Consider a newly minted Private Pilot in the San Francisco Bay Area, where I'm based. A beautiful and memorable ride for family and friends is to be flown along the 101 highway, over San Francisco's landmarks, Golden Gate Bridge and perhaps a lunch or dinner stop at Half Moon Bay airport. This flight is ideal with a transition through San Francisco's Class B airspace. Student pilots aren't allowed to fly through solo. However, a flight with my instructor during my student pilot days gave me the confidence to make the Bay Tour with friends right after I earned my license.
What fun flight do you need help to get comfortable with?