Guide: Traveling with Groups

Traveling with groups of people can be a lot of fun, but it can also be a pain. It all depends on who you’re traveling with. Below are some tips when traveling with other people.

Be very selective of your travel partner(s): There are no “wrong types”; there are just bad matchups. For example, if you like going to museums while the other person is into 24-hour raves, that’s not the best combination. A general question to ask the other person: What was a great trip that you went on and why was it fun? Does their answer align with your beliefs?

Have a general plan and communicate it early: Everyone will be aware of what’s coming up and offer feedback.
Communicate early about:

Attractions: museums, beaches, hikes
Accommodations: Hotel preferences, Airbnb, couch surfing
Transportation: Uber, public transportation, biking, walking
Nightlife: Bars, lounges, club, none
Food: cuisine, budget, frequency, ambiance

Don’t be afraid to separate: It’s unrealistic to expect the group to stay together the entire time of the trip. If some members want to spend 3 hours drinking bottomless mimosas and the other members want to go to a museum, please let them split. Everyone will be happier after. A brief separation is much better than a petty fight.

Pay attention: Moods can change very quickly during vacation because a lot happens at once. Any group member can go from zero to annoyed very quickly. Thus, pay attention to how everyone feels to catch issues before they spin out of control. For example, everyone knows that I love speakeasies, so I usually travel with like-minded people that also like speakeasies. However, few know that I HATE fist-pumping music. During a trip, we happened to go to the one speakeasy that played fist-pumping music (only in Florida smh) and I wasn’t happy. Unexpected and minor variables can quickly change the mood so be attentive and pivot if necessary.

Smaller groups > larger groups: Traveling with a group is like juggling. It gets harder to manage as the number increases. Managing the trip itineraries, logistics, and personalities becomes more complicated with each additional person, so keep your group as small as possible. For example, when traveling alone, I can usually eat at any restaurant because there is always a seat at the bar. However, add another person, and now I have to make a reservation a couple days beforehand.