On a recent combined business/leisure trip to London, I ended up in a large living room with a group of more than 20 young women who were trying to plan their day in London. Different travel styles emerged almost immediately: Captain Planner was making written checklists ranked by priority, with Definitely's, Maybe's, If Possible's and Maybe Next Week's.
The Tourist was listing off obvious landmarks and looking up prices for bus tours. Eeyore the Traveler was bemoaning every idea as boring, too far away or likely to have long lines, and wondering aloud if they should just stay home and read. The Laissez-Faire Traveler was sitting on the couch flipping through a magazine, saying every so often, "You guys are crazy; just pick one thing and then figure it out after you get there." The Shopper had but one idea: go into town, get a drink and go shopping.
These were just the stylistic differences; the choices of preferred sights offered proof that there's no accounting for taste. At one end of the spectrum was a murderous schedule of high-culture museum visits; at the other end of the spectrum was a schedule of visits to the sites of famous murders. In between, just about every London landmark ever to grace a guidebook was mentioned at least once.
There is no reconciling someone who wants to go to the Tate with someone who wants to take their kid to the Peter Pan statue and playground. It will never happen. Sure, some kids would put up with Miro mobiles at the Tate Modern, but not the Tate proper.
Similarly, there are people who want always to be with large groups of people, and others who would rather travel in smaller groups, which they may find more manageable for reasons logistical, emotional or financial. If you find yourself trying to reconcile a dozen or more diverging interests, here are my tips for keeping the peace and the pace when traveling with a large group of friends, family, colleagues or acquaintances (or even frenemies, as the case may be).
1. Talk it out
The exercise of having everyone more or less in the same room, where preferences and approaches could be aired out, really seemed to help this group. After 45 minutes of discussion, it was very clear who wanted to do what, what time folks wanted to get started, whose tastes more or less synched up, and which folks really wanted no part of the whole thing. Getting these right is really the heart of traveling together.
Making sure everyone had a voice — or at least enough air to get some words in — was an important part of the exercise; despite their different styles and energy levels, everyone made some kind of positive contribution to the discussion. Even Eeyore was helpful, forcing everyone to be a bit more realistic (and it turned out rightfully so) about things like transit times and crowds.
2. Share your knowledge
Almost everyone in the large group had done a bit of research, much of it reflecting their own expertise and interests, so that when they all started throwing out ideas and suggestions, in the aggregate it was like having the ultimate guidebook writer sitting in the room with you outlining your perfect itinerary.
3. Have your own must-do or must-see
You don't want to drop a few thousand dollars on travel, lodging, admission and bruising exchange rates only to get on a plane home having failed to do the one thing you really wanted to do. Although I do sometimes recommend it (Return trips: Why the second time's a charm), few people take repeat vacations to the same major cities — so if you have a bucket list item that needs crossing off, don't fail to make it happen.
On this trip, I was traveling with my family, and our 4-year-old wanted to see the clock that Peter Pan lands on (Big Ben, obviously), as well as the playground with the ships and teepees — but he also wanted to see the statue of Peter Pan. We scheduled the statue last, as it seemed the least compelling of the lot, and when a typical flash London rainstorm rolled in toward the end of the day, we never made it.
He didn't seem to mind, but when he got back to pre-school a few days later, the first question the kids asked was "Did you see Peter Pan?" Despite having seen the clock and the ship, he couldn't quite answer yes, and it was a (very) small disappointment, I could tell.
4. Let folks play to their strengths
As you get underway, it will become clear who has the best sense of direction, who can read maps fast and well, who is happiest asking questions and directions of strangers, who can speak a foreign language best, who excels at handling money, etc. Let those people do those jobs with which they are most happy and at which they are most competent. This way the workload gets spread around, everyone feels useful and valued, and things actually get done.
If someone falls into one of these roles, encourage and thank them for it; it can be difficult and thankless work figuring out train schedules or restaurant bill portions for an unappreciative mob.
Of course, in a large group there is always the risk that a "control freak" wants to do everything and make every decision, but I have also found that the large numbers can tend to lessen the ultimate impact of these folks.
5. Speak up, but listen well
As during the planning phase, once you are underway make sure everyone has a voice in what happens during your ambles, and be respectful of their traveling styles.
You will need to speak up if you want any say in the proceedings. In particular, if you have something that folks need to know — you are calling home at exactly 2 p.m., or you are short on cash — you need to share it. Conversely, pay attention when someone has a special request or requirement for meals, breaks or similar needs. For example, you will want to know if someone in the group is a vegetarian before you insist on eating at Maison du Boeuf or La Casa de Vaca.
Not everyone necessarily needs to have an equal voice. If one person likes to be out front at all times, and another person likes to ride the caboose and simply follow along for the ride, it is often best simply to let them do so. Let the conductor steer the train, and the caboose rider catch the sights as they go by. Both will likely be happy in their chosen roles.
6. Don't be over-ambitious
The single most common error in traveling with a group is to set too strenuous a schedule; even small groups are not as nimble as you and a bud can be, and you would do well to realize this up front. Setting yourselves up for, and then trying to execute, a forced march through countless sites with a large group is represented as a ring of Dante's Purgatorio, if I recall correctly.
7. Break ranks as necessary
There is no rule that says a group that starts the day together must finish the day together. On several of our outings, we started out with other folks, saw a couple of things in which we all had interest, and then split up. In one case, we didn't see the other people for a few days after that. No big deal; we had a great morning together, and a great afternoon apart.
8. Have an alternate plan
On this score, you should have your own plan for an alternate activity or route in case the scheduled itinerary starts to collapse, folks get combative or you realize you want to move at a different pace than the group. In the end the quality of your trip is in your hands alone, and you need to accept that responsibility.
9. Look for group discounts
If your final group is large enough, it may qualify you for considerable discounts at many attractions. These discounts are often best arranged or even purchased in advance, but if this isn't an option, it is simple enough to ask.
10. Try trip planning services
For big trips, you might consider a travel planning service that walks you through many of the steps above; check out Triporama.com, TripIt.com, TripHub.com, Groupon.com, LivingSocial.com and PayDivvy.com (for divvying up expenses). There are apps for some of these as well.
In the end, while the original intention was to travel as a roving horde, the large group sitting around the living room ultimately split off into a handful of smaller groups — pretty much the same individuals who were most comfortable at dinner together, or when walking around, or when picking roommates. That is, everyone went for their comfort zone, which has its own rewards. But the living room exercise was hardly for naught; on multiple occasions over the next few days, the groups stumbled across one another unexpectedly in pursuit of common interests, and the recombined groups showed a powerfully increased energy level. Everyone got to do what they wanted, sometimes on their own, sometimes together — and always the better for it.
For more advice, see 18 ways to keep the peace with your travel companion.