A Silly Mission: Creating More Memorable Travel Experiences

Last week I spoke in San Francisco about the value of having a mission weaving through our travels. On the road, as in life, possessing a plan, even a ridiculous one, is better than aimlessly following the crowds. The right mission will pull you out of the tourism funnel and into places where you will meet genuine locals and have unique experiences.
Here are a few missions I've pursued on and off the Road Less Traveled:

• Writing a never-published guidebook to the Baltic states. - Researching the content had me popping my head into every bar, restaurant, hotel, and attraction in Tallinn, Riga, and Vilnius.  Something I would not have done as a casual traveler.
• Buying and riding a tandem bicycle around different neighborhoods in Hanoi, picking up a variety of passengers along the way to mic them up and hear their story - This would be an awesome cross-country mission. You'll have to watch the episode to discover why I was wearing a Christopher Columbus getup.
• Shoe dating in Malaysia - I went on a series of casual dates in Kuala Lumpur based on a clever concept developed between a high end women's footwear store and a matchmaking service. The mission soon changed serious when one of the women informed me about native people in Sarawak being exploited by corrupt industry and politics.
• Shooting a short movie in Romania for 700$ (included casting, wardrobe, logistics, and salaries for make-up specialist and actors).

And here are some silly ideas for future trips:​

• Throw paper airplanes off the 5 highest peaks in your travel destination.  Jazz it up by first designing the planes with names of friends, sentiments, or worries you'd like to ​let fly.
• Instead of just going to Vegas to party, take the Old Mojave Road to Vegas..  then party.
• Find the best croissant in Paris, the best cappuccino in Rome,  or the best taco truck in Los Angeles.  Put an interesting spin on the mission by forbidding the use of the internet or apps in your search.  All direction and advice must come from locals.
• Buy a traditional outrigger boat in the Philippines and sail it to different islands.  My buddy accomplished this for about 3,000$.  Alternatively one could buy a boat or raft in several countries and navigate down a river.  Sell it when the journey is done.
• Look for a missing treasure or into an unsolved mystery.   In the Philippines I've looked into a case of mass demon possession and chased the Pinoy vampire.  We're about to take a shot at finding Lost Dutchman's Mine on an episode that will appear in season 4 of Road Less Traveled.  The chupacabra, El Dorado, and Arc of the Covenant may still be out there...

Have any other great travel mission ideas?  Have you experienced travel with a silly scheme as a backbone?  Please tell me about it in the comments.