Imagine wandering the cobblestone streets of Europe hand-in-hand with your children, celebrating life’s milestones on an African safari, or returning to a destination you traveled to as a child with your own children. Legacy travel is about more than seeing the world, it’s about passing down your values, honoring your roots, and giving your loved ones the most meaningful gift of all: time spent together.
What Is a Legacy Trip?
A legacy trip is a meaningful, intentional travel experience designed to create lasting memories and deepen family connection across multiple generations. We love supporting our clients with this type of travel because we’re not just booking a vacation we’re helping you craft a story your family will tell for years to come.
In this guide, we’ll walk you through how we plan a legacy trip with purpose and heart. You’ll also hear from our very own Brand Manager, Lindsey, who recently embarked on a meaningful journey to Scotland with her family. From the big vision to the smallest details, you’ll see how a thoughtfully designed trip becomes part of your family’s legacy.
Start With Your “Why”
The first step in planning a legacy trip (or any trip, really) is understanding the “why” behind it. This is one of the first questions we’ll ask you on your trip’s Discovery Call, too.
Ask yourself:
- What do I want my children or grandchildren to remember about this experience?
- Is there a place that holds special meaning for our family?
- What feelings do I want this trip to evoke?
Maybe you’re tracing your ancestry, celebrating a big birthday, or simply cherishing the moment before your family grows and changes.
When you’re clear on your “why,” every decision from the destination to the daily itinerary becomes more intentional. And once we understand your reason for travel, we can help you bring your dream trip to life.
Lindsey’s Thoughts:
Scotland wasn’t originally on my travel bucket list. But when my dad turned 70, he shared a long-held dream to visit the land of his ancestors and experience it together. That became the heart of our trip. And knowing my parents don’t often take big vacations made me want to get every detail just right. It’s left me, my husband and our daughter with memories that will last our lifetime. From laughing so hard watching my husband try to drive on the opposite side of the road to seeing my dad sign the ledger at Dunvegan Castle, there were so many special moments.
Design an Itinerary That Connects
Once your destination is chosen, it’s time to design an itinerary that invites connection — not chaos. A well-balanced legacy trip allows each traveler to feel seen, engaged, and relaxed.
Here’s how we approach it:
- Balance iconic with immersive: Combine must-see sights with private, behind-the-scenes experiences.
- Embrace slow travel: Fewer stops and more time in each place creates space for spontaneity and real connection.
- Weave in family rituals: A shared meal in a special setting, a nightly toast, or a travel journal can become treasured traditions.
- Include every generation: From toddlers to grandparents, we design experiences that resonate across age groups.
Lindsey’s Thoughts:
As we explored Scotland with our family, I felt firsthand how the way we travel truly transforms the experience. You can be hurried and frazzled because you’re navigating it all, or calm and cool because you know what’s ahead (like the driver that was waiting for us at baggage claim. Transfers upon arrival to a foreign country is one of my non-negotiables). We kept our itinerary engaging, but left room to breathe. One day we enjoyed a private tour of the Royal Mile, while the next was all about a slow drive to the highlands enjoying cafés and sights along the way at our own pace. We built in unhurried moments, like enjoying games after dinner or afternoon walks with gelato exploring the Gleneagles property. Everyone had something to look forward to and no one felt rushed or overwhelmed.
Add Personal Touches That Matter
What transforms a trip into a legacy? The little moments that feel entirely your own.
We love adding thoughtful touches like:
- Sweet surprises for your youngest travelers upon arrival
- A custom experience tailored to a family member’s passion like a private cooking class or art tour
- Professional photography to capture the magic
A keepsake to mark the journey – perhaps a handwritten note, heirloom gift, or custom itinerary book.
Lindsey’s Thoughts:
One thing I’ve learned, both as a traveler and now as part of Kaleigh’s team, is that when she’s behind the planning, there’s always something special in store. I’ve seen firsthand how thoughtfully she nurtures her relationships in the industry, and because of that, hotel teams and partners are eager to go the extra mile for her clients. A perfect example? My daughter has been dreaming of riding horses in Scotland, but by the time we tried to book, the rides were already full. I mentioned it to Kaleigh, and without hesitation, she picked up the phone. Thanks to her connections and the incredible team at our hotel, Evan got to live out her dream and I get to witness a moment she’ll never forget.
Let Go and Be Present
This may be the most important part. One of the greatest luxuries we offer is the ability to be fully present and not managing the logistics or juggling the schedule. With your collaboration, we can handle every detail of your trip flights, transfers, luxury accommodations, immersive experiences, family-friendly amenities, and even last-minute pivots. You simply show up and savor the time together.
After they return home many of our clients tell us, “For the first time, I was able to just enjoy the trip.” And that, to us, is the legacy we want to leave.
Lindsey’s Thoughts:
As a busy mom, I knew I wanted this trip to Scotland to be something special but the idea of researching, planning, and booking every activity for five of us felt overwhelming, especially since I’d never been before. I didn’t want to spend hours second-guessing decisions or miss out on the best experiences simply because I didn’t know what to look for. That’s where Kaleigh stepped in. Because she has been to Scotland and she knew exactly how to shape our itinerary so it felt seamless and personal. Every activity fit our family perfectly and for once, I wasn’t managing the schedule. I got to be fully present, which honestly felt like the biggest luxury of all.
If you’re ready to start planning your family’s next trip, we’d be honored to help you create something extraordinary, beautifully curated, effortlessly executed, and filled with heart.
