Grab Bag Weekend Trips

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I first heard of, what I’m going to dub “Grab-bag Weekend Trips” in the book Die Happy: 499 Things Every Guys Gotta Do While He Still Can, which I highly recommend any guy (and girl) who enjoys planning fun weekend stuff, like I do, to purchase.  You can get it here.

A grab bag weekend is something they suggest as a way to ensure staying in touch with your college friends.  I’m fortunate enough to see most of mine on a semi-regular basis.  I have a small group that’s also based in southeastern PA that I see rather frequently and the rest of us seem to always seek each other out if it’s been more than a few months, so I haven’t needed to implement something like this just yet.  That being said, it’s a really cool idea that I’d like to practice,  That being said, the control freak in me might really hate it.

How it works is that a group of you (I’d suggest no more than 4 or 5) pick out as many weekends in an allotted period of time (year?) and assign everyone a weekend.  Now, you’ll have to lay out these weekends in advance to ensure that everyone is free.

Each person is then tasked with coming up with a getaway for their weekend: destination, lodging, activities, itinerary, and reservations.  The fun part is that the rest of the group doesn’t know until a night or two before.  The benefits are that, aside from the weekend you plan, you get X many weekends a year that you know you’ll spend with people you like, won’t have to worry about planning, and hopefully will experience something new or something you might not necessarily ever try on your own.

The cons are that you could end up doing something godawful (like say, a yoga cleansing weekend) or completely ruin your budget when your buddy books you a round trip ticket to Vegas (I like Vegas just as much as the next degenerate, but it’s a place to be revered and feared…bank accounts and livers need time to work their way up to it’s particular brand of debauchery).  To prevent these snafus, set some ground rules.

  • Pick people you know won’t half ass it.  Make sure the friends involved will actually go out of their way to think of something fun and exciting and keep the rest of the group in mind.  This ensures great trips from everyone’s end.
  • Set a time limit and a budget.  Discuss the max spent on lodging and activities.  Don’t forget to factor in gas and spending money.  Also, will you be rendezvousing after work on Friday or will people be calling half days.  These are crucial details that need to be covered before anyone starts planning anything.
  • Decide when you’ll reveal the trips to your buddies.  In a perfect world you could surprise them on a Friday with something awesome, but in reality you should give your friends a heads up so they could pack accordingly.  You don’t want people showing up at the beach with no swim suits or walking into the lobby of a 4 star hotel with a 30 pack of Keylight (scratch that last one, you want your friends doing that sort of thing).
  • Don’t think that you have to go big.  Everyone wants to go to AC or Vegas of NYC. Everyone’s also been there before.  Try smaller, less traveled to cities like Baltimore or DC or Pittsburgh or Rochester, or scratch the city and do camping in NY or rafting in WV.
  • Make sure that you’re hotel is located within walking distance of some adult watering holes and do some preliminary research to see which ones seem fun.  Try to plan at least one big activity (skydiving, paintballing, rafting) and a few smaller ones (going to see the Rocky statue if in Philly, walking around the monuments in DC), so that if you have downtime you’re not bored.
  • When it’s your turn to plan, don’t wait till the last minute.  Also, do some rese arch.  Yelp and tripadvisor are your friends here.  Make sure you read reviews of everything you want to book.  You don’t have to take them at face value, but I’ve never not regretted looking up reviews.  I have regretted not doing so.
  • That being said, be flexible.  Run a tight ship but don’t be a Nazi with your itinerary (my friends are probably reading this and thinking something along the lines of “pot, meet kettle”).  That isn’t to see that your guests (if you’re the one in charge, technically they are your guests) can blow off what you have planned, but just leave some breathing room and room for surprises.  Ex: If you pay for skydiving, everyone is going skydiving, but if the bar crawl you have planned doesn’t pan out exactly how it’s supposed to, just roll with the punches.
  • Don’t blame the planner for things that go wrong.  Even the best planned trips hit snafus. Also, people might need to skimp in one area to go big in another.  So, if your hotel is in a less than desirable area of town, the ATV trip you reserve consists of driving around a farm and not the “wilderness” advertised, or you all get so hungover you have to cancel Sunday’s activities, don’t freak out.  The point of this is to spend a weekend with friends you didn’t see, and if you’ve already gotten everyone together, you’ve already won.

*If anyone does one of these, do me a favor and let me know how it goes.  I’m curious for stories.

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