Recently, I took a weekend ski vacation to our nearby mountain – Whistler. As you know, the trip turned out to be a complete success, however it certainly did not go according to plan. My experiences in the lead up to the trip really got me thinking about the difficulties of planning a trip with your friends, particularly where money is involved. It seems to me that everyone could benefit by establishing some common courtesy rules when planning a group vacation. We ended up losing three friends in the process and I don’t wish that on anyone.

The Background

Since the trip to Whistler was a birthday present, the gf decided it would be great if we could bring up a few of our friends and make a weekend out of it. So, we invited a few friends and went about planning the trip. The friends that we chose were great to hang out with, but have a very different philosophy than I do when it comes to money. In the end, the process made us so uncomfortable that we decided to go it alone and plan our own trip. We haven’t spoken since.

Situations like these are completely unnecessary and avoidable and I want to make sure everyone has the tools to prevent this from happening to you! Reflecting back on the experience, I believe that the following rules should be applied when money is involved between friends and offer the following examples of how it went wrong for me.

Agree on key parameters

Defining what you want the trip to look like is key. Will this be a trip where 10 people pile into one hotel room, or will you book a private condo with enough beds for everyone? Some friends will like the idea of cramming into one room and splurging on entertainment instead of sleeping quarters.  Other friends may prefer the luxury of a hotel room or want specific luxuries, such as a hot tub.

What went wrong: We did not agree on these key issues up front. Our friends ended up taking the lead on booking accommodations and booked an expensive private rental, with hot tub and private bedrooms for everyone rather than the much less expensive, but admittedly more crowded, Living Social hotel deal that we found.

Designate a lead planner

There is nothing more confusing than having five different people trying to make one decision. Identifying a leader early in the process will help avoid confusion and provide for a clear flow of information.

What went wrong: The gf began planning the trip, but then left the accommodation planning to our friends. Our friends did not live by the first rule!

Don’t ask to be repaid before the trip

Just as you designate a lead planner, often it is easier to have one person pay all the major expenses and then be reimbursed later. This lets all of the expenses be divided up fairly, assuming you have already implemented the first rule. Do not expect to be reimbursed immediately, especially if there are a lot of people coming!  It’s just not realistic.

What went wrong: Our friend offered to put the charges on their credit card, and then expected to be reimbursed immediately because they claimed their credit card bill was due a week. If you carry a balance on your credit card and will need to be paid right away, it’s best not to put more expenses on your card.

Treat your friends like friends

The most important rule when planning anything with friends is to make sure you treat them like friends! In order to apply the rules above, there needs to be a base level of trust and maturity between all parties. In our experience with this trip, we found out that our friends were not really that great of friends at all.

Please share your stories below if you have additional rules or stories about planning trips.