Wednesday, July 16, 2014

How to Plan an Effective ‘Guys Road Trip’

I have done a lot of trip-planning in my day for all sorts of adventures, but none of them more frequently than buddies road trips. There is just something about hitting the open road with anywhere from a couple to a dozen of your good friends that can almost guarantee a great time! 
My exquisite planning has seen us through successful automobile journeys to great cities like Pittsburgh, Columbus, Nashville, Montreal and Philadelphia. While I’m not saying that any of these trips were without their road bumps (pun intended), they all stayed on track thanks to careful research and focused execution. 
The challenge with being the group’s “planner” is that you are faced with the responsibility and pressure of planning something that meets or exceeds your friends’ expectations. The plus to this is that you have full control over all of the details like dates, budget & itinerary. While this role isn’t for everyone, it can be quite rewarding if you go into it prepared. Here are some of my best tips: 
Note – these tips are based around a 2 to 4 night, single-destination trip where travel is done by car/van. 

Good old open interstate

1)      Set Trip and Payment Dates
Everyone will say they are “interested” in a trip without a set time-frame for both the trip itself and payment. Plan ahead and pick a date that works for you, then give a reasonable deadline for your party to provide the cash. Don’t get caught waiting for stragglers and be firm with your deadline. Book hotel room(s) and car rental (if needed) for only the people who have committed with cold hard cash. If you’re a nice guy you can assist any late-comers with booking their own accommodations themselves (or in another small group). 
2)      Over-charge, don’t Under-charge 
Ensure you collect enough money from everyone to cover the full hotel, car rental (if necessary) and gas costs. When doing your math, err on the side of caution and inflate the price slightly. Keep in mind there are things like road tolls, hotel parking, in-room phone use or other small charges that may arise during the trip. By collecting a little extra at the start, you don’t have to nickel and dime your friends at every turn.   
3)      Know Your Group and Plan Accordingly
Is the bulk of your travel party big spenders who like to live large and have cash to burn? If so, by all means go all-out. But if you party is like mine and wants to cram the most fun into the tightest of budget, keep that in mind while planning. You can force them to spend a little out of their comfort zone to ensure you secure quality accommodations (see #4 below), but don’t force them to break the bank just because you want to. Secondly, if you are travelling with married guys they will likely have different tastes and expectations than those of the 'single and looking' demographic. The focus on day-time sight-seeing vs. nightlife should be weighted based on the group. 
4)      Get a Hotel that Works 
The Four Seasons is not required, but find a hotel that will suit your needs. Use TripAdvisor and find something that is a fair price but still decently reviewed. Four grown men in a tiny room doesn’t work (I’ve tried it). Try keeping it to three per room maximum. It is a known fact that hotels away from the downtown core are cheaper than those in it, however do some research and look at all of the factors. Is a $20 cab ride or time consuming public transit to the heart of the city worth saving a few bucks on hotel costs? Note: This is a guy’s trip (see: boozing), the vehicle that brought you into the city won’t be (and with some exceptions, shouldn’t be) moved until you are heading home. 
5)      Enjoy The Journey as much as the Destination 
My typical road trips are anywhere from 2 to 4 nights long. A rule of thumb I like to go by is no more than 4 hours of driving per night spent away. Any longer and the time on the road just simply won’t be worth it. Since these trips are short, it’s best to make the journey as much a part of the fun as the destination. For us this begins with ‘Duty Free’ shopping when crossing the border. Nothing gets our group more psyched for the trip than a rock bottom price for 24 cans of Coors Light or a 40oz bottle of Crown Royal. In addition to this it’s fun to keep an eye out for interesting road-side restaurants and of course have some crowd-pleasing music on hand. 
6)      Set Rules and Expectations 
Not to be everyone’s ‘Dad’, but as the planner of the trip you and your credit card are responsible for any negligence on your group’s part.  Ensure they know and respect the 'No Smoking' rule in the hotel room and rental car. If you have a group that might get a little rowdy, let them know that it is a quality hotel, not a house party and you don’t want to be kicked out or charged for damages. If you’ve chosen your group wisely they will respect your planning and happily oblige. If there is a 9am wake-up call to hit the road, make it clear that you don’t want to be waiting around for certain people because they chose to party a little too hard on the last night. 
7)      Have a Food Plan 
Nothing kills the vibe of a vacation more than everyone sitting around in a hotel room for an hour trying to figure out where to eat. Have a list of some interesting restaurants at the ready. It’s a guy’s trip so leave fine (or even semi-fine) dining out of it. Focus on famous local cuisine like cheesesteak in Philly, poutine in Montreal or Pizza in NYC. Research good street food and late-night eats as road-trips are usually short and busy so you’ll often look to grab something on the go. 
8)      Set Meeting Places 
If you are a Canadian travelling in the US or vice-versa chances are you will not be able to readily call or text your buddies if you split-up. Have a set time and place to meet up for dinner or night plans. Don’t feel like you have to always “keep the group together”, remember this isn’t just your trip, and everyone wants to get something a little different out of it.   

Have any of your own tips or questions about road trip planning? I would love to hear from you in the comments! 
Mike @ Palms & Pints 


  1. The plan is really effective! I love Guys Road Trip! In fact, i would like to take a sound trip in vin rejser moldova.

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