Coming to Israel for the Chagim? Don’t Leave Chol Hamoed to Chance

Every summer, my WhatsApp starts pinging with families planning their Sukkot in Israel.

One conversation this week made me smile.

Let's call her Miri.

Miri is a busy grandmother whose happiest weeks of the year are spent in Israel surrounded by her children and grandchildren. They've been doing this for years, and by now they've got the logistics down to a fine art.

The apartment has been booked months in advance. The Yom Tov meals are planned. Everyone knows where they're sleeping. On paper, everything is organized.

"So," she said to me, "what are we going to do this year?"

It's a question I hear surprisingly often.

The challenge isn't finding something to do in Israel. The challenge is finding something that works for everyone. The grandchildren range from toddlers to teenagers.

Some family members haven't visited Israel for years and want to see every historical site they can fit into the trip.

Others were here last year... and the year before... and the year before that. The thought of another visit to the same attractions doesn't exactly fill them with excitement.

Some people are looking for adventure.

Others just want a relaxing day together.

Grandma wants everyone to enjoy themselves without feeling she's organizing a military operation.

That's where the fun begins.

Instead of trying to make everyone do the same thing, we started building a day around the family.

So on a typical chol hamo'ed day, the youngest grandchildren spent the morning with Grandma at a shady park, feeding animals in a petting zoo and enjoying the playground.

Meanwhile, the older cousins disappeared for an exhilarating ATV adventure that left them covered in dust and wearing enormous smiles.

Later, everyone reunited in the park. Some kicked a soccer ball around, others found a quiet corner to chat, and the younger children proudly showed off the goats they had fed that morning.

By evening, the whole family was back together, sharing dinner in the sukkah of a local winery, laughing about their completely different days while enjoying the same meal.

Everyone had done what suited them best, but they'd still spent the day together.

Another year, the answer might be completely different.

Perhaps one branch of the family wants to explore underground caves while another spends the afternoon making chocolate.

Perhaps the adventurous teenagers head off for scuba diving while younger siblings enjoy a creative workshop.

Sometimes it's a guided tour through a neighborhood that several family members have never experienced. Sometimes it's an activity that most tourists; and quite a few Israelis, have never even heard of.

Over the years, I've collected an ever-growing collection of ideas.

Not (only) because I search the internet for unusual attractions.

Because families come back and tell me, "That was the highlight of our trip."

Or I visit somewhere myself and immediately think, "One day, the right family is going to love this."

Those ideas stay with me until the perfect opportunity comes along.

No two families are the same, so no two Sukkot itineraries should be the same either.

Some families need downtime.

Some need excitement.

Some need history.

Some just want to make sure that the grandparents aren't left entertaining energetic grandchildren while everyone else disappears for the day.

The greatest compliment I receive isn't when someone tells me they loved a particular activity. It's when they tell me, "Everything worked."

Nobody spent hours wondering what to do.

Nobody argued over where to go.

Nobody came home exhausted from trying to please everyone.

They simply enjoyed being together.

After all, that's why they came to Israel in the first place.

If you're planning an Israel trip and want help deciding where to invest your time, your budget and your energy, I'd love to help you create an itinerary that's right for your family. You can reach out via my contact form

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