There are some trips designed to help you see more, and others that remind you to slow down enough to actually experience where you are.
This month, Vincent and I headed to Jackson Hole with our friends at Robb Report and the RR1 community for a few days centered around beautiful design, incredible food and the kind of outdoor experiences that make Wyoming so special. Our home base was Hotel Yellowstone, a luxury retreat overlooking the surrounding landscape and an ideal starting point for experiencing the Tetons, Snake River and Jackson Hole in a completely different way.
Planning a trip to Jackson Hole? Here’s our takeaway from the itinerary.
Set above Jackson Hole, Hotel Yellowstone feels like exactly the kind of place I want to return to after a day outside—refined, intimate and deeply connected to its surroundings. The property embraces the beauty of the West while serving as a jumping-off point for everything from Grand Teton excursions and fly fishing to hiking, scenic floats and stargazing.
For me, the best hospitality deepens our connection to a destination and shapes how we experience it long after we’ve returned home.
Fly Fishing the Snake River
We’re started our first full day in Wyoming on the water with a morning of fly fishing, something neither the scenery nor the schedule allows you to rush. Jackson Hole is known for world-class fishing for a range of experience levels, and I love the idea of beginning this trip standing in the Snake River, learning something new and paying attention to an entirely different rhythm.
There is something wonderfully restorative about an activity that requires you to be present—particularly after a season filled with planes, meetings and events.
After a morning outdoors and a little time to explore Jackson Hole, we gathered for dinner at Wild Sage. I always believe food is one of the best ways to understand a destination, so we definitely embraced an evening that feels distinctly Western—seasonal ingredients, great wine, warm hospitality and, most importantly, time around the table with friends.
These are often the moments from a trip that stay with me longest.
E-Biking Through the Tetons
Saturday began on two wheels as we headed out for an e-bike ride through the Tetons. Jackson Hole’s network of pathways makes biking an incredible way to experience the scale of the landscape—you’re moving through it rather than simply observing it through a car window.
I was especially excited about seeing the mountains this way in early Fall, when the air is crisp, the crowds begin to shift and the landscape starts telling a different seasonal story.
A Little Afternoon Luxury
The afternoon shifts from outdoor adventure to some decidedly different forms of exploration: lunch, a series of automotive experiences and a private appointment with Isaia before ending the evening with a LOUIS XIII nightcap. I love that the itinerary juxtaposes rugged Wyoming with beautiful craftsmanship and luxury—because for me, travel is most interesting when it isn’t one-note.
Turns out, a great day can include dirt on your shoes, beautiful tailoring, an extraordinary meal and a very good glass poured at the end of it.
Final Thoughts & Reflection:
The Art of Getting Away
More than anything, this trip is an opportunity for Vincent and me to truly step away for a few days. The work will still be there when we return, but so will a very full Fall ahead. I’m increasingly convinced that experiencing new places, trying things outside our everyday routines and simply having time together aren’t breaks from creativity—they’re part of what fuels it.
Jackson Hole felt like the perfect place to put that philosophy into practice.
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