I never used to like travelling in larger groups, but the more I do it, the more I realize what a great opportunity it is to have fun, make some memories, and bond with family or friends. The key is choosing the right people. The key is to not invite people that are at complete odds with your travelling style. The best co-travelers are good-natured, adventurous, compromising and have the ability to be independent.
Once you have your people, you then need to get everyone’s buy in on the destination. If things go wrong, you don’t want the blame to land on one person’s shoulders. Whether it’s a villa, all-inclusive vacation, or cruise, make sure everyone voices their requirements in advance. In our case, we wanted a villa in Tuscany that stayed within a certain budget, had a pool, Internet, and a separate bathroom for each couple. Once we had the list of criteria, everyone going on the trip was invited to research and submit an option. We then presented the various choices to each other and voted on the one we, as a group, wanted.
A month before we left we had a dinner meeting to get everyone in the same room to discuss preferences and approaches. After 45 minutes of discussion, it was very clear who wanted to do what, what time folks wanted to get started and whose tastes more or less synched up. We left the meeting understanding the logistics, like how we would choose bedrooms (drew cards), split groceries (evenly), and knowing that we would not over-plan the days. We all agreed on one or two must-dos and assigned someone to make the required reservations.
It is actually very important to make reservations when travelling in a group. Restaurants often have trouble quickly accommodating large walk-ins, which in our case was eight. Plus making an advance reservation takes the humming and hawing factor out of picking the restaurant, which can be a real drag when you are hungrily roaming city streets. Some attractions, like the wineries in Tuscany, also require reservations for groups.
Other tips:
Don’t feel like you need to move en masse all the time, and allow for unscheduled time and/or alone time. There is no rule that says a group that starts the day together must finish the day together.
Share your knowledge. Almost everyone in our group had done a bit of research, much of it reflecting their own interests, so let other people take the lead. One of our friends had researched spas, something I would not have thought of in Tuscany. Yet it turns out that the bathing rituals are a big part of the culture: spending hours soaking, steaming, and relaxing. It was a great end to one of our days.
Let people play to their strengths. It quickly became clear who had the best sense of direction, who read maps well, who could speak some Italian and who could fire up that 300-year-old pizza oven! 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 and everyone feels useful and valued.
Other things to consider, that we didn’t do, make a private Facebook group (for the planning stages and to avoid email chains that can get lost), create a ‘chore list’ (no one likes dishes), and as part of the planning discussion, make sure you are clear on deposits and discuss what is an acceptable reason to cancel and not have to pay your portion of the deposit and final bill. We had three friends cancel, all for reasons out of their control. It can happen and we all agreed on how to handle. But worth discussing in advance.
