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The Gift of Time Together

Podcast: Wherever We May Roam — Travels With Jim and Rita  Hosts: Jim Santos and Rita Santos  Release Date: September 9, 2026 Listen on: Apple Podcasts Full Episode Transcript: [00:00] Jim Santos: Have you ever returned from a trip feeling completely worn out? Well, maybe we can help. Today we’re talking to someone who can […]

Italy, Italy, & More Italy With Multi-Generational Travel Planner, Paul Partridge

Podcast: Where Have You Been? — Travel Stories  Host: Bill Roehm (William Roehm)  Release date: August 16, 2026  Listen on: Apple Podcasts Full Episode Transcript: [00:00:00] Paul Partridge: Evidently, I wasn’t accelerating fast enough because she like zoomed up, kind of like, right up behind my tail then zipped around really fast. And as she […]

How to Plan a Family Vacation: 8 Decisions That Shape Your Trip

How to plan a family vacation

When you’re thinking about how to plan a family vacation, picture a moment you’d like everyone to share. Perhaps it’s a birthday dinner with three generations around the table. A morning when cousins who live far apart finally have time to play. Or a conversation that carries on long after the plates are cleared. Those […]

How to Turn a Multigenerational Trip Into a Family Heirloom

Mother and daughters enjoying an afternoon cruise during a multigenerational family vacation.

Discover how thoughtful planning, shared experiences, and time together can create memories your family will treasure for generations. What will your family inherit from you? Perhaps a watch, a piece of jewelry, or a collection of photographs carefully preserved and passed from one generation to the next. But some of the most meaningful things we […]

How to Plan a Multigenerational Vacation Everyone Will Remember

Young woman bottle-feeding a sheep at a working irish farm during a multigenerational vacation.

You can plan every detail of a once-in-a-lifetime family trip and still come home thinking, we barely connected. The flights were booked and the dinners reserved. The itinerary held everything you were told you couldn’t miss. But somewhere between the tours and the transfers, no one had a chance to slow down. The organizer spent […]

How to Organize a Group Trip and Still Enjoy the Vacation

Group of friends on a friends' trip pause on a hiking trail to take photos of the pacific ocean.

Nearly every family or group of friends has one: the person who starts the group chat, researches the destinations, compares the rentals, tracks everyone’s dates and remembers who can’t eat what. Then the trip begins, and everyone else goes on vacation while that person becomes the transportation coordinator, restaurant manager and answer desk. Where’s the […]

How to Plan a Family Trip That Brings Everyone Closer

Two women stand in turquoise water in front of a pink waterfront villa in turks and caicos.

You can spend a fortune on a once-in-a-lifetime family vacation and still come home thinking, we barely connected. Maybe the rooms were scattered across different floors. The adventurers headed off to hike. The relaxers slept in. The grandparents needed a slower pace while the teenagers wanted something more exciting. And the only time everyone was […]

Read This Before You Hire a Travel Advisor

Family and friends gather around an outdoor dining table at a modern greek villa.

Have you ever been to a really great restaurant? Before they hand you the menu, before they mention the specials, before they even take your drink order — they ask if anyone has allergies. Why? Because that answer shapes everything that comes next. Travel planning works the same way. Most advisors plan the way the […]

Why the Best Trips Aren’t Perfect

A tranquil scene of fishing boats docked in front of colorful buildings in prince edward island, canada.

There’s a moment that happens on almost every trip. Something small goes wrong. A meal doesn’t live up to expectations. The air conditioning is underpowered. A plan runs late. A detail slips. In the moment, it’s frustrating. But here’s what’s interesting: When people look back on their favorite trips… those moments almost never matter. The […]

What Mikhail Gorbachev and Bruce Springsteen Taught Me About Villas

Multi-generational family lounging at the edge of an italian villa pool with panoramic countryside views, celebrating a family reunion

“Please,” said the general manager. “We ask all guests staying in the penthouse to sign the guest book.” “Of course,” I said, accepting his Montblanc pen with feigned nonchalance — as if I did this every day. The year is 2002. My wife and I and two young daughters are in Italy, checking into one […]

Get The Together Letter

Ideas for turning “we should all get together” into a trip everyone still talks about for years.