Chol Ha’moed Trip Planning – by Sarah Wikler, MA, MFT

Question: We have ka”h a large family with children of all ages. My oldest is 17 and my youngest is a newborn. Chol Hamoed trip planning has always been a source of contention for all of us. My husband and I enjoy going on trips together as a family. We feel that everyone’s schedules are so hectic during the year and Chol Hamoed provides an opportunity for the whole family to spend time together. I have such fond memories of the family trips I went on when I was a young girl and I would like to recreate those memories in my own home. Nevertheless, there is always much tension in our household when planning these trips. The older children refuse to go to “babyish” places. It is almost impossible to please everyone. This year some of my older children requested to spend the day with friends. Although they will have adequate supervision and I don’t have any other concerns, I still feel that they should be spending the day together with our family. I’m wondering if spending Chol Hamoed with friends is the proper thing to do.


Chol Hamoed is a wonderful bonding opportunity for families. Away from the distractions and hecticness of every day life, it is a chance to build memories that will last a lifetime. Many families with working parents do not have the luxury of spending time together during bein hazmanim, so Chol Hamoed may be the only family time they can enjoy.

That being said, planning an outing with children of various ages can pose great difficulty. As you correctly stated in your letter, it is almost impossible to make everyone happy. There are few options that will satisfy everyone at the same time. The stress and tension surrounding these discussions are enough to ruin a beautiful Yom Tov.

Children should be encouraged to spend time with their family. Following are some suggestions that can help to ease the tension:

I know a family with two children, a girl and a boy, who are four years apart in age. Their parents very much wanted to avoid the ‘Chol Hamoed trip-planning stress’ so they devised the following plan: They told their children that they would each get one day of Chol Hamoed to plan the outing for that day. Both children would participate in both outings, but the one to whom the day was assigned chose the destination.

This idea can be adapted by your family according to your personal preferences, taking into account the ages and genders of the children in your family. For example, you can designate the first day of Chol Hamoed as ‘boys’ day’, and the boys get to choose the destination for that day. The second day of Chol Hamoed could be ‘girls’ day’, and the girls get to choose the destination. Alternatively, you can decide that the first day your teenagers or older children can plan the trip, and the second day the younger children can choose a trip that they would enjoy.

Another option would be to plan a two part trip. Children often feel pressured to plan an all-day ‘amazing’ trip because the entire day will be committed to that one activity or destination. And what if it turns out to be boring or juvenile? But if they know they will be doing something else later that day that will be enjoyable (at low-cost or no-cost), even if it’s for a shorter period of time, they are more likely to agree on the primary destination and be happy to participate in the trip. Arranging two smaller trips, or one big one and one small one, can make more family members happy.

My last suggestion is to combine both options. Each day would have one main trip and one smaller trip/activity. On the boys’ day, the boys get to choose the main trip and the girls choose the smaller trip, and on the girls’ day the girls get to choose the main trip and the boys choose the smaller trip. This way everyone is doing something they enjoy each day.

What do you do if there are three days of Chol Hamoed? Who gets the third day? There is no a chiyuv to go on a trip every single day of Chol Hamoed, but if you wish to, there are a couple of options. Day three could be ‘parents’ day’, and they may opt to allocate that day to Mommy so that she can prepare for the second days of Yom Tov (and the children may help her or join their friends that day.) Or the parents may opt to go on a one or two part trip that day.

And if there are four days of Chol Hamoed? The fourth day could be a family-centric trip, such as going to visit Bubby and Zeidy in Brooklyn. Once the children have had the trips of their choosing, they will not resent spending a day of Chol Hamoed visiting Bubby and Zeidy.

All of the above should be discussed with your children before Succos begins. It’s not a good idea to wait until the morning of the first day of Chol Hamoed to broach the topic. If negotiations for that day’s destination have not even begun yet, the family is already off to a late start and it is very likely that no one will want that day as their day. Make sure to explain why you’re proposing this approach; you want to make this a shared family time, pleasing everyone yet considering that they each have different interests.

With a little thought and planning, disappointments can be avoided, and Chol Hamoed can be both stress-free and enjoyable. Have a wonderful Yom Tov!

Sarah Wikler, MA, MFT, a former high school principal, is a therapist in full-time private practice in Lakewood, N.J. She works with children, teenagers and adults, specializing in treating anxiety, depression and trauma. 

Reprinted from the Lakewood Shopper.

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