Mistakes People Make On Group Trips

Group trips are a great way to explore a new destination and make lifelong memories while connecting with loved ones. But with many different personalities and preferences at play, issues can arise.

“Most of the time, bad experiences on group trips aren’t a byproduct of going on a group trip,” Wendy Diep, a co-founder of the group travel app Let’s Jetty, told HuffPost. “It usually stems from poor planning, lack of communication and unmet expectations. But remember, it doesn’t have to be that way.”

To help make group travel a more enjoyable experience, HuffPost asked Diep and other experts to share some common mistakes that people make on these types of trips.

“Most people prefer to travel with loved ones, and post-pandemic, people are craving human connection and real-world experiences more than ever before,” Diep noted.

“Avoiding talking about money is a big mistake,” Diep said. “With a group, you’ll have people who have different spending styles or budgets. I have friends who love to have every meal out at bougie restaurants while they travel, while I have friends who can’t spend that kind of money. Not discussing it upfront will lead to awkward or uncomfortable moments on the trip, which really sucks when everyone’s already spending their hard-earned money to be there and have a good time.”

Before embarking on your trip, find out everyone’s budgeting priorities and preferences. Choose accommodations and meal options accordingly, and keep people’s financial needs in mind throughout the trip ― for instance, when you’re figuring out how to split a dinner bill after some people had multiple courses and drinks while others just ordered salad.

“Ask everyone how much they are looking to spend for the entire trip, including food and activities,” said Phil Dengler, a co-founder of travel website The Vacationer. “Traveling with people who have a high budget is easy, but you will have to do a little more work if you are with more frugal people. If your budget is limited, figure out any potential splurges that will make everyone more comfortable.”

“Not having a plan is the biggest mistake you can make on a group trip,” said Madison Pietrowski, the director of brand for the U.S. at the travel platform GetYourGuide. “Book your activities in advance! It’s important to have a plan for each day when dealing with a large group, or else you’ll feel like you’re herding cats.”

She recommended booking at least one or two planned activities for each day, but also familiarizing yourself with the cancellation policies in case you need to make changes. Keep the group informed of the proposed itinerary so that everyone has a chance to give their input.

“Plan interactive experiences that everyone will enjoy,” Pietrowski added. “Does your group like to cook and eat? Are they adventurous? Into history? Personally, I’d suggest a cooking class because it’ll get the whole group involved and take one lunch or dinner reservation off your plate.”

At the very least, snag a few meal reservations because it’s more difficult for a large party to get a table at a restaurant as walk-ins.

“When I am traveling with groups larger than four, I usually book dinner reservations for each night just so we have something,” Dengler said. “I’ll share the reservations with the group, as well as a few alternative options, and adjust as needed.”

While structure and advanced planning are important for group trips, resist the urge to go overboard with your schedule.

“Planners often go in thinking they need to sort events for every day and every hour, otherwise the trip will be a bust,” said Suzie Palma, another co-founder of Let’s Jetty. “But the reality is, your group might want time to hang back and catch up with each other.”

She recommended giving people the ability to opt out of certain structured activities and leaving free time for rest. It’s natural to get carried away by the excitement of exploring a new place, but you don’t want everyone to feel exhausted and cranky by the end of the day.

“Plan for breaks in between activities within your schedule, so that everyone has a little bit of downtime and can get a snack or just relax,” Pietrowski said. “Also, think about the weather and the types of activities you’re booking. If you’re traveling somewhere that will have hot temperatures, consider booking a museum activity or other indoor tours when the time of day gets very hot. Save the outdoor activities for the early mornings or evenings.”

“It’s a group trip. You’re going to be spending the bulk of the time together, so it’s OK if groups split off or people want to do their own things for a bit,” Diep said. “It’s everyone’s vacation. Just make sure to establish the main things that people are going to be doing together. You will still have plenty of quality time together!”

