Visit Baltimore has introduced a conversational AI travel assistant named Chessie, a planning tool that sits in a corner of the website and fields questions about neighborhoods, dining, events, and full itineraries. Chessie runs on Matador Network’s GuideGeek platform and works on desktop or mobile without a login or app download.

Chessie is a legendary sea monster said to lurk in the Chesapeake Bay and the persona leans into the city’s friendliness. Travelers can throw it something broad like “What are the best attractions in Baltimore?” or something oddly specific, such as a four-day itinerary for a family of five with kids ages 4 to 9 and it adapts to whatever preferences it is given.

“Visitors now expect instant, personalized guidance,” said Visit Baltimore President and CEO Kireem Swinton in the announcement, framing the tool as a way to scale his team’s firsthand local expertise rather than replace it.

Baltimore joins a growing list of destinations that have plugged into GuideGeek, including New Zealand, Greece, and New York City. Matador points to its own consumer research suggesting travelers trust AI for trip planning more than for almost any other task — a signal that a branded assistant is shifting from novelty toward a genuine front door to the destination’s website.

Chessie captures first-party questions and intent data that a static site never surfaces, and it meets travelers inside the AI planning habit many have already formed. Whether a custom-branded assistant becomes table stakes or stays a point of differentiation is the open question the rest of the industry is now watching.