How A Trip Comes Together: The Secret to a Great Multi-Generational Trip May Not Be What You Think
There is something incredibly special about traveling with multiple generations of your family. Watching grandparents experience a destination through the eyes of their grandchildren, celebrating milestone birthdays together, or simply sharing meals and making memories in a new place are often the moments people remember long after the trip is over.
One of my favorite trips I’ve ever planned wasn’t for a couple or even a single family. It was for 13 people spanning three generations, all traveling together to Stockholm. At first glance, it sounded like a logistical puzzle.
The grandparents wanted to soak up the history and enjoy leisurely days exploring charming neighborhoods. The parents wanted a balance of sightseeing, stellar meals, and downtime. The youngest travelers wanted playgrounds and room to run.
How A Trip Comes Together: Is the Travel Off-Season Disappearing?
Remember when the secret to saving money on travel was simple?
Wait a few weeks after summer ended, head to Europe in late September, and enjoy lower prices, thinner crowds, and that wonderful feeling of having discovered a “sweet spot” in the travel calendar.
Postcards from Canada
Looking back, I can’t imagine a better introduction to international travel with a young child. It had all the things I love about Europe: Cobblestone streets, historic architecture, cozy cafés, French being spoken all around us, Christmas markets, and storybook charm around every corner.
The best part was that we never had to deal with an overnight flight, major jet lag, or the cost of flying across the Atlantic. It also happened to be the trip that completely changed the way I pack.
Postcards from Norway
Traveling with my family is one of the greatest joys of my life. Does it come with challenges? It sure does. The truth is, family travel is rarely perfect. There are tired feet, missed expectations, weather that doesn’t cooperate, and moments when everyone needs a snack and a little extra patience. But those are also the moments that make the memories real.
Our recent trip to Norway had all of those things, and I would do it all over again in a heartbeat.
How A Trip Comes Together
Over the years, I’ve realized the parts of a trip that wear people down are rarely the actual destinations themselves. The breakdown is almost always in the transitions, whether that is the arrivals or the departures. The in-between moments are where things either flow smoothly or don’t, and it makes all the difference in whether the trip feels seamless or scattered.
Because of that, these are the things I prioritize when planning Europe trips, whether it’s a luxury itinerary or something much simpler.
Postcards from Europe: The Truth About Traveling to Europe Right Now
Every spring, the headlines about Europe start rolling in. “Tourism protests in major cities.” “New entry requirements for travelers.” “Record crowds expected this summer.”
If you only read the headlines, you might start to wonder whether Europe is becoming too crowded, too complicated, or too difficult to visit. When I start planning a European trip with clients, one of the first things I often hear is:
“Is it going to be too crowded now?”
My answer is almost always the same: only if you travel the way everyone else does.
The Way You Want It
One of the most common questions I get is: “How much did we spend last time? Almost every time, my answer is some version of: “That was a different destination. A different year. A different everything.” What you spent in 2025 on a trip to Italy has very little to do with what you’ll invest in 2026 for France. Rome is not Paris. Shoulder season isn’t peak season. Exchange rates change. Hotel rates change. Demand changes. You change. We are not talking apples to apples.
So when we discuss what you want to spend, it’s not just about numbers on a page. It’s about aligning the experience you’re envisioning with a structure that allows me to deliver it well, and sustainably.
Beyond Our Pin on the Map
I’ve always believed that travel changes us; not just our scenery, but our perspective.
Watching Pole to Pole with Will Smith beautifully reinforces that truth.
The premise is simple, yet ambitious: a journey stretching from the Arctic to Antarctica, traversing continents, climates, cultures, and communities. But what makes it compelling isn’t just the geography, it’s the reminder that the world is staggeringly vast, layered, and interconnected in ways we rarely pause to consider.
And perhaps most humbling of all? It shows us how very small our corner of it is.
The True Diamond of the Season Is Not a Debutante
Dearest Gentle Reader,
It has come to this author’s most delighted attention that the Ton has once again been captivated by the silken scandals and smoldering glances of Bridgerton. Yet while dukes may brood and debutantes may curtsy, there is one undeniable truth: the true diamond of the season is not a lady at all, but a city.
Call me biased, but as one fortunate enough to have family there and to have wandered its crescents and cobbled lanes, I assure you, it is Bath that steals every scene. With its honey-hued Georgian facades and sweeping Palladian grandeur, this UNESCO World Heritage city has stood in for Regency London across the first three seasons of Bridgerton.
Should you wish to step beyond the screen and into the world of the Ton yourself, allow me to guide you. Here are the locations no true admirer should miss.
Escorted Tours vs. Independent Travel
For many travelers, the choice between an escorted tour and independent travel feels like a fork in the road: Freedom vs. structure. Discovery vs. convenience. Adventure vs. ease.
