Group and multi-generational travel is one of my specialties, and it is also one of the trickiest things to plan well, because a great trip has to work for grandparents, parents, and kids all at once. Here is how I make it seamless.
The winners share one thing: they keep everyone together while giving each generation their own space. That usually means a private villa with room to spread out, an all-inclusive resort with something for every age, or a cruise where kids’ clubs and adult lounges coexist.
The secret is age-appropriate options each day, so the toddlers, the teens, and the grandparents are all happy, and building in both together-time and apart-time. See my family travel guide for planning by age.
For a group traveling together on one shared itinerary, I coordinate everyone under a single vacation management fee. If families have separate itineraries (different dates or plans), each carries its own. See my cost guide for details.
What makes groups genuinely hard. The villas and connected-room blocks that fit three generations get reserved close to a year out for peak weeks, everyone is flying in from different cities on schedules that all have to land within the same window, and connecting-room guarantees are often not honored until check-in unless someone has confirmed them in writing. None of it is hard when one person owns it, and all of it goes sideways when no one does, which is where I come in.
One point of contact, one plan, and a trip designed so no one feels dragged along, that is the whole job, and it is what I love most. I handle the villas, the rooms, the reservations, and the logistics, in English or Español.
The best honeymoon destinations matched to your travel style, and how to plan it right.
Read the guide →Champagne, Provence rosé, Burgundy and Bordeaux, when to go, and how it’s arranged.
Read the guide →Rioja and Ribera del Duero reds, cava near Barcelona, and sherry in the south.
Read the guide →