Too Many People
It's tempting when you're going on vacation to want to take all of your closest friends and family members with you so that they can share the experience. Sometimes having a few extra people along can heighten the experience, especially if you all share the same goals and expectations for the trip, there is definitely an upper limit above which extra people can make the trip more stressful.
One of the reasons for this is that people rarely do have exactly the same goals. Even when two people go somewhere together they usually have slightly different ideas about what they want to see and do, and how they want to do them. With only a handful of people these differences can be managed, but as groups get larger each individual may end up spending less time doing the things they chose to do and more time going along with what others want.
Larger groups also make the logistics of a trip more difficult: it's harder to find seating in restaurants for large groups, you need larger or more vehicles to get around, etc.
If you do decide to take a trip with a large group of people, you have to remain very flexible and be ready to break into smaller groups as required. For example, one day my girlfriend and her family went shopping (which I had no desire to do) while my family and I went for a hike (which her family didn't want to do). We were essentially on different trips for that day, but we still met up in the evening to hang out and talk about the experience.
Not Expressing Your Desires
I suppose in general this falls into the "lack of communication" category which is a killer in any trip, but more specifically I'm talking about people who have something in mind that they want to get out of the trip, but never mention it during they actual planning. They go along with other people's plans assuming that other people will want to do the same things, and then are disappointed when it doesn't happen.
If you have a specific thing that you really want to see or do in the place you're visiting, bring it up with the people you're going with. Even if they don't necessarily want to do that themselves, they will be aware of what you want, and are more likely to try to accommodate it. They may not even have considered that as an option and may think it's a great idea, especially when it's something that differs from the mainstream sights and activities for the area. Even if they don't want to join you, it may be easier to plan in a bit of time on your own if others are aware of you plans.
Trying To Control Everyone
Anytime you are travelling with someone else, be it one person or a group, you are not going to be able to do what you want 100% of the time. That's simply the price you have to pay to have company. Trying to force people to do what you want to do when you want to do it because it's "your vacation" is a recipe for disaster.
Unfortunately in every group there seems to be one person who is more dominant and outspoken than the others. It may be difficult to notice right away if that happens to be you. If it's somebody else, it will probably be glaringly obvious.
One way to avoid this issue is h allowing each person to pick an activity in turn. If you just went to see something that person A really wanted to see, giver person B a chance to say what they want to do, and then person C. You may not agree with their choice of activities, but you have to keep in mind that some compromise is necessary to make your trip successful.
Having Travel Plans That Are Too Rigid
While it is a good idea to do a bit of research before hand about the area you're going to and have some activities in mind that you want to try there, I don't think planning your trip down to the last detail improves the experience. This is especially true when travelling with other people, as the more people there are the more likely it is that someone will notice something new they want to try that they didn't think of, or that they want to spend more or less time somewhere than they initially thought, etc.
That's not to say that you should just set off on a trip without any idea of what you're going to do while you're gone - this can lean to sitting around saying "I dunno, what do you want to do?" It's good to have an idea of the range of things you might like to do, but being flexible in your planning will make it easier to adapt as things come up.
These are just a few of the issues that can come up when travelling in groups, and the list is obviously not exhaustive. The key to dealing with many of the issues as they come up is the same as dealing with interpersonal issues in any environment - communication and compromise. You have to realize that they people you are travelling are not the same as you, and be able to take that into account. Sometimes this may mean compromising in regards to what you want to see and do. If you feel these compromises aren't worth it, then consider that you may be better off travelling by yourself or with different people.
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