10 Questions To Ask Your Friends Before You Travel Together

Do you prefer an airplane, train ride, road trip, or cruise?

The answer to this question will directly impact the type of trip that you'll plan. For example, as much as I love to travel and fly, I have no desire, whatsoever, to go on a cruise. I would rather fly and go as I please, instead of boarding a ship and spending the majority of my time on it. Hence, it's no surprise that when some of my friends plan their cruises, I am not invited…nor am I offended because that's not my preference.

What types of things do you like to do when you go on vacation? 

This can vary depending on the trip (e.g., vacation, retreat, girls' trip, couple's trip, etc.). There are people who like to do as much as possible while vacationing, and there are others who like to use that time to stay in or relax no matter where they are. Then, there are those who enjoy a mixture – rest one day, explore another day, party another day. When traveling with other people, it's best to know upfront so you can plan the itinerary accordingly.

Do you prefer to stay at an Airbnb, a hotel, or a resort? 

Additionally, you may need to ask: Inclusive or non-inclusive? Room service or self-serve? How many people are you willing to share a room or a space with?

Some people only need enough space to rest their heads at night whether that's a bed, a couch, or even a roll-out bed. So, for them, it doesn't matter as much where they'll stay. On the other hand, people like me, who can be a bit of a "hotel or location snob," will research thoroughly online before booking a place to stay.

Keep in mind the budget and the destination can impact your choice, and knowing it upfront can help narrow your search.

Do you have a passport?

If you're planning to travel internationally, but you or your travel buddies don't have a passport, then you'll need to allow enough time to order one.

How long is too long to be on a trip?

This can vary depending on: 1) the type of lodging that's chosen, 2) the total number of people, 3) as well as the people you decide to travel with. For some people, two to three days may be more than enough time to spend with a certain group of people, while five to seven days could be just enough before your patience starts to run out.

What is your budget for the trip – before and during the trip? 

Although this shouldn't be considered an opportunity to meddle and find out how much money someone makes, it is important to determine if everyone has budgeted adequately for the trip. Make sure they've allotted enough for lodging, food/beverages (if non-inclusive), as well as possible extracurricular activities (e.g., shopping, excursions, tours, parties, etc.). While you may be willing to pay extra for a once-in-a-lifetime adventure or an excursion, someone else may be more interested in splurging on a spa day.

If flying, what airline do you prefer? 

Depending on everyone's home base and departure location, you may not have as much flexibility when it comes to choosing a specific airline. Nevertheless, understand that some people won't mind choosing a cheaper airline for a shorter flight. Then, there are certain people who will pay more for their airfare to allow for more leg space, priority boarding, on-flight entertainment, Wi-Fi, or better snacks.

Planned itinerary or just wing it? 

There are people who like to plan for everything, and there are those who prefer to play it by ear. Depending on the size of the group and everyone's preferences, a formalized agenda may make the most sense.

I remember when I created this elaborate agenda during a bachelorette trip to Vegas for at least 14 ladies. Although I may have included one too many activities and everyone was worn out by the end of it, the good thing about it was that the agenda helped keep us on track and on time, and everyone ended up doing a lot of things they had never done before.

Do you prefer to use rideshare, local transportation, or rent a car? 

Depending on the destination, you'll need to determine if it makes sense to rent a car, or if certain rideshare services will even be available. If you decide to rent a car or use a ridesharing service, find out if the group is willing to pitch in and help, or if you'll need to consider another option to cover the expenses.

Is there anything that is completely off limits or anything that you absolutely must do while you’re on the trip?

When someone ends up unhappy on a group trip, it's likely because they didn't get to do the one thing they wanted to do. Conversely, it could've been that they were forced to do something they never wanted to do in the first place.

So, when traveling with other people, it's important to be mindful of their desires and interests…not just yours. Of course, you can't please everyone, but by prioritizing what's most important, you can accommodate and adjust the itinerary accordingly especially if you're on a limited schedule.

For your next trip, I want #PositiveVibesOnly and positive energy for you and whoever you decide to travel with. So, depending on the outcome of the discussion, you may have to: 1) find a happy medium or a resolution that will cater to most of the group, 2) be willing to split up and do things in separate groups, or 3) exclude certain people from the trip.