Plan Recurring Vacations With Friends

For one week each Summer, my great grandma rented the same Newport Beach house for all our extended family to gather under one roof. Crying babies, drunk adults, religious disputes, sand everywhere, frequent injuries, potato salad, no parking -- it was pandemonium. Each day we somehow stuffed 80+ people in that 2-bedroom house. I miss those days.

That was long ago. Now I only attend ad-hoc (e.g. coffee) and/or obligatory (e.g. weddings) gatherings. I haven't seen my closest friends in years. I can't remember the last time I laughed/cried with them.

These were foreseen circumstances. My current lifestyle was composed of intentional choices: I got married, had a baby, then moved to a new city. I made decisions with tradeoffs, and my relationships inevitably change under such conditions. This is normal adulting stuff.

But conditions have changed again, and now I'm reaping the time/energy/money/trust dividends I've been sowing all these years. I'm so excited to reconnect with my friends.

Unfortunately, vacations require planning. As the self-appointed shit-disturber of my friend groups, I am responsible for such plans. To minimize planning and maximize pandemonium fun, I want to gather as many friends as possible together in the same spots each year.

The lazy/smart strategy is to coincide with established events. Here are some anchors that might work for me:

But my anchors are not your anchors. Your list should contain all your favorite events, people, places, and hobbies.

I'll obviously need to trim my list down a lot, but I thought it would be helpful to share some heuristics on how I choose events/places:

• I tend to abandon projects that require recurring work. If I want to see my friends regularly, I must prioritize convenience over cost/comfort/charm.
• My favorite anchors are charismatic friends with huge houses.
• I avoid giants like CES, but my friends are obligated to work at the event. You needn't attend an event to use it as an anchor; plan some meetups before/after the event.
• If my daughter attends scheduled programs (e.g. school), we might want to consolidate all family trips to school breaks, i.e. Summer, Spring break, Winter break. Even if she is homeschooled, she may want to visit friends who can only play during school breaks.
• 3-day weekends are double-edged swords. You and your friends skip work/school, but so does everybody else. The US becomes more expensive and crowded on those weekends.
• Camping is usually cheaper than hotel/AirBnB, but avoid major parks during busy seasons.

Don't overthink it. People like to do fun things together, again and again. Recurring experiences accrete into traditions. And with enough time, your traditions become their own anchors for future generations to inherit. Such things cannot be planned, nor can they happen without planning. Have fun.