Group Vacation Advice

This idea popped into my head as I was reading about a fellow poster’s upcoming trip. And while he seems to have things under control, I realized that other folks might have less experience with group vacations. As someone who has endured (and learned from) a lot of vacation-related grief, I figured it would be fun to jot down some notes. And who knows…maybe I can spare someone else some heartache down the road.

When I say “group,” I’m not referring to a husband, wife and their kids. I’m referring to families with adult children, in-laws, and the like. Or it could be a group of adult friends. I’m sure most of the below advice would still apply if kids are involved. But advice about how to best travel with kids probably warrants its own thread.

TL;DR version: While vacations are meant to be fun, they are also high-stakes endeavors because large amounts of time and money in play. The keys to an enjoyable group vacation are robust pre-communication, planning, and grace. Here are some specific tips I thought of. I’m sure other posters will chime in with other thoughts.

1. Don’t force a budget or timeline on anyone: This stuff stresses people out, and for good reason. How people spend their time and money can be a very personal and touchy matter. One member of the group might be making $350k/year. Another might be a public school teacher. So it’s not a great idea to tell the teacher that they need to get on board with a two-week trip to France and Italy in October staying in five-star hotels. The bottom line is that you want everyone to be agreed upon the general budget and timeframe. This is probably the most difficult part, as it requires good communication and even some diplomacy.

2. Acknowledge sacrifices: when a group vacation is planned, it is almost inevitable that at least one person is making a significant sacrifice to make it work for the greater good of the group. Maybe the chosen timeframe is a busy season for them at work. Maybe it’s a husband and wife who haven’t had the chance to take a nice vacation on their own in a while. Maybe someone is dipping into their savings to afford it. Regardless of what it is, be sure to acknowledge those sacrifices. Treat them to a nice meal. Don’t be a jerk if they need to log-into their work email for a few hours one day. Buy them a bottle of wine.

3. Respect differences: People are…well, different. And the word “vacation” may mean something very different for different people. One person may want to spend all day exploring the sights and history of a city. The other might want to chill by the pool and relax. And there’s nothing wrong with either! Maybe the person who wants to chill just had an insane month at the office. So don’t try and force a singular itinerary on the group or lecture everyone on the “proper” way to spend a vacation in a given locale. Instead, plot out the major items (flights, cities, hotels, etc.) and then have some discussions about what people would like to do each day. When common themes surface, great. Turn those into group days. Otherwise, let people naturally flow with want they want to do. A good tip is to always have a plan to meet up for drinks and dinner each evening. That ensures the group spends at least some time together each day, and it’s a great way to swap stories about what everyone did that day.

4. Be flexible and gracious: Big group trips inevitably throw curveballs at you. A flight gets cancelled. Someone gets sick. Someone is too worn out to make it to the fancy restaurant that was planned for that night. Be ready to roll with the punches. Nothing will sour a trip faster than getting into a petty argument over something that is inconsequential in the big scheme of things.

5. Pack light: This one is more applicable for multi-destination trips, like Europe. People always underestimate how burdensome and stressful it is to lug around tons of heavy luggage. Even simply getting it from the curb up to the hotel room can be a hassle. And sometimes, it’s the little things that can ruin the vibe. Try to keep your packing to a rolling, carry-on and backpack. And gently encourage everyone in the group to do so. Yes, it’s tougher to plan out, but it will pay dividends in the long run. When everyone can saunter along quickly – whether it’s at the airport, boarding a train, or navigating an unfamiliar city – it makes everything go that much smoother.