Thanksgiving is almost here, and every year around this time I start looking back on the trips I’m grateful for, both my own and the ones our clients took. This year, a note from one of our clients is at the top of that list.
One of our clients had just returned from a trip with his family, one he very nearly sat out. Work was pressing, and the timing felt wrong. For a while, it looked like he would stay behind. In the end, he went.
A few days after he got home, he sent me an article about how we rarely regret the trips we take, only the ones we don’t. He added a little note saying how glad he was that he’d decided to go.
I read it twice and wrote him back that same afternoon. He had put words to something I’ve felt for years, first as someone who loves to travel, and as someone who gets to see firsthand what travel experiences mean to the people who trust me to plan them.
I have never regretted a single trip. Not the long flights, not the ones that cost more than I planned, and not the ones I nearly talked myself out of. Who are we kidding…there are none of those!
That’s the heart of meaningful travel. It stretches you in the best way, through a language you don’t speak, a history you didn’t know, or a story told by someone who lived it. There is never a perfect time to go, and the world keeps changing while we wait. The trips we take become the stories we’re most grateful for.
When I count what I’m thankful for this year, a surprising amount of that list began somewhere I couldn’t read the menu.
There Is Never a Perfect Time
There will always be a reason to wait. Work gets busy and the calendar never seems to open up, and someday is a very comfortable place to live.
The trouble is that the people who make a place special won’t be there forever. The grandmother teaching cooking classes in her village kitchen will hang up her apron one day, and the guide with the stories everyone remembers eventually retires. Closer to home, the kids at the table this year will be setting their own tables before you know it, and you won’t always have every generation of your family healthy and able to go.
Our client almost learned that the hard way. Instead, he came home with a family trip he’ll talk about for the rest of his life, and he’s already planning the next one.
A Lesson From the Ballet Studio
My daughter, Bailey, grew up studying ballet with a teacher who had one phrase for every nerve-wracking moment: get comfortable being uncomfortable.
He said it before competitions, when she stood alone before a panel of judges, and again in the wings, right before she walked onstage to a packed auditorium. To him, the nerves signaled she was doing something worth doing. I sat in on enough classes and watched from the wings enough times that his phrase became mine.
The trips I love come with every comfort, and they put me in moments where I have to stretch, like ordering in a language I don’t speak or tasting something for the first time. That’s how I’ve learned that my way of doing things is only one way.
The travel I love isn’t uncomfortable. But it does put me in moments where I have to stretch. Not speaking the language. Trying something I’ve never tasted. Seeing life through completely different cultural glasses, and realizing my way of doing things is only one way.
That flutter you feel before saying yes to a big trip is the same one Bailey felt backstage. It usually means you’re about to do something you’ll be grateful for.
The Moments That Change Us
My favorite travel memories come from sitting with someone and asking about their life. Those are the moments we plan for, and the ones our clients thank us for years later.
In Lisbon, it might be a small fado house in the Alfama after dinner. The lights go down, and a singer fills the room with a longing you feel before you understand a single word. If you’re lucky, she’ll stay afterward to tell you about saudade, the Portuguese word for missing something you love. You come home with a word you didn’t have before, and you find yourself reaching for it.
On a Greek island, it might be an afternoon in someone’s kitchen. A grandmother rolls out dough for pites and insists you eat far more than you can. She’ll tell you about philoxenia, the ancient Greek belief that a stranger at your door is a guest. Those of us raised on Southern hospitality recognize it right away. You leave with a recipe scribbled on the back of something, and a higher standard for how you welcome people into your own home.
In Berlin, it might be walking along what remains of the Wall with a guide who grew up on its eastern side. She describes the November night in 1989 when the border opened, and history stops being a chapter in a textbook. You come home reading the news differently, with more patience for how long it takes a place to heal.
In Japan, it might be a night at a temple on Koyasan, the mountain home of Shingon Buddhism. Dinner is shojin ryori, the monks’ vegetarian cuisine, served on lacquer trays. Before dawn, you’re invited to morning prayers amid the chanting and incense of a faith that may not be yours. Some of that stillness follows you home. (If food is your way into a culture, our Japan food guide is a lovely place to start.)
In Zambia, it might be the evening your guide sits with you by the fire and talks about the village he grew up in and what the bush meant to him as a boy. You came for the elephants. You come home talking about him, and the children in the village. (More on what safari is really like in African Safari Misconceptions, From Someone Who’s Been.)
How We Plan for Moments Like These
Moments like these come from people, and that’s where most of our planning energy goes, into finding guides who are natural storytellers and families who will set another place at the table. At Le Bèrne in Montepulciano, our clients meet three generations of one winemaking family, including a grandfather in his eighties who still drives the tractor. Those introductions are built over years, and they’re what I’m proudest to share.
