- Travel
5 Ultimate Road Trips to Take
in the United States
- August 3, 2022
Few experiences are as freeing as a pleasure-filled, wind-in-your-hair road trip that takes you from one fantastic spot to another. Whether driving past miles of rolling vineyards, awe-inspiring mountain landscapes, or stunning water views, these journeys ignite our sense of adventure and remind us that there is beauty and wonder to be found in our own backyards. Here’s why the following five vacations are KEY favorites.
1. The Pacific Coast Highway
The Pacific Coast Highway is one of America’s most famous and most beloved roads. Between the perfect weather and the perfect views, it’s hard to top this trip.
What to do in Santa Barbara
Santa Barbara is a coastal beauty with delightful village ambiance and California-cosmopolitan amenities like great food and exclusive resorts. Start your morning with breakfast at Jeannine’s, a beloved institution serving up filling comfort food and decadent pastries, then explore Old Mission Santa Barbara. Built in 1786, this landmark is home to a community of Franciscan friars and an active church. Visit this so-called Queen of the Missions’ museum, cemetery, and the twelve acres of lush gardens. Foodies should absolutely plan for a sampling tour of Funkzone, the city’s trendiest nabe, with a culinary tour and your own KEY guide. Or let us handle dinner reservations for your party at The Lark, a true farm-to-table delight. The entire family will love feeding the giraffes at the Santa Barbara Zo and the thrill of KEY-arranged paddleboard adