Logistical lessons from a fraternity travel planner

Sometimes, if you want to guarantee that something is done right, you need to do it yourself.

This was my thought process with a lot of things, especially those involving my time and my money. This often coalesced in the form of spring break trips (and similar excursions). I knew I wanted to bring a fun experience to the table and showcase my logistical skills. One thing I did know about my fraternity that created the challenge for me was their apprehension to spending money and their lack of time management. Fun!

This post is about travel planning and I’ll mostly focus on my spring break trips, of which there have been three (avg. attendance of 12). However, I’ve applied some or all of the same methods to houseboats, camping, road trips, etc.

Phase 1: Initial survey and location research

You want to take a trip with the fellas, that’s great! The most difficult part of all this is finding dates that work for everyone. With spring break, it’s no issue since almost everyone is in school and can get work off. Outside of that, however, you will be hard-pressed to find a time that works for everyone. That’s life. A recent example would be our 2023 houseboats weekend trip. That brings me to my main point.

Sending out a survey (think Google Forms) is a good first step in making this happen. In the case of that houseboats trip, I included a question for every single weekend this summer, notating important ones (Father’s day, weekend before the 4th, etc). They could answer with yes, no, or maybe/depends. Take those results, see which ones have the highest number of “yes” responses, there’s your dates for the trip. Sometimes you’ll need to defer to the 2nd highest response. It showcases how an idea (”Let’s rent a houseboat!”) with, say, 19 people indicating they would want to participate, can turn into 10 committed members once you involve a date and time.

What else should you include on the survey? In the case of spring break, a selection of potential destinations. This can be simple or complex, depending on the time and effort you want to put in. In my case, before I’ve even crafted a survey, I’ve come up with my own destinations and researched 5-10 AirBnbs in the area. Part of the fun of trip planning is choosing the accommodations–you get the final say in where the group is going to stay. With that information, you can deliver an average price alongside each destination in the survey. Be careful with this, as it can influence people’s decisions away from a good destination if the price is too high, when the price can also depend on other factors such as the length of the trip and number of people in attendance. Make sure to include a picture of the location that gives a good idea of the area. Generally, city skylines or overhead shots of the location are sufficient.

From the spreadsheet, you can get an idea of the information I was after: price for the week, max occupants, and buy-in per person. Transportation factors in as well, but I didn’t include that in the listed price because people could fly for convenience or choose to drive/carpool if they wanted to save money.

Once you’ve populated your survey with some regions or cities that people might want to go, you’ll want to collect some sentiments about the trip. People vary in how they vacation and why they go. While it is spring break, and the fun of that is on everyone’s minds, it can be difficult to maintain a 7-day bender. I realize I am putting some survey elements out of order, as upon reviewing my 2022 survey, I gathered sentiments first. Depending on your group, you may want to gather responses on the following topics:

• Over/under 21 (can someone go to the bars)
• Max amount they’d be willing to spend on lodging, not including food or travel
• Max amount they’d be willing to spend on travel expenses (gas/flights)
  • Are flights even an option for them?
• Goal of the trip (relax, party, explore, all, etc)

While I was reviewing the survey to gather these sentiments, I also realized I sent out two surveys. The first one did NOT include prices for each of the regions presented. The second one did, after gauging the interest for the first set of locations.

Phase 2: Commitments and money

Now, with 10-20 responses, you have a good idea of what the group wants and can cater your planning time towards that. Don’t be afraid to make command decisions about certain aspects of the trip if you think it is best for the group. Most importantly, stay transparent and involved during this part of the trip planning process.

There is a catch-22 situation here in that you cannot book an Airbnb without a good idea of your group size, but you cannot provide an accurate price to the group without knowing how many people are coming. Most people do not want to pony up a deposit (generally set at 20% of the total cost: ~$50) without knowing how much they’ll end up paying. For this reason, and as you saw in the spreadsheet above, an average buy-in (and extensive prior research to get that number!) is your friend. Always overestimate the total price. Set a firm cutoff for deposit refunds (cancellations). This may cause some issues with people who cancel after that date, but that is what a deposit is for. Having a little extra cash on hand can be valuable for big trips.

Part of the fun of trip planning is choosing the accommodations–you get the final say in where the group is going to stay.

Once you have about 70% of the deposits (most will pay within the first 24 hours), go ahead and book the accommodations. It is always useful to find an Airbnb with a generous cancellation policy just in case. Check your credit card to see if there are any cashback deals for Airbnb bookings too. The owner will likely reach out to you, especially for bigger houses, and ask what the purpose of your trip is. Be honest and well-spoken, and you’ll probably be just fine. We’re college kids on spring break, our goal is not to burn down the house, and our (heavy) partying will be at the beach.

At this point, your role is to keep collecting deposits until you have filled the Airbnb. The next step is enacting a payment schedule for the remaining balance. I stuck to two payments of equal amount, with the last one being at least a month before the trip. In the event there are more deposits than places to sleep in the rental, book a hotel nearby. I had to do this for the last spring break’s remaining four members. It is a good idea to put those latest to join the trip in the hotel; early bird gets the rental. You’ll likely have to fill out a credit authorization form with the hotel so you can be charged but book it in one of the guest’s names.

Phase 3: Leading up to departure

At this point in the process, people have at least paid the deposits and perhaps made the first installment. There is some kind of shared document or website available that lists the trip information. I make sure to include the places we will be staying (with addresses), a fact sheet about payments and those attending and the area around our rental.

A financial report is a smart move depending on how transparent with the money you want to be. Trip assignments list out the property’s room layout and who is sleeping where. Some kind of seniority system should be in place to determine the order people pick spots. The FAQ is up to you, but include some common questions and answers, such as what to pack, the food situation, resolving disputes, etc.

Let’s review the trip checklist before the big day:

1. Accommodations. You’ve sourced an Airbnb (or two) that has enough room for all attending members. The house rules for each are clearly stated. Room assignments have been taken care of.
2. Transportation. While this can be taken care of offline, it is best to have a hand in the travel. Match those willing to drive with those who need a ride. Make sure to account for luggage space in smaller cars. Avoid vehicles that use a lot of gas; the Prius and CR-V were our go-tos. Suggest a time to leave that accounts for those who stop and get food or get a late start.
3. Itinerary. You’ve scouted local restaurants, bars, and attractions, and have conveyed these to the trip members or posted them somewhere accessible. The best itinerary is no itinerary, save for one or two “planned” days with the whole group.
4. Budget. Is everyone paid up? The financial report takes care of any budget questions and accommodations are completely handled by the trip planner. As I say, my job is to get you there and a place to sleep, the rest is up to you.
5. Risk Management. Have contingency plans in place for those arriving early or late, those flying in, and other travel issues. The other area to watch out for is damages, and this was the case on the last spring break. We caused about $350 worth of extra charges at the end of the trip. In some cases, you’ll need to fine one person (whoever solely caused the damage) but in others (and mine) you use the reserve funds to pay up without pestering people for more payments. As I said earlier, collecting a little more than you need can go a long way.
6. Documentation. All the trip details should be in one, easy to digest place. Answer questions before they’re asked and cover your ass as far as payment policies. If it isn’t written, it isn’t enforceable.

That’s it. Enjoy the trip. Relish in your hard work and reap the benefits (in the form of credit card points, first pick on rooms, etc). It is a thankless job but the memories are worth it.