But that comparison is outdated, and honestly, a little unfair. Today’s escorted tours look nothing like the stereotypes many of us still picture. In fact, for the modern traveler, guided travel is often not a step down from independent travel, but a thoughtful step up.
Let’s break it down.
The Secret Your Favorite Travel Influencer Won’t Tell You.
Scrolling through social media, it’s easy to think that travel is effortless. Beaches with perfect waves, hotels with pristine rooms, meals that look like art on a plate. One post and suddenly, a trip halfway around the world feels like it’s calling your name.
But here’s the secret: what you see online is rarely the full picture.
Many travel influencers don’t actually stay at the properties they highlight, or if they do, their stay is comped in exchange for promotion. Sometimes they see only part of a hotel, skip over the things that aren’t photogenic, or experience it at peak presentation for a few hours. That doesn’t make their recommendation “wrong,” but it does mean that your experience could be very different from what’s online.
Travel advisors? We pay. Just like you.
When I recommend a destination or a property, it’s because I spent my own money, slept in the bed, walked the grounds, ate the food, and genuinely enjoyed it.
One Day Your Kids Will Thank You for These Trips
Some of my most vivid childhood memories don’t come from toys, activities, or milestones at home. They come from traveling with my parents. No, I don’t remember every detail. I don’t remember where we stayed or the logistics. I remember how it felt.
Travel has a way of stripping life down to what really matters. You’re together. You’re present. You’re sharing experiences instead of screens, routines, and obligations. And those shared moments, big and small, stick.
When I was in middle and high school, I traveled through Europe with my mom, who was a multi-foreign language teacher, so languages, culture, and curiosity were always part of the experience. My mother is a first-generation immigrant, with paternal roots in Hungary and maternal roots in France. At age ten, I traveled to Le Vésinet, a suburb of Paris, to meet my aunt, uncle, and cousin for the first time. Two years later, my mother and I lived with a host family in Germany for an entire month as part of her student exchange program. During my high school years, my mother discovered she had a British half-sister living in Bath, England, and suddenly, my international family grew even larger.
Those trips didn’t just show me new places; they shaped how I see the world.
Confessions of an Introverted Travel Advisor
People are often surprised when I tell them this, so let me just put it out there:
I’m a homebody.
I love my routines. I love being home. I love not having plans. I dislike large crowds and get overstimulated with too much noise. And if given the choice between leaving the house or staying in with a cup of tea and a good book to fall into? I will almost always choose the latter.
Some of that probably comes from how I grew up. I’m from rural western Pennsylvania, where hills and muddy creeks (“cricks,” to say it correctly) run through my veins. I’m happiest when life feels grounded, familiar, and quiet.
But here’s the twist:
I also love leaving the country.
There is something about international travel that flips a switch in my brain. Different languages, different rhythms, different cultures, it energizes me in a way nothing else does. My husband knows this very well. If he so much as mentions a foreign destination, I’m already checking flight routes before he finishes the sentence.
An Insider’s Guide to Charleston, SC
Charleston is one of those places people think they know before they arrive.
They’ve seen the pastel houses, the pineapples, the perfectly staged photos taken at golden hour. And yes, Charleston is beautiful. But the real magic happens once you step just slightly off the obvious path.
So consider this your insider’s guide. The places we actually go. The meals we crave. And the spots that still make me pause, even after years of calling this place home.
Swipe, Click, Regret?
We’ve all heard the phrase “If it’s too good to be true, it probably is.” In travel, that old adage isn’t just relevant, it’s essential. With endless deals flashing across our screens, influencer-perfect itineraries, and AI-generated “dream trips” promising luxury for pennies, it’s easy to get swept up in the excitement. But travel is one of those areas where what looks incredible on the surface can unravel quickly once real life enters the picture.
AI and Travel Planning
With the rise of artificial intelligence (AI) in our world, I’m seeing writers and creatives that I follow voice their concerns, with much validity.
I’ll admit, I’ve resisted it, but finally caved and started using it to polish emails when my tone was a bit too forward. When it comes to travel, though, AI can’t replace the human touch. Not to mention all the other reasons many steer clear, like its significant drain of water and electricity, and the fact that it is replacing our critical thinking. That being said, I tested AI recently, and compared it to one of my personally curated itineraries for a client.
Magic at Europe’s Christmas Markets
My family and I recently embarked on a holiday adventure that had been on my travel wish list for years: exploring the magical Christmas markets of Europe. While I took hundreds of photos, not one of them fully captured the energy buzzing through the narrow medieval streets, the aroma of spices drifting from mulled wine stands, or the sound of laughter of families bundled against the winter chill. These markets aren’t just places you visit, they’re places you feel.

