The Consummate Traveler – What to Consider Before Vacationing with Friends

By Michele Goncalves
Michele Goncalves
Michele Goncalves
April 30, 2015 Updated: April 30, 2015

The special bond that we share with our friends is a beautiful thing. They are there in the good times, bad times, and sometimes everything in between. Nevertheless, no matter how many times a day you text or how many dinners and movies you’ve experienced together, there is nothing like going on a vacation together to see if you are truly compatible and can stand the test of time.

This very subject has actually touched me personally. Years ago I became good friends with someone who I decided to meet in Europe for a week-long vacation. All in all things generally went well, until we needed to talk about money. For simplicity sake, I had arranged all of the details and made the reservations, some of which I needed to pre-pay. When all of the costs were presented at the end, there was a lot of complaining and penny pinching. Needless to say, we have not gone on another vacation since.

I would like to share a few critical discussion points to consider before venturing out on an excursion with your BFFs:

Understand each other’s goals – Every individual participating in a vacation has a personal goal in
mind regarding what they want to get out of it. For one it may be to get much needed rest by relaxing on a beach doing absolutely nothing. Yet for others, it may be to explore every inch of the island and sign up for all the activities the resort has to offer. It is extremely important to have a vacation planning discussion ahead of time to communicate what type of vacation is desired before booking any reservations or deciding on a final destination. If tensions start to rise during this process, it is a good opportunity to rethink it.

Estimate Budgets– Money is a touchy subject in any relationship, including friendships. I can’t stress
enough how important it is to do your homework and get a realistic budget of what the total vacation costs will likely be before booking any arrangements. This includes estimating mundane things like gas money, train fare, tolls, and museum entrance fees. If you need guidance on this, use an online travel budget calculator tool such as the one on PRACTICALMONEYSKILLS.COM. Also, openly discussing and agreeing on when the money will be due, such as pre-payments versus paying after the fact, and who will pay for what is critical. If one friend has a great job, while the other is struggling to cover their monthly expenses, the amount and timing of the expenses can be a significant issue.

Can you separate? – If during your vacation planning discussions you have determined that you and
your travel companions want to accomplish very different agendas, make sure everyone is open to the idea of splitting up and going their separate ways. This approach will let everyone’s needs be met. Otherwise, someone will be going home disappointed. I once went away with a friend who refused to leave my side for one minute. When I turned down the idea to participate in a class at the resort because I wanted to sit by the pool, my companion became upset and sulked the rest of the day. One way to avoid this is to come up with a daily itinerary so that everyone can clearly see what each individual is up to and expectations are clear.

As always, I wish you the happiest of travels!

*Image of group of young friends enjoying meal in outdoor restaurant via Shutterstock