Festive Family Adventures in New York, Aspen & LA

Few places offer such a diversity of landscapes and experiences as the United States. This luxury winter adventure crosses from east to west, from city to slopes to sea. Along the way you’ll soak in New York’s holiday festivities, take the train to the nation’s capital, before hitting the powdery slopes of Aspen, ending your journey on the Pacific Ocean in sun-kissed Los Angeles.

New York City

Days 1 – 5

From elaborate window displays and sparkling lights decking every surface, to festive skaters whirling across the ice in Central Park and Rockefeller Center, New York City is especially magical during the winter holiday season. We’ll make sure you have front row seats to those can’t-miss spectacles, such as the iconic Rockettes Christmas Spectacular or The Nutcracker at the New York City Ballet, and be sure you have those hard-to-get restaurant reservations, but we’ll also take you beyond the expected. 

We’ll pair you with a local Brooklynite in Domino Park for an exploration of Williamsburg by bicycle, discovering boutiques, pop-ups, street art, and cafes. For art lovers, you can expect a private look behind the scenes at galleries and studios, as well as a personal guide at the best museums, from the Met to The Frick. With hot chocolate in hand, a private chauffeur will drive you through Dyker Heights to soak in its iconic Christmas display. 

Washington D.C.

Days 6 – 8

Washington D.C. is just under three hours away on the Acela Express Train. America’s capital city is famed for its historic landmarks, and your private guide will be a local with a deep understanding of the places you’ll be seeing– including of course landmarks such as the Lincoln Memorial and Library of Congress, but also lesser known spots such as the powerful Korean War Veterans Memorial. The Smithsonian is renowned for being the world’s largest museum, education, and research complex. With twenty-one museums (and the National Zoo) represented, we’ll arrange an excellent guide to expertly direct you to points of interest– based on what your family is interested in. Your stay at The Jefferson Hotel is a stately slice of D.C., located in a 1920’s apartment building between the White House and Dupont Circle. It’s close enough to walk to all of the best attractions, but far enough to be out of the thick of it all. 

Aspen, Colorado

Days 9 – 15

Next, it’s away to the Rocky Mountains to revel in Aspen’s winter wonderland. This little mountain town’s reputation as the place to see and be seen precedes itself, but you’ll also find characterful Western roots alongside the designer storefronts. With the exceptional Little Nell as your homebase (one of our favorites), you’ll have both prime access to the slopes and a luxurious bolthole to put your feet up at the end of the day. The hotel sits at the bottom of Aspen’s Ajax Mountain and is the only ski-in ski-out hotel in town, plus the team’s ski concierge will transport your family and all your gear to any of Aspen’s four mountains. For an unforgettable powder day, we’ll arrange a snowcat to take you for runs down the untracked snow of the backcountry of Aspen Mountain. 

Although skiing is the highlight, Aspen also has a lot to offer beyond the slopes. Take a horse-drawn sleigh to a gourmet dining experience in a cozy, remote hut in the Elk Mountains at nearly 10,000 feet elevation. The food is focused on local Colorado fare, like Rocky Mountain trout and wild elk. Snow shoeing, ice skating, and dog sledding are just a few more of the unique winter experiences we have up our sleeves. 

Los Angeles

Days 16 – 18

When you’ve had your fill of snow, head to Los Angeles to end your coast to coast journey with some winter sun. Southern California’s winters are famously mild– the perfect sunny weather for riding around town in a restored 1976 Cadillac Eldorado. Spend a day exploring Beverly Hills, Bel Air & the Hollywood Hills, cruising along iconic Sunset Boulevard with the top down and wind your way through the hills of Bel Air.

Your stay at The Maybourne is the first U.S. outpost from the group behind legendary London hotels, the Connaught and Claridges. In the heart of Beverly Hills and steps from Rodeo Drive, the freshened design and a step up in service has taken a great hotel and turned it into one of our favorites in Los Angeles. Rooms are bright and classic with a mid-century twist and the rooftop pool is the perfect place to spend a lazy afternoon. Mountain biking alongside stunning Pacific Ocean views in Malibu, a fast pass to Universal Studios, and a night gazing at the twinkling city lights and vast galaxy of stars at the Griffith Observatory are all wonderful possibilities for the end of your journey.  

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