The Consummate Traveler: The Essential Checklist for New Travel Companions

April 27, 2013 Updated: January 25, 2019

Have you ever gone on vacation with a friend or family member, only to realize that you are complete opposites? Maybe you enjoy early morning hikes, and they want to sleep in until 11 a.m. Or, you prefer to explore fine dining, while they are looking for the cheapest food they can get from street vendors. If you are contemplating a vacation with individuals you have never gone away with before, this article is for you!

I remember a personal experience with a close friend many years ago. Although we had vacationed together before, on this particular trip she surprised me and decided it was best to sleep in late as a way to save money on food! As a result, I felt a bit constricted. In order to make sure your next trip is enjoyable, here are my suggestions for pre-trip planning to maximize enjoyment and minimize disappointments for everyone involved:

1. Make a top five list: Have each person (or family) in your group make their top five “must do” list for the location you are visiting. This is especially helpful if there is a large group of individuals or several families traveling together. Share your list with the entire group so that everyone can clearly see what is on everyone’s wish list. This helps to set expectations for the entire party.

Checklist for Travel

2. Discuss a daily schedule: I think one of the most important things to understand about new travel companions is their daily schedule while on vacation. By this, I mean wake-up times, meal times, and bedtimes. This is especially relevant if you are going on vacation with someone you work with. What people do Monday through Friday may be totally opposite what they hope to do on a vacation. If your companion wants to sleep in and relax until noon each day, this gives you the ability to get in your workout or explore something on your own “must see” list each morning without hurting the other’s feelings.

3. Discuss the option to separate: I have been on a vacation with someone who refused to do anything without me. Even though we were on a resort that offered different activities, they didn’t want to leave my side just because I didn’t want to join an activity they really wanted to do. This made me feel boxed in. Once you share your “top five” list with each other, see what you have in common and see what interests you individually. This is the perfect time to discuss the possibility for an option to separate for a day or a few afternoons during your trip in order to tackle everything on your wish list. If the other person does not want to separate, at least you know ahead of time and can compromise on an alternate plan.

4. Discuss food budget expectations: If you are not headed off to an all-inclusive resort where food is 100 percent covered, meals can be a huge part of the total expenditure of going on vacation. It is ideal to do some research by looking up a few local restaurant menus online to understand how much things cost. Approach your travel companions with these figures and discuss what a reasonable daily meal budget may actually look like. This will help you talk real numbers and set food related expectations.

As always, I wish you all the happiest of travels!