Finding new things to do and places to visit while traveling isn't easy. Even when people try hard to plan, they can be caught off guard by the weather. To solve this, we turned IBM's Watson into a smart travel guide. Unlike other options, Watson could gather all the weather information, city events, and their locations, and combine these details to give travelers the best recommendations. To promote this service, we used flight arrival times at major destinations and, based on when people landed, provided suggestions for events happening in the city shortly after their arrival accordingly to the weather.