Thursday, November 1, 2007

Going with the Gang: Deciding when and where

You don’t need a marketing study to know that one of the hottest travel trends of the last few years is vacationing with friends and family. Traveling together builds bonds and memories and offers a concentrated “time out’’ from an insanely busy world.

With weddings, guests have it easy. The bride and groom set the agenda; the only negotiating is between them (and possibly, their parents.) As a guest, you need only attend – or not.

But putting other trips together can be like herding cats. Add in the family emotions that sometimes lurk beneath the surface (“Mother always loved you best’’) and your hug fest can turn ugly.

Borrowing from personal experience (I’ve arranged trips for family, friends, couples and yes, even business conferences) and those of others I know, here’s a cheat sheet on planning a group trip. It might not seem like the quick-and-easy way to do this, but it’s the best we’ve found. (See time-saver tips below. And if you’ve got better ideas, or experiences to share, just Click to Comment below. You don’t have to register.)

  • Choose a group leader. Yes, you need one. This is the person who gets things rolling and keeps the plan moving. But -- you don’t want the kind of leader who takes over entirely and plans the trip only he/she wants.

    (Having that problem? Direct your group leader to this posting and make up some excuse about seeing some other tip.)

    One solution: If it’s a similar-regular event, like a family reunion, rotate planning responsibilities. This keeps one person from taking over – and shares the hassles.

    One immutable rule: The group leader must be discreet. If Susie insists she isn’t coming if Anna comes, that’s Susie’s business. The leader absolutely positively shouldn’t share this with others.
  • Be clear about the group leader’s role. Who wants to be a babysitter? A smart group leader states at the beginning, “My job is to facilitate getting us all on the same page. I am not responsible for booking your arrangements or taking care of your personal problems once we’re on the trip.’’

  • Ask, "Why are you doing this?" Sounds obvious. But as my colleague Marjie Lambert learned, not everyone is signing up with the same goal in mind.

    So ask yourself (and members of the gang):

    • Is the trip mostly about reconnecting? If so, make that clear. Politely remind people that while you’d like the location to be comfortable for everyone, that’s secondary. (It helps put the gang in a give-and-take frame of mind.)
    • Or is the point to visit a particular place? Sure, you’d like to see it with people you like. But if you’re going to this place with or without them, then don’t expect everyone on your list to go. Some people won’t have the time, money, interest.

  • Decide on the group. If you’re footing the bill, it’s nobody else’s business who’s on the list -- and I’m not 100 percent sure it’s their business even if it’s a Dutch-treat invitation. Still, you can’t blame someone for wanting to know with whom they’ll spend the weekend/week …especially if it’s going to cost them money.

    (The exception to this is a wedding. The bride and groom’s wishes trump all, and you should not ask who else is coming before you decide to accept. But yes, it’s O.K. to politely inquire after you’ve RSVPed.)

    Unless everyone already knows who else is invited – say, all your old college suitemates -- the leader may, again, want to be discreet. Sometimes, if one person isn’t coming, the group may decide to add another person. You don’t want him/her feeling like a substitute.

  • Choose the date well in advance. For groups of more than 4 or 6, at least a year is recommended. (One of my three siblings is retired, and it’s still a nightmare getting us all to agree on a date!)

  • Agree on a budget. Even when you’re traveling with family, you might not really know what they can – or are willing – to afford. And there’s nothing worse that being in the “I can’t afford it’’ position.

    Here’s one strategy: The group leader sends out an e-mail with various options; everyone replies by secret ballot. (Yes, if you use e-mail, the group leader will know. Another case for discretion.) The options might range from “Here are three hotel prices. Which suits you best?” to “Here are three tours. Let me know if there are any you like best, and any you just aren’t interested in at all.”

  • Narrow locations. I’ve seen three approaches work.

    • The group leader picks. Everyone else comes – or doesn’t.
    • Everyone votes. The group leader solicits nominations by e-mail. He/she puts them out for discussion (see Time-Saver Tip, below) and, on a certain date, calls for binding vote.
    • Pull it out of a hat. A group of friends in Miami each put their top choice into a bowl, agreeing to all abide by the random-draw choice. The winner was Marrakesh. And yes, they came back friends.

  • Now, here’s a biggie: If someone turns you down, don’t take it personally.

      That’s stickier than it sounds. Earlier this year, I started planning for a Significant Birthday – an African Safari. I followed all the rules: started a year out, asked people what price range suited them most (since my picking up the tab is completely out of the question.)

      Pretty much everyone decided not to go, and I have to admit, I felt a bit hurt. After all, I’d only invited my closest friends; didn’t they understand that?

      Then another group of friends started planning a Baltic cruise, and I realized how my birthday guests felt.

      We love the people involved, like the idea of cruising the Baltic. And while we’ve tentatively signed up, we’re on the fence. Money and time are big factors – but so is the ship that’s been chosen.

      I knew in advance what ships were under consideration and tried gently to nudge in the preferred direction. (One ship was much smaller than the other, and that factor is important to us. Price was the same.) But I didn’t want to be churlish, and so I resisted the direct approach of “We’re most likely to go if Ship B is the choice.’’

      Of course, Ship A was chosen.

      If time and money allow, we’ll probably still go. And we’ll have a great time. Because anybody who goes on a trip with any other attitude shouldn’t go at all.


      Set up a wiki. (That’s a website that all the members of your group can easily access and post on.) This enables the group leader to put the itinerary in one place that everyone can reference. The group can make lists and assignments (who will bring what, which couple is researching which port).

      Best bet is Triphub , set up just for groups traveling together. It’s website offers a wealth of help and let’s travelers set up their own group page (for free, of course.)

      Other sites that let you easily set up a free wiki are Pbwiki, Wetpaint and Wikispaces.


    • and Orbitz both allow for group bookings.
    • Travelocity has a “meet me in…’’ tool that helps you plan a trip with a friend who lives in a different city. Look under “Last minute packages.’’
    • Not the most sophisticated site, but it has some useful tips.
    • Group Travel Directory is a listing of group travel suppliers. Though it is aimed at professionals, you may find some good ideas here.


    • Cruises. Tons of flexibility for all ages. (Word to the wise: Check shipboard activities; On some ships, older teens and young adults can find themselves bored.)
    • Rented house/condo (or a group of them). Beach, mountains, lakes and islands are all good choices; so are foreign destinations like Italy.
    • Theme park. There’s a reason these are so popular. (Even an anti theme-parker can have fun if they just give up the grouch.)
    • Urban scenes. Cities like New York, Chicago, New Orleans, Portland and Las Vegas are good options if everyone in your group is mobile. Be sure you pick a place where you can get around easily via foot and public transport.
    • Festivals/events: Food fests, fringe theater and other arts festivals can be great – as long as everyone in the group shares a love of the activity.


    Before you opt for one person’s house or home turf. All kinds of power plays and resentments can come into play. (These reunions work only if the host/hostess is super-relaxed and everyone pitches in.)

    NEXT WEEK: Creating an itinerary.


    PHOTO: For a recent Wooldridge sibling reunion, we opted for Santa Fe ... mid-way between all our homes, with enough to do for a long weekend.
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