Summer in the world's best mountain destinations

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.

My girlfriends and I were looking for a place for a girls getaway. Our goal was great outdoor experiences and relaxed but attentive service. We wanted something a bit different this year. One friend had been to Utah before and mentioned she had a fabulous time. Of course, many of us have been skiing in Utah, but it is spring, and all the snow has melted. We were not convinced there would be anything to do. After some searching, I found out that Utah is the first state to be given three Michelin Stars!

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.”

There is a semi-secret spot at the Jerome on the fourth floor balcony that is a great place to have a drink, watch fireworks or see the sun set down over the valley. It’s a hidden nook and it’s just a sweet place to get some fresh air and look out at the Aspen mountains. You might even find Tony, our General Manager, up there taking in the beauty of this amazing town, which never gets old - which Tony should know as he as been here 35 years. PS: Don't let him know that I told you about his secret spot.

A word of warning for parents— your kids are one Junior Je-Roamer trip away from breaking your croquet winning streak, taking the "ski-ripper" family title, or showing you up at fishing. Aspen may be an adult’s paradise, but it doubles as a kid’s disneyland. While there are a myriad of adventures to explore, a Je-Roamer favorite is T-Lazy-7 Ranch, where winter is for suiting up to tour the white wonderland via snowmobile, and summer months are remembered for riding horses through Maroon Creek Valley and catching a trophy-sized rainbow trout while fly-fishing for the first time. (Don’t worry, young in age or young at heart, all are welcome.)

The roar of the Upper Piedra River is loudest when the cold, hard snow begins to melt in Telluride. So in late May, adrenaline junkies head straight for the river’s frigid Class IV rapids. “Spring runoff turns the Piedra into a raging river, perfect for intense white-water rafting,"...

There are two things each new season in Telluride is sure to bring: a change in weather and unparalleled festivals. In my opinion, Telluride's smaller, lesser-known festivals are some of the town’s best-kept secrets. Take, for instance, the quirky Mushroom Festival. Here me out— it’s a celebration of full of cooking demonstrations, guided hikes for mushroom identification, and a parade where attendees get creative with fungal-themed costumes.

At the annual Blues & Brews Festival, September sunlight saturates mountains cloaked in green and gold trees—setting a colorful stage for three days of funk, rock, soul, and blues. “This event is overshadowed by all the other Telluride festivals,” says General Manager Alex Rollinson. “But it’s my favorite—and one of the few family-friendly options where kids 11 and under are free.

“Just breathe,” he told himself as he navigated Telluride’s thrilling trek. Studded with steel rungs and strung with ropes, Via Ferrata—one of the few of its kind in the U.S.—soars 2,000 feet high and offers aerial views of a tree-littered valley and the town. The adrenaline-pumping, two-mile expedition includes navigating a rock wall, walking along a sheer cliff trail only a foot wide...

I don't just plan trips, I change lives. When a couple comes to me in need of a romantic getaway, it's especially exciting to plan a travel experience that is not only out-of-the-box and inspiring but that also stops time. An insider tip I love to give my clients is the special opportunity to make their own scrubs at Hacienda AltaGracia's spa. The team of massage therapists assist you in mixing your bathtub blend with lush tropical oils, bottling the scent of Costa Rica for you to take home.

Locals lovingly call them 14ers—the majestic, rugged mountains rising above 14,000 feet that are heavily concentrated in Colorado, which has the most of any state. The quest to dominate these treacherous summits has captivated many adventurers. “The Telluride area has 14 of the state’s 53 peaks,” Troy Trinh says. “My favorite, Wilson Peak, happens to be one of the toughest. You might recognize its northern face from the Coors Light can.”

The San Juan Skyway is a 236-mile loop that incorporates the famous Million-Dollar Highway, the most famous portion of which travels from Ouray to Silverton (US 550) over Coal Bank Summit and the Molas Divide. The route includes five passes, countless ghost towns and a smattering of some of the finest mining remnant towns in the West

I've been traveling to Costa Rica for almost 30 years, and I've been to plenty of the country's resorts. In all that time, I've never seen a place where both kids and adults can have equally incredible experiences than at Hacienda Alta Gracia. For kids, the stables are the best in Central America. Well-trained and easy for kids to ride and enjoy, my granddaughters fed and brushed the horses following their ride. Plus, a huge bonus - there are almost always baby horses on the property, which are always a hit! Back at the resort, the kids played at Kata Grande, conveniently located near a bar where parents can enjoy!