Just as it’s helpful to build in unstructured time for people to rest, the group can also benefit from a little space here and there. Many folks are introverts who need a occasional time apart from others, or you might have someone in your group with a very niche travel goal that they’d like to pursue on their own.

“While group activities are essential for bonding and shared experiences, it’s also important to respect each other’s need for personal space and downtime,” said Lisa Chen, the CEO of the company ToursByLocals. “Building in some free time or optional activities allows individuals to pursue their interests independently and recharge as needed.”

Leaders tend to naturally emerge in group settings, but that doesn’t mean they should be forced to do all the heavy lifting in preparing for the trip.

“Help out your planner friend where you can,” Diep advised. “Most of the time, the responsibilities fall on one or two people, and it’s a ton of work. Volunteering to do research or book something goes a long way in saving them time or stress.”

In addition to offering help, she also emphasized the importance of acknowledging the main organizers. Consider buying them a thank-you drink to recognize their hard work.

“And on the flip side, as an organizer, sometimes you think you have to do it all, and that will lead to stress and exhaustion,” Diep added. “Don’t be afraid to delegate or ask for help! Sometimes it’s not poorly intentioned; others who don’t typically organize or plan trips may not realize how much you have to do, but when asked are willing to help.”

“A common mistake made when planning a group trip is not discussing expectations for the trip,” said travel guide Tonia Hope. “There are many important aspects that people planning on going on a group trip don’t discuss before booking and planning that really can worsen the experience.”

In addition to budgetary and dietary restrictions, she recommended asking your travel companions what type of travelers they are ― do they prefer lounging by the water and eating at hotel restaurants at an all-inclusive resort, or do they want to explore different neighborhoods and fill the itinerary with lots of activities? Just because someone is a good friend of yours doesn’t mean that you can assume your travel preferences and styles are fully aligned.

“Some people may want to indulge in outdoor adventures, while others may want to explore the foodie scene or catch up on rest and relaxation,” noted Nicole Martinez, another co-founder of Let’s Jetty. “Properly setting these expectations ahead of time will allow everyone to plan for these activities together or enjoy on their own terms. Either way, asking this question upfront will allow the group to collaborate on a vacation everyone can enjoy.”

“Shared costs are at the heart of most fallouts and arguments during group trips,” said Laura Lindsay, a travel trends expert at Skyscanner. “Forgotten pledges to pay you back later can quickly descend into resentment. It’s best to avoid any issues from the offset.”

She recommended having everyone in the group download the same budgeting app before the trip so that people can stay on top of shared expenses in real time. Splitwise is a popular option for keeping track of who paid for what and who owes whom.

“An interesting strategy we’ve also heard from our users is, when going out in large groups, put food and alcohol on separate tabs,” Diep shared. “They say it makes it easier to split because typically people are sharing food pretty equally, but how much people drink varies a lot and can be a significant portion of the bill.”

“Flexibility is key to accommodating the diverse needs and preferences of group members,” Chen said. “Encourage travelers to remain open to changes in plans or spontaneous opportunities that arise during the trip.”

Some of the most memorable travel experiences come from unplanned moments during the less structured parts of the itinerary. Fluidity and adaptability are key to taking advantage of exciting opportunities, rolling with the punches when unexpected changes arise, and enjoying a vacation to the fullest.

“Everyone going on a group trip should be open-minded, flexible and willing to compromise,” Diep echoed. “Even with the best planned itineraries, things come up. With a group of people, if everyone’s willing to give and take here and there, usually everyone ends up happy. And sometimes you’ll find that you had a great experience doing something you might not normally have done!”

At the end of the day, the most helpful thing you can do on a group trip is to go into it with a positive attitude and teamwork perspective.

“Things happen, conflicts can arise, but don’t [let] it ruin a whole trip if they do!” Diep said. “Be direct, have a conversation and talk through it. Remember you’re there to spend time together and have a good time! And most likely, these experiences end up being funny, memorable stories later.”