Vacationing in Large Groups

Make sure the smiles are for real!

This summer my family is having a reunion at the same Northern-Wisconsin resort my parents owned in the 70’s and 80’s. Hats-off to my mom who is organizing the trip for 16 to 18 people. Heck, organizing a weekend getaway for my family 4 (5 with the dog) is nearly impossible.

Do you have what it takes to organize a large group?

Don’t go into the leadership role halfway; reluctant leadership is worse than none at all. Remember, the best leaders actively delegate.

Avoid looking back on your trip and saying, “we should have done some group psychological testing before the trip.” I know, it’s not practical to ask my two sisters, (I mean) everyone you’re considering traveling with to submit to testing (no matter how tempting the idea is). But, if your group came together by happenstance; the Leader should ask questions. There are no “right” or “wrong” answers; their greatest value is self-awareness.

General Attitudes
The passive/aggressive is the achilles heel of any travel group. They will not state their needs up front, but they will openly complain during and after the fact if their needs are not met. Avoid them at all costs! Get answers…How much time do you want/expect to spend with the group? How much alone? What travel pace do you prefer?

Differing attitudes about money is one of the key factors leading to divorce. If $ can split up people who plan to spend their lives together, imagine what it can do to those who’ve only committed to 7 days of togetherness. Ask about equally handling big expenses (example, damages to rental property) which we know would never really happen.

Do everything you can to enjoy your vacation and, if you have accepted the role of Leader, part of your job is to help your entire group SMILE.

We want to help you explore Wisconsin, visit

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