Distinctive travel,
thoughtfully
designed.
Highly personalized trips for families, couples, and groups — blending luxury, character, and a genuine sense of discovery. Every journey is built around you.
Travel, designed
around you
I create tailored travel experiences that balance discovery with ease. The goal isn’t the obvious trip — it’s the right one. Whether that’s a family-friendly beach escape with real character, a multi-generational adventure, or an unhurried week in wine country, every journey is thoughtfully designed from start to finish.
Families
From beach resorts to European summers to multi-generational adventures — memorable, well-paced trips for families at every stage.
Couples & Milestones
Honeymoons, anniversaries, babymoons, and landmark birthdays. A trip that feels like it was made for the moment.
Groups & Friends
Golf itineraries, friends trips, and curated group escapes. One point of contact, every detail handled.
Most people can find a hotel.
The challenge is finding the right one.
“Sailors navigated by the Southern Cross when venturing beyond the known world. Mountaineers follow cairns — piles of stones stacked to mark the trail — when the path gets unclear. I’ve spent my career learning this terrain. I’m here to guide the way.”
Global Network
Years inside the hospitality industry means I understand what makes a hotel exceptional — and what the brochure doesn’t tell you. You benefit from that knowledge on every booking.
Preferred perks
As a Virtuoso-affiliated advisor, I secure complimentary upgrades, resort credits, and amenities not typically included with standard bookings. You benefit from added value and a more seamless experience.
One trusted contact
From initial conversation to the moment you check out, one person who knows your trip inside out and can handle anything that comes up.
Typically no cost
My services are typically included as part of your booking. I work with a network of trusted travel partners to enhance your experience with additional benefits and support along the way.
However you like to travel,
I can help.
End-to-end trip planning
Start from scratch or a vague idea. I handle everything — destination, hotels, flights, activities, and itinerary — from first conversation to final booking.
Book a trip you’ve planned
You know where you’re going. I secure preferred amenities, added value, and handle all the logistics — often enhancing what you’d receive booking on your own.
Travel Rewards Guidance
Make better use of the travel rewards you already have. I’ll help you understand your options and apply them to your trip in a way that’s simple and effective.
Travel consultation
A focused advisory session for travelers who want expert input on a trip they’re planning themselves — recommendations, itinerary structure, and insider guidance.
In most cases, my services are included as part of your trip. I work with trusted travel partners who compensate me directly. For more specialized support, such as consultations or rewards guidance, a separate fee may apply, which I’ll always discuss upfront.
The destinations I’d
plan for you today
These aren’t destinations I’ve read about. They’re places I’ve been, stayed, eaten, hiked, and explored — and know well enough to plan properly. Hover to learn more about each.
consulting
points earned
The perspective behind the trips
The best trips aren’t always the most obvious ones, but should always feel right for you.
I’ve been traveling my entire life, starting with family road trips across the U.S., summer vacations on Cape Cod, and more Disney World visits than I can count. Those early experiences shaped my appreciation for what well-planned travel can be.
That instinct deepened as my travels expanded. Studying abroad in Rome and New Zealand meant not only navigating a tight budget, but also learning how to find those hidden gems just off the beaten path. In the years since, I’ve traveled to more than 40 countries, refining that same approach across a wide range of destinations and experiences.
Of course, my tastes have changed and the experiences have become more elevated. Now the perfect itinerary includes finding the perfect vineyard in the Loire Valley, enjoying an experimental tasting menu at a World’s Best restaurant in Santiago, or cozying up by the fire at a boutique bed and breakfast in the Cotswolds. There is nothing like discovering that distinctive and thoughtful travel experience that’s just a bit outside the ordinary.
Perhaps it’s no surprise, then, that over time I have become the person friends and family turned to when it comes time to plan a trip: someone who instinctively knew where to go, where to stay, and how to bring the pieces together in a way that felt seamless and well considered.
My career followed that same instinct. I began in consulting, traveling extensively across the U.S., and later spent years working in the hotel industry, developing a deep understanding of what separates a good stay from a truly exceptional one — knowledge I now bring to every client trip.
Today, travel is both personal and constant. I travel with my wife, with friends on golf trips, and most importantly with our three young children. Those experiences shape how I design trips, balancing uniqueness with ease, and ensuring that every detail works for the people actually taking the journey.
I founded Crux & Cairn to help people find the perfect trip for them, whether that’s a classic destination done exceptionally well or something a bit less expected, always with the goal of creating travel that feels thoughtful, seamless, and genuinely memorable.
If you have a trip in mind — or someone in your world who does — I’d love to help.
– Greg
Founder, Crux & Cairn
Preferred partnerships with leading hotel brands provide added value, such as room upgrades and amenities, enhancing your stay from the start.
Travel through
our lens
Behind-the-scenes planning, trip highlights, and destinations worth dreaming about.
@cruxandcairn
“I help clients move beyond the obvious options — identifying destinations, properties, and experiences that match their style, priorities, and how they actually want to travel.”
Ready to plan your
next great trip?
Tell me a bit about what you’re looking for and I’ll take it from there. No obligation, no sales pitch. Just a conversation about where you want to go.