What You Should Know Before Booking a Vacation with your Friend

In the words of George Costanza from Senfield, “…trips are relationship killers!” This can be extremely true!  Taking a vacation with someone can make or break a friendship and you should not take the decision to travel with someone lightly.

When it comes to traveling with friends, I’m sure the first thing you think about is sharing a room or spending long periods of time together, but what about before you even get on the plane? There are multiple things that can cause a friendship to sink or swim prior to arriving to your destination….if you even make it there with that friend.

My best advice when you decide to book a trip with a friend is to use the following guidelines:

  1.  Purchase travel insurance:  When you are traveling, you should always purchase insurance no matter what.  Travel insurance has many benefits including protecting yourself from your friends in case they decide to flake out on the vacation at the last moment.  Even if you are super close with your friend(s), you never know what might happen and you don’t want a canceled trip to ruin the friendship or your bank account.
  1. Understand the phrase “based on double occupancy”:  When booking an all-inclusive package or a cruise, many times you are quoted a price based on double occupancy.  That means the cost that you are going to pay is based on two people staying in one room. I have had many clients believe that if their roommate cancels they can just continue on the vacation at the same price, but this is not the case.  If you are planning to continue alone, you have to be prepared to pay extra for a single occupancy room. So, if your friend cancels, you have two options–pay the extra fees associated with traveling as a single or cancel your reservation as well.  If you did not purchase travel insurance (see above), you could lose money because of someone else’s decision.
  1. Upfront communication is crucial:  Have an honest conversation with your friend(s) prior to paying a deposit and confirming your reservation.  Make sure all parties understand that once a deposit is made, everyone is making a commitment to each other—a commitment to go on the vacation.  If you feel that you cannot have a verbal conversation, then send them a copy of my Girls’ Trip PSA Video and lighten the mood with a funny video.  If those options aren’t available, refer back to tip #1–purchase travel insurance (I cannot emphasize this point enough!).
  1. Stay in communication throughout the process:  It’s important to stay in constant communication with the person that you are sharing a room with to ensure they will make the final payment.  I have had worried clients call me and ask if their roommate has made any payments, which is unnecessary stress on them.  Instead, have regular check-ins to make sure everyone is on the same page and scheduled to pay on time.  Let’s be clear—no one is trying to count anyone’s coins.  However, when your trip depends on the actions of another person, I think you have the right to be updated on the payment status.  You do not want to be blindsided and find out that the person you are sharing a room with plans to cancel or cannot pay. You know what helps you avoid this worry and stress? Yup, travel insurance. ☺ 
  1. Recognize the red flags:  With over a decade of travel agent experience, I have learned to recognize red flags from clients who have the potential to cancel their vacation.  Here are some red flags that you may have selected the wrong travel companion and may be in trouble come balance due day:
    1. They have a hard time coming up with the initial deposit.  This is the ultimate red flag!  If your friend cannot afford to pay the deposit, at the time the deposit is due, and you have to pay it for them–this is an indication on how paying the balance will be at the end.
    2. They are not making any payments in between the deposit and the balance.  This is a sign that your friend might not be going on the vacation.  I say might because a lot of people just pay the lump sum.  However, I have seen so many people unable to pay that lump sum on balance due day because they have never made any payments and the sum is too great for them.
    3. They do not care to engage with you in talks about the vacation prior to the date of departure.  If you try to make plans or suggest ideas of what there is to do at the destination and your friend ducks and weaves like Steph Curry, this could be a sign that they are not 100% sure they are going to be able to go.

Up to now I’ve been speaking from the point of view of the friend that is definitely planning to take the vacation (and has made all the pre-payments!).  On the other hand, if you are the shaky friend who might bow out, give your friends the respect they deserve by telling them prior to the balance due date that you are not going to be able to travel.  This gives them time to decide what to do and make other arrangements.  Don’t be disrespectful and cancel on the day the balance is due.  That is not cool and it’s not being a good friend.

I’m a firm believer that you should know upfront if you can afford to go on your vacation or not.  You know what you can afford, and if you don’t, I always provide my clients with my free downloadable payment plan calculator to assist them with paying for their vacation packages. Sure, sometimes life throws you a curveball that affects your finances and you don’t really have a choice but to cancel, but any quality friend will understand that (and be smart enough to have travel insurance!).

I’ve been a travel agent for over ten years and it breaks my heart whenever I see someone miss out on a vacation because they selected an unreliable roommate that led the person to believe they would travel with them. Don’t end up being either of those people because not only will you lose a great travel experience (and possibly a big chunk of change), you’ll lose a friend as well. 

At the end of the day, we know our friends.  We know which ones are organized and financially reliable, and which ones aren’t. Therefore, choose the friend(s) you can count on when it comes to sharing a room.  When you are on the same reservation, everyone’s actions affect the others.  Choose your travel companion wisely and of course, choose travel insurance.

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