We also plan for curiosity. If you tell me you’d love to cook in Tuscany, I’ll ask whether you want a chef who speaks English or a nonna who doesn’t. Those are very different afternoons, and each one is wonderful for the right person.
Pacing matters just as much. We leave room in the day so that when someone invites you to stay for one more glass, you can say yes. The property waiting for you that evening should be a place you’re glad to come back to.
For families, the work becomes even more personal. A grandfather and a fourteen-year-old will be moved by very different things, and so will the mom who hasn’t had a full night’s sleep since spring. We design for every one of them, and we make sure everyone ends up at the same table for dinner.
Most reasons people wait come down to the planning itself, the hours it takes and the worry about getting it wrong. That part is ours, and all that’s left for you is the yes.
The Trips We Almost Didn’t Take
It’s crazy to think how close our client came to staying home. So many of the stories I treasure most come from trips that almost didn’t happen. The inbox was full, and there was always a reason to wait until next year. Every time, I came home grateful I went.
In my reply, I told him that travel has made me kinder and more curious than I was before, and I believe that with all my heart. I see it in small ways at home. Some evenings we pour a sundowner on the porch, a habit we brought back from Africa, and sit outside just to watch the light go. When our family gathers this Thanksgiving, I already know which stories will come out between the turkey and the pie, and every one of them started with a yes that wasn’t always easy.
I closed my note by telling him I hope we get to be uncomfortable together one day, in Africa, Japan, Peru, or somewhere neither of us has imagined yet. Just tell me where.
I’d say the same to you.
I plan to leave this world with a full heart, an open mind, and a lifetime of stories I’m grateful I said yes to. If 2027 is the year you stop waiting for the perfect time, I’d love to hear what you have in mind. Inquire here, and we’ll schedule a private appointment by phone or video.
Five Questions for Dianna
Q1. Are people waiting for a better time to travel, or for permission to put themselves and their families first?
Time and money are the two reasons I hear most often, and they’re real reasons. Even so, I’ve watched people find room for both once a trip becomes a priority. Often what they’re waiting for is permission to put their family first, and I’m always happy to give it.
The planning itself holds people back too, and that’s the part I can take off their plate entirely.
Q2. Bailey’s ballet teacher used to say, “Get comfortable being uncomfortable.” When did that advice come back to you on a trip?
Africa was a trip I’d wanted to take for years, and I was sure no part of it would make me nervous. Then we went out on the Zambezi River from Lolebezi Camp in Zambia, and it turns out I’m pretty terrified of hippos.
There were hippos everywhere, and uncomfortable didn’t begin to cover it. What made the difference was our guide. He knew those animals and how they behave, and he had a deep respect for the river they live in. I trusted him, even though I’d have been perfectly happy to turn that boat around.
If I’d insisted on going back, I would have missed the sun going down over the Zambezi, one of the most beautiful sunsets I’ve ever seen. Sometimes getting comfortable being uncomfortable just means trusting someone who knows a whole lot more than you do.
Q3. Is there a difference between what clients expect to be the highlight of a trip and what they talk about when they come home?
Everyone comes home with different favorite moments, and I love hearing which experiences made the biggest impression. But what makes me proudest is how often clients tell me how much they simply enjoyed being together.
With Mer Bleue, you can experience everything you’ve been looking forward to without spending your time figuring out how to make it all happen. You won’t worry about transportation, directions, reservations, or what comes next. We’ve already taken care of all of that. Instead, you get to be fully present, enjoying the destination and, more importantly, the people you’re sharing it with.
The greatest luxury is having absolutely nothing to manage and being able to enjoy every minute together.
Q4. Does every trip need to be transformative?
Not at all. Some of the trips that mean the most are the simplest.
Three days at a beautiful beach hotel with your favorite person can be exactly what you needed. You come home rested and a little closer, and that counts.
I think we sometimes get too caught up in what makes a trip impressive rather than what makes it worthwhile. What makes travel special isn’t necessarily where you go, how much you spend, or how extraordinary the experiences are. It’s whether the trip gives you what you were hoping for, or perhaps something you didn’t even realize you needed. And that’s going to look different for everyone.
Q5. Looking back on trips with your own children when they were young, is there one you’re especially grateful for now that they’re adults?
Our first family trip to Europe. The kids were in first and second grade, and we spent an entire year getting ready for Italy, Greece, and France. I found little ways all year to introduce them to the places we’d visit and the things we’d see. They saved their own spending money, which we exchanged for euros, and each of them had a camera and a journal to document the trip.
We’d never been to Europe either, so we were seeing everything right alongside them. We didn’t know what we didn’t know, and that made it all the more exciting.
What I love most is that the trip kept meaning something long after we got home. Years later, the kids would come home from school saying, “Mom, we were there. We saw that!” I didn’t realize then how much those trips would shape the way they understand the world, and now that they’re grown, I’m awfully grateful we had that time together.
