One of my favorite vacations was a trip I planned for a multi-generational family in Tuscany. I had planned the parent’s honeymoon, and then their three children’s honeymoons and now I was planning their first trip as an extended family group with their first two grandchildren—ages 1 and 5.

We agreed that renting a villa with a pool would be the best way for them to be together as a family. I found a villa with seven rooms and a lovely pool looking out at the Tuscan hills. It was perfect because everyone had their privacy, yet there was plenty of living space for the family to gather.

I arranged for them to be met at the airport so they would not have to get off a plane and then navigate to the villa on their own. They had a car at their disposal, but we did not want anyone to be the designated driver on the days they did wine tastings or deal with the traffic of Florence, so we hired a car and driver on those days.

The villa made meals arrangements easy and gave them a sense of everyday village life. They picked up groceries in little towns with the caregiver from the villa; plus I gave them a list of farmer’s markets that they could stop at as part of their daily outings.

Their days had a comfortable rhythm. Everyone gathered for breakfast each morning. Most days, they ate lunch out as part of their day’s activities, and generally, they dined in together or went to a nearby restaurant in the evenings. It was easy and stress-free and we brought in a chef for the nights they wanted to eat in.

The villa was centrally situated. Most places they visited were within an hour’s drive. That meant they could do a different day trip or activity each day and still return by 3 or 4 p.m. so the kids could jump in the pool. The kids went with the flow; we had a babysitter on tap, although I think they only used her once.

I had fun giving them options of all the wonderful things in Tuscany I loved. For example, they took my favorite cooking class, went to a pig farm, and went to Siena and learned about the Palio, an ancient horse race where neighborhoods compete against each other. They also explored medieval towns such as Montalcino and Montepulciano and did several wine tastings.

Back home, everyone thanked me for the amazing trip. They said villa had worked out wonderfully and they loved the activities I’d set up. Most of all, they said they loved the fact that they were all together on vacation as a family.