Planning a Group Vacation

By Lisa Xia

The idea of sharing travel to some far-flung destination with six of your closest friends seems to be a golden opportunity to amplify a great experience. If Christopher McCandless is indeed right that happiness is only real when shared, then sharing the love of exploration with a group of friends can be appealing.

As anyone who has actually tried to actualize this vision, however, can attest, planning group travel is far from a picnic. The impossibilities of consensus breed frustration and a seemingly endless whirlwind of ongoing decisions. As a chronic solo traveler, my rules of the road for group travel are the below:

Someone has to set a date. Seriously someone just set a date: There will never be a perfect date for every last person. Someone has a party that Saturday; little Johnny’s bat mitzvah; or an aunt’s birthday. The fact is, at a certain point, one or two people will need to make the executive decision, set dates and book tickets. Having a tangible stake in the ground gives others something to rally around and plan around, even if individuals can’t make the entire itinerary. The lack of a solid date will ensure a ping pong game of emails that eventually results in all parties giving up.

Leverage assets. Who travels a lot and has hotel points? Who has car rental points? Discounted gas? By taking a clear audit of what individuals might bring to the table (for free), you can reduce total overhead costs for the group. If not everyone can bring something to the free party, agree beforehand on what those who can’t put forth some of these things can contribute to avoid any potentially awkward free-rider scenarios.

Avoid having too many cooks. Some people will have tons of ideas of what to do while on the trip. Others won’t care. Others care but shouldn’t have a contextual license to make decisions. Streamline decision-making by ensuring that your ‘musts’ are communicated with the group but agree upon the one or two people who will primarily own the agenda (if there is one at all). When I went to Napa several weeks ago, my good friend Carly, a proprietor of Yountville’s Hill Family Estate Wine, planned the weekend itinerary for our group of seven. It made a lot of sense for Carly to plan it, and we were able to contribute ancillary thing to the core plan.

Leverage technology. One of the best ancillary benefits of traveling in a group is the cost saving of buying in bulk. Four people splitting the cost of a hotel, cars, etc., is clearly better than two. When splitting bills and costs, use tools like PayPal to easily divide total cost after the trip without awkward dollar splitting.

Judge your friends. Sorry, I had to say it. Flexible people who can go with the flow are the best travel buddies. On the road, it is a certainty that something will go wrong. Don’t let one of your own be the stress factor; if Debby Downer seems like too much work to appease, she probably is. Keep her home.

Pack light. Don’t be the guy that keeps everyone waiting at the luggage carousel because you couldn’t not bring every color of your sweet new kicks.