Coming home exhausted from a trip usually isn’t a travel problem — it’s a planning problem. We learned that the hard way more than once, which is probably why this episode hit home for us. On this one, Rita and I sit down with Paul Partridge, a former financial advisor who traded spreadsheets for travel writing, and now helps families plan multigenerational trips built around what he calls the gift of time together. His big idea is refreshingly simple: stop treating group travel like a checklist of landmarks, and start treating it like an investment in the people you’re with. Once connection becomes the actual goal, the whole itinerary changes — you start planning around shared meals, slow mornings, and enough breathing room that everyone still likes each other by the end of the trip.
One of the most useful things Paul shared is what he calls travel type matching — basically a way to keep a family reunion or a friends’ trip from turning into a low-grade turf war. He breaks travelers into four types: immersers who want deep context and museums, adventurers who need to be moving and challenged, experiencers chasing food and sensory moments, and relaxers who mostly want a good chair by the pool and to be left alone. Every group, he says, usually has all four types crammed into it, which is exactly why trying to run everyone through one identical schedule blows up. The fix isn’t control — it’s design. Give each type something to look forward to on their own, then bring everybody back together for the moments that actually matter.
Paul also flips the usual order of trip planning on its head. Most people start with “where should we go.” He starts with “who’s coming” and “why are we doing this.” A milestone birthday trip, a three-generation family vacation, and a college-buddies getaway all have completely different needs — budgets, mobility, what people actually want out of it emotionally. He also pointed out a mistake I’ve absolutely made myself: not locking down everyone’s schedule early, especially with adult kids who suddenly have their own lives and calendars (the nerve!). His fix is low-tech but effective — a simple checklist and one point person to keep things moving, while still letting the group weigh in. The goal is a trip that leaves everyone a little closer, not one where somebody’s quietly stewing by day three.
On the logistics side, Paul makes a solid case for villa or large home rentals over a pile of hotel rooms for group trips. Once you actually run the numbers — several hotel rooms versus one well-chosen villa — the value tends to surprise people, especially in the busy summer destinations. But honestly, the bigger win is the space itself: a real kitchen, shared living areas, somewhere to hide when you need five minutes alone, and natural spots where people just end up talking. He recommends going through his vetted properties with a travel concierge, so you’re not playing Russian roulette with a listing that looked great in photos and terrible in person, and arranging airport transfers ahead of time so the first hour of the trip isn’t the most stressful one.
Finally, Paul ties all of this back to something he calls “living heirlooms”. A traditional heirloom just sits in a box somewhere. A travel memory shows up every holiday when someone says, “remember when…?” He uses what he calls a five-year test to measure whether a trip was worth it — if you’re still telling the story five years later, it mattered. And the parts people actually remember are rarely the landmark itself. It’s the gelato run in the rain, the local who went out of their way to help, the laughing fit after something went completely sideways. When you plan for time together instead of just sights, you’re building the kind of wealth that keeps paying out for generations.
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