Planning a Solid Group Weekend Trip

I legitimately enjoy planning vacations and weekend trips (which is partially how this blog got started). I like researching different places to go and things to do. I enjoy putting together hypothetical itineraries and bothering my friends with over-wordy Facebook messages describing said hypothetical itineraries. I like being in charge and like organizing things (some might use the words control freak); every group of friends needs this person and I’m more than happy to be one of those taking the reigns.

I’ve learned a couple of things over the years that I usually do/take into account during various stages of trip planning and have deemed myself generous enough to share this knowledge with you.

It’s worth noting that I’m talking about planning group getaways for friends. I usually plan for an average of 5-10 people, usually comprised of college friends, high school friends and family members  looking to let off some steam for the weekend. 9 out of 10 times, the locations is secondary to the company. This type of  getaway is not the time to have an fully immersed cultural experience or completely conquer a new locale. Leave those outings to smaller groups of people that you don’t necessarily need to catch up with.

Also, my friends also drink like fish, which this list will reflect. I’m all up for being able to have fun without alcohol, but when having these mini-reunions, that’s usually just not the case.

Here goes:

1) Bring everything you need with you (and make it clear that everyone else should)-

Listen, I realize that sometimes just trying to make it out on the road at a reasonable hour after work is a feat in itself and that sometimes you don’t have time to do all the running around you had planned. That’s why don’t wait till the last minute when it comes to weekend travel. If you’re going to be busy then pack Thursday. Make a list of what you need. It’s not overkill, it’s smart.

Contrary to popular belief, there is not always a nearest grocery store, Wal-Mart or CVS. Unless you research ahead an find that there is one within a few blocks, pack everything you need before hand and don’t plan on getting supplies on site. No one else wants to waste a half hour waiting for you to find shampoo or even worse, a new outfit (at the risk of generalizing this goes to the female members of your party. Keep the peace and pack ahead. This goes double for booze. States have very different alcohol laws, so don’t assume you could pick up a 6 pack at Wawa (all you none-PA residents) or that bars offer take out (which I recently learned is a very Pennsylvanian thing).

2) Don’t  go (too) crazy Friday night-

You’re on a weekend trip. You’re not on a one night bender. Control yourself to the best of your ability Friday night. You most likely will be hungover on Saturday but you don’t want to have one of those epic ones that prevents you, and by proxy then, the group from having a good time. If you have something planned for Sunday, don’t get too out of control Saturday night. If Sunday is only driving home, then by all means go all Hangover style-but be aware of check out times (this goes double if you’re renting a house).

Banish the person who brings the handle of Fireball. Make them sleep in the hall.

3) Pick your place of lodging in accordance to what you’ll  be doing-

A lot of times cheaper hotels are on the outskirts of town. If you’re getting up and traveling the next day, this might be a bonus and save a lot of unnecessary traffic time. If you are looking to barhop and will have to call two cabs to come get you, then this might be a pain in the ass. Also, if you’re traveling in Pennsylvania, the only city with reliable cab service is Philly. Plan accordingly.

4) Location, Location, Location-

I’m not talking about lodging here. I’m talking about where you’ll be going on the trip. Where is everyone coming from? What’s a centralish location (or at least a comparable drive for everyone)? Where can people easily carpool together? Unless you decided ahead of time that everyone can take a day off on Friday, where can everyone feasibly arrive at a decent time? Make it reasonable and equal for the most part.

*Sidenote: Be aware of everyone’s ETA (Estimated Time of Arrival).

5) Plan an athletic activity-

Most (most being the key word here) successful group trips I’ve been on involved some sort of athletic activity, usually completed early Saturday afternoon. It gets you out doing something fun (and sometimes new), it ensures you don’t wallow in bed all day, and plus, I generally enjoy being active. It will also help you feel better after your Friday night debauchery. In the past I’ve done trips where we’ve rafted, gone kayaking, played paintball, ATVed, ziplined, ran a race, rock climbed, snowshoed, etc.

Now, if your trip is for say, a concert, or St. Patrick’s day, feel free to keep Saturday free for day drinking (or if it’s a beer-centric friend’s weekend).

6) Plan two others activities, one that can be discarded-

It’s a good thing to have several activities planned just in case. I always book one in advance (usually the athletic endeavor), that way no one can change the course of the trip at the last minute, but it’s good to keep some on standby in case you have some downtime. Keep these cheap and easy: a hike, aquarium visit, beer tasting at a local brewery, and make sure they aren’t something everyone needs to do.

On a recent trip to Baltimore for a Zombie Mud Run we went to the aquarium on Sunday. It was something to help us detox, ease out of the weekend and made us feel like there was more to us than being raging alcs.

7) Make sure everyone is on the same page before the trip-

This just comes down to communication. Does everyone plan on going out Friday or would some rather stay in so they’re primed for whatever Saturday brings. Are you traveling with people who like going out to eat nice places or is Subway fine? Getting this information from the get-go ensures no arguments or passive aggressiveness (mostly).

Sidenote: I highly recommend starting a Facebook message about the trip. You could do email or text, but I prefer the FB chat as everyone can chime in immediately, you can include links AND the content is easily accessible.

8) Scout out your location-

This is taking number 4) and expanding on it. Where are the nearest bars? Where are the ones that look fun? What’s the public transportation like in the city? What are the different neighborhoods like?

I always like to have at least an overview of fun places to go and the geographical makeup of a locale before I go. Playing it by ear could absolutely be fun but have at least an idea of where you should be (as well as where you shouldn’t) be going.

9) Be flexible

This one is admittedly hard for me. I’m that guy who makes a schedule and likes to adhere to that (and who everyone else bitches about when they’re in the shower). I’m usually the first one up and the one then cajoling everyone else to get out of bed. I want to be certain places at certain times and in a sense it’s necessary to have someone anal retentive in your group (my friends are rolling their eyes and saying, “no, it’s not”). That being said, learn to roll with the punches. If your perfect itinerary is blown, so be it. Remember, you’re here first and foremost for the company and if everyone is having a good time, don’t be the Debbie Downer.

10) Pack snacks and Gatorade-

You will wake up later than you want. You may not have time for breakfast. The person who brought cliff bars and doughnuts is a savior. See also: you return home circa 2:30 AM and need Gatorade and a slim jim. Have them in your room. As previously mentioned, Wawa might not be right across the street (and if it is, well then you my friend hit the jackpot).

12) Don’t rely solely on GPS-

GPS’s are fine 99% of the time. Sometimes they don’t work. Also, there are rural parts of PA and NY (probably  other places too-I’m just speaking from personal experience) where you won’t have service. Printing out mapquest before hand and at least having a general idea of where your route should be taking you can save a lot of headaches.

13) Keep everyone’s budget in mind-

You’re the one planning the trip right? That means you decide what you’ll be doing and where you’ll be saying, correct? Wrong. If you’re around my age then you’re at that weird stage of life where some people are making close to 6 figures while others are still in grad school scraping by on a bartender’s salary. Pick hotels and activities and places to eat that aren’t going to bankrupt any of your friends. It’s best if everyone is having fun, not just you.

14) Find co-conspirators-

It’ll be easier if you have a friend or two willing to help with the planning and execution process (I’m lucky in this regard). At the very least find a few people willing to help put down deposits.

15) Lie Your Face Off-

Telling everyone you need to be at your rafting reservations at 10 will ensure that you are all there for the 11:30 sign in.

*Bonus: don’t invite cheap friends.  Thankfully most of my friends have little concept of the value of money, so I’ve yet to encounter this problem, but you will be splitting a lot of things: cabs, tips, bills, etc, and you want to make sure everyone is ponying up the correct amount.

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