Somewhere around hour six of an eleven hour flight, my client’s mother leaned across the aisle and asked the question every trip organizer dreads. Whose idea was this again? That question gets asked during nearly every family reunion abroad I have helped bring to life. Usually somewhere between booking the flights and the moment the […]

Nobody dreams about standing in a roped off line for forty-five minutes just to take the same photo three hundred people took before breakfast. Nobody books a flight, packs three generations of luggage, and coordinates six different work schedules so that everyone can spend the trip elbow to elbow with strangers, waiting their turn to […]

Somewhere between booking her mother’s plane ticket and typing “can a nine year old handle a five hour car ride” into Google at eleven at night, every woman planning a multigenerational trip to Scotland hits the same wall: Will this trip work for everyone, or will someone come home exhausted instead of happy? I think […]

A grandmother is barefoot on the bow of a small wooden boat. Her sunglasses pushed into gray hair, laughing at something her nine-year-old grandson just said. All while her daughter and son-in-law sit two feet away doing nothing but watching the coastline slide by. Nobody is checking their phone. Nobody is negotiating what happens next. […]

You have just unpacked your last suitcase from your summer vacation and someone in your family has already asked when you are going back to Cape Cod. I hear this every year, usually before the last load of beach laundry is even done. That question is exactly why I never wait until spring to start […]

The engine cuts off, and for a full ten seconds, nobody in the family says a word. There is no dock. No other boat in sight. No line of strangers waiting for the same photo they are about to take. Just water so clear you can count the fish beneath the hull. A coastline that […]

Here’s the question every parent asks me before they’ve even booked the flights: Can one island really work for a toddler who naps at noon and a teenager who wants a real adventure story to bring home? After planning enough Kauai trips to lose count, I can tell you the answer is yes, but only […]

You will not see both islands the way you picture them in your head, and the sooner you accept that, the sooner this trip stops feeling impossible. North Island vs South Island is the question every family asks me before they ask anything else about New Zealand. It’s usually somewhere around the third browser tab, […]

Most families book the wrong Greek island, and they do not find out until they are already there. The best Greek island for multigenerational family travel is not always the one with the most breathtaking photographs or the most recognizable name. It is the island that allows a child to hold a grandmother’s hand on […]

Luxury multigenerational vacations are one of the most meaningful investments you will ever make. Not in destinations. Not in departure dates. And certainly not in airline miles. They are an investment in time. Time with the people who matter most to you. Time that, if you are honest with yourself, feels shorter and more precious […]