My wife Maggie and I are Co-Captains of the Banquets Team, where you will usually find us presiding over wedding receptions and corporate events, orchestrating all the minute details from setting up 12-piece place settings to making sure the procession of courses and wine pairings goes smoothly. But I also lead a double life. As many mornings as possible, I soar like a bird high over Aspen as a paragliding instructor. It’s the most exhilarating feeling to see the four ski mountains—Aspen, Snowmass, Highlands, and Buttermilk—and the entire valley from such a high vantage point.

We specialize in events all over the world. With offices in both Costa Rica and Colorado, we work with clients seeking very different weddings. With the world as your oyster, narrowing down a destination wedding venue can be challenging, albeit exciting. It’s my job as a destination wedding planner to help our clients see their vision come to life in a setting that’s perfect for them. Over the years, I’ve created a formula for getting us to the right place. Follow these guidelines and you’ll be celebrating in paradise in no time!

I moved to Aspen last summer and soon adopted the same ritual as a lot of locals I know: trekking up Smuggler Mountain for an invigorating morning hike. The usual reward is a sweeping view of the town of Aspen and the Roaring Fork Valley from the observation deck at the summit. But on my last trek, I found another reward far sooner. Just off the first turn, I spotted a wooden swing carved with the words #AspenSwingProject. Whether you use it for a short rest, or pump your legs for a childish thrill like I did, the swing truly is a “random act of kindness.”

To the rest of the country, Hunter S. Thompson might be best known as the godfather of gonzo journalism. Thompson lived and wrote on the edge in a style epitomized in “Fear and Loathing in Las Vegas,” which first came out in two installments in Rolling Stone before being published as a book that would end up defining the post-'60s counterculture. But to Aspenites, and especially here at Hotel Jerome, he’s best remembered for his 1970 run for sheriff of Aspen Pitkin County.