Navigating Spring Break with My Family

Photo Credit: Etan Horowitz

Were I a tour operator trying to recruit grandparents such as myself to splurge on trips for grown children and grandchildren, I’d use a brochure showing little ones licking ice cream cones and sporting big smiles. Creating happy memories would be the name of the game. Not shown would be even a whiff of bickering or normal sibling rivalry. 

My own reality is a bit different. I think we began taking one nice vacation a year when my grandson, Jack, was five and my granddaughter, Lucy was two. We traveled to resorts in Maui and Kaua’i for the children’s spring breaks. We also traveled to a beautiful Club Med in Ixtapa, Mexico and an okay Club Med in Cancun.

Last April marked our last spring break in Mexico. This featured a stay at Planet Hollywood, Cancun, where my grandchildren and their parents had a good time. My memory of that trip is a nightmare, because I was plagued by an illness featuring diarrhea and vomiting. After four days in bed, I announced that spring break 2026 would be in Italy. 

By chance, Etan had spent a week in Italy for work before joining us on the Planet Hollywood trip. As I could have predicted from two of my prior trips, one to Rome and one to Venice, Rome, and Florence, he loved Italy. When Daphne saw the beautiful leather goods he brought home, she came on board too.

Etan is a genius at logistics when he has the time. He knows the best places to eat, the coolest activities, and the best places to shop. Daphne has little interest in trip planning. When I text her my thoughts for places to eat or visit, she typically responds: “Mom, start a Google doc.” 

So I've proposed that we have a family meeting when I visit the kids at their home outside Philly in a few weeks. I hope that Jack, now 14 and Lucy 11, will tear themselves away from their electronics long enough to take part in the discussion.

Here’s where it becomes challenging. Daphne expressed an interest in visiting Venice, and Etan thought he and the children might too. Assuming we’re also going to Rome and Florence, that’s a pretty packed itinerary for the 7 nights they can spend in Italy without the grandkids missing school. Also, my tolerance for taking high speed train trips lasting more than two hours is limited. Is it selfish for me to suggest that those interested in visiting Venice do a day trip from Rome via high speed train?

While I prefer hotels featuring sumptuous breakfast buffets, Etan tells me that Airbnb rentals are likely to be more centrally located, and will allow for four bedrooms and two bathrooms. I’m willing to cede his points even though I worry Airbnb’s can be quirky.

 Does that leave us with an itinerary that will elicit great big smiles from everybody? My thinking may evolve, but if I’m the only one with a big interest in returning to Florence, I should fly there and stay two or three nights at a nice hotel before taking a high speed train to Rome for seven nights at an Airbnb with the family. That will afford me the opportunity to appreciate the ultimate in Renaissance art, stroll along the Ponte Vecchio, and get to the leather market where I’m hellbent on purchasing a custom-tailored jacket.

Granted, Jack and Lucy have very different interests, and can get testy when their differing wishes fail to be granted. Jack might enjoy a walk with an expert photographer, and Lucy a class in how to make gelato. As a grandmother, I get that the parents have final say.

So I’m looking forward to making memories with photos depicting my family eating delicious meals, and licking gelato cones in front of the most beautiful fountains imaginable. Do you foresee any wrinkles?