The Itinerary

Don’t Over-Schedule

If I’m hosting the trip, I’ll usually have a few daytime activities selected in advance, but I don’t plan each day ahead of time, instead gauging the group’s energy level and making a plan at the start of each day. If an activity doesn’t feel right, ditch it. Don’t worry about squeezing too much into these big trips. Avoid scheduling anything too early in the day, especially if you’re taking advantage of any local nightlife.  —AB

I’m not a huge planner by nature; I like to feel out a city and let my gut lead the way—which I fully admit can be a challenge when big groups are involved. The key is balance and flexibility; think through a few activity options for each day so that people don’t feel totally clueless about things to do, but don’t overschedule so much that everyone feels obligated (read: resentful) to follow a rigid checklist. Don’t overthink it; if people aren’t feeling any of the museums you picked out, swallow your pride and open your web browser. Google is everyone’s friend; you have to work really hard to be bored in a new city nowadays. —EGH

“Good For Groups”

Lounging by a pool, beach days, renting a boat, and workout/yoga classes are good activities for big groups. Avoid vague plans like “explore the neighborhood” unless it’s explicit that people are good to split off and do they’re own thing.  —AW

Needs vs. Wants

Put together a list of what you can’t go without doing and a list of what it would be nice do if you had extra time. Think of it as a needs versus wants strategy. It helps you plan out your days around certain activities or stops and gives you plenty of suggestions on how to fill in your free time. It also makes it easier to divide into smaller groups when the people’s choice doesn’t come to a majority. —EC

Make it Accessible

Once you have everything planned out, make sure the group can easily access the itinerary. I find the best way is to make the weekend plan screenshot-able, so they can just go into recent photos and don’t have to search through email for it. If people don’t have access, you’ll just get barraged with questions constantly. You don’t need to write out every bar you want to hop around to in the itinerary, but you need to have that list somewhere readily available. Someone’s got to lead the group and it’s probably going to be you! —AW

Money

Communicate

Be as open as possible. Forthrightness around money is really refreshing, and will help the group feel that they can share their preferences and limitations freely. —CS

If budgets aren’t the same across the group, it’s worth planning one activity a day, whether it’s a meal or otherwise, where everyone will be together and with the full understanding there’s no judgement for going your own route. —EC

Set Rules; Use Technology

Money-wise, I think you have to just be compassionate about what people are comfortable with financially. Try to plan things at diverse price points, and make it known that it’s totally OK to skip stuff if there’s an activity they don’t want to participate in. Have one person pick up the tab at restaurants and other group activities and calculate cost-splitting at the end. Also, you must get everyone to download Splitwise before the trip so you can seamlessly divide expenses (which people can individually customize and input as they go). Another thing to consider: decide (and make it known beforehand) whether or not everyone else is covering for the bride’s expenses. I hate this part, but it’s an unfortunately reality. —AW

Group Dynamics  

Schedule Breaks

I always have a fear of getting sick of the people I’m traveling with and vice versa, so I would make sure that people feel encouraged to go out and explore on their own from time to time. Scheduling in some intentional breaks in between all the ~intense bonding~ that’s sure to be happening will serve everyone in the long run. —EGH

It’s OK to Opt Out

For the benefit of the introverts in particular, make sure everyone in the group knows that opting for me-time as needed is okay. The cure for any tension around budgets or partying is an atmosphere where peer pressure isn’t a factor and motivations won’t be picked apart. Self-care is group care, too.  —CS 

It Doesn’t Matter

Though you are responsible for planning, you are not responsible for managing everyone’s emotions. Let’s be real: The only thing that really matters at the end of the day is what the bride wants, and no one else. Beyond that, just think of how you can make the most of your chosen destination and keep the itinerary flexible.  Keep that perspective and let people do and feel as they please.   —AW