authentic, firsthand expertise,” said Visit Baltimore President & CEO Kireem Swinton. “We want Baltimore to be a city that’s easy to discover and impossible to forget, and giving visitors a smart, friendly tool to plan their journey is one more way we’re investing in that experience.”
Baltimore joins other destinations that have launched GuideGeek-powered AI assistants, including New Zealand, Greece and New York City. Consumers trust AI for travel planning more than any other task and Chessie brings unique Baltimore flair to that experience, building personalized travel plans and making it easier than ever to discover an exceptional destination.
Travelers can ask Chessie highly specific or vague questions such as, “What are the best attractions in Baltimore?” or “We’re a family of 5 with kids ages 4-9 traveling across the East Coast this summer. Can you please plan us a 4-day itinerary in Baltimore?”
Baltimore highlights travelers may want to discuss with Chessie:
- Historic sites, like Fort McHenry, the USS Constellation, and the Washington Monument
- World-class attractions like the National Aquarium, B&O Railroad Museum, and Baltimore Museum of Industry
- Must-see art exhibits at the Baltimore Museum of Art, American Visionary Art Museum, and The Walters Art Museum
- Cultural centers, like the Reginald F. Lewis Museum, National Great Blacks in Wax Museum, and the Frederick Douglass-Isaac Myers Maritime Park Museum
- Restaurants that serve up the best local cuisine, including crab cakes
- A seven-mile waterfront promenade passing through multiple neighborhoods
- More than 250 distinct neighborhoods, such as historic Fell’s Point, eclectic Hampden, and charming Mount Vernon
- Events happening year round throughout the city
“Travelers are increasingly turning to AI as their first stop when planning a trip, and destinations that embrace this shift are the ones that will win visitors,” says Matador Network CEO Ross Borden. “Chessie gives anyone curious about Baltimore an instant, personalized way to explore everything the city has to offer, from its iconic landmarks to its eclectic neighborhoods.”
About Visit Baltimore
Visit Baltimore is the official sales and marketing arm for the City of Baltimore. The 501(c)(6) nonprofit organization generates economic benefits for Baltimore and its residents through the attraction of convention, group and leisure visitors. In 2025, 28.7 million people visited Baltimore for overnight and day trips, generating $4.3 billion for the city’s economy. For more information, please visit baltimore.org.
About Matador Network
Matador Network is the world’s No. 1 media brand for modern adventurers and the creator of GuideGeek, the award-winning AI travel genius. With more than 15 million followers across social media, Matador became a leading travel brand through its production of feature articles, city guides, creator-first content and original streaming shows. Matador’s videos generate over 140M monthly views and its content distribution deals with major airlines, airports, gas stations and ride sharing companies reach travelers throughout their journey. The GuideGeek AI platform has over 1M consumer users and powers custom conversational AI for dozens of travel brands and destinations. matadornetwork.com | guidegeek.com
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SOURCE Matador Network
