How to take the best vacation possible

I like Kevin Kelly’s two modes of vacations:

• Retreat: Travel to escape the routines of work, to recharge, relax, reinvigorate, and replenish. In this mode you travel to remove yourself from your routines, or to get the pampering and attention you don’t ordinarily get, and ideally to do fun things instead of work things. So you travel to where it is easy.
• Engage: The other mode is engagement and experience. In this mode you travel to discover new things, to have new experiences, to lean into an adventure whose outcome is not certain, to meet otherness. You move to find yourself by encountering pleasures and challenges you don’t encounter at home. This kind of travel is a type of learning.

Of the two modes, I heavily favor the latter, and so I wrote this wonderful list of key criteria for optimizing your vacation.

Overall goal: Be present and do whatever you can to limit any distractions, which means having just enough sensory overload and fulfilling the criteria below.

Key Criteria:

• Learn something new
• Own your own schedule
• Meet new people
• Have a new/novel experience
• Eat well
• Be moving and feel good/healthy
• Let loose BUT not enough to lose control/time
• Be outside

Tips (many borrowed from Kevin Kelly):

• Set your trip up with a great, self-selecting population already, whether that’s traveling with a group of affable mutual friends or a group trip based around a passion
• Take first class ground transport (trains, buses) in intra-country travel to meet people: you’ll find most interesting people who won’t be there to ask something from you.
• Look up the Lonely Planet Kids guide: it’s actually fun stuff and not just food, bars, and walking to landmarks
• Stay overnight at a Korean sauna for both accommodation, relaxation and experience (like Wi Spa in LA or SpaWorld in Osaka)
• Organize your travel around passions instead of destinations: An itinerary based on obscure cheeses, naval history, dinosaur digs, or jazz joints will lead to far more adventures and memorable experiences than a grand tour of famous places. It doesn't even have to be your passion! It could be a friend's, a family member's, or even one you've read about.
• If you hire a driver or use a taxi, offer to pay them to take you to visit their mother. They'll usually jump at the chance. They fulfill their filial duty, and you get easy entry into a local's home with a high chance of tasting home cooking. Mother, driver, and you all leave happy.
• The most important factor when selecting travel companions: do they complain or not, even when complaints are justified? No complaining! Complaints are only for post-travel debriefing.
• In new countries, live authentically: learn the major industry/export and try to experience it in-person, visit the local gym, go to the local grocery story, and my favorite: visit a cemetery