After much research, post-its, deliberation and discussion, I've settled on a user experience for my mobile app. The name will likely change from Serendicity to something else, but that is yet to be determined.
I'm now approaching the experience like that of a video game. Players often have to get from point A to point B (or essentially, a final goal/destination). In order to give them a sense of agency, players are often allowed to explore freely as they go from point A to point B. Sometimes even side quests are thrown in. This made me think of how travelers often have a set of destinations (at least one) in mind that they'd like to visit.
What I want to create is an experience where travelers pick a destination (landmark, restaurant, neighborhood, museum, park, etc), and what the app will do is guide them there. However, it won't give them the fastest route - it will give them an alternate route that is full of "side quests" (what I will be referring to these alternate activities/stops for now), or other things they should see/do/experience along the way. Important variables here are current location, destination, time, and preferences.
Current location and destination are self-explanatory. This will determine the start and end point of the itinerary. Time is an important factor because travelers will have different amounts of time to spend on these itineraries. Ultimately, preferences are important because the itinerary should be personalized and curated. All the activities/stops will be rated in order to provide travelers with the best possible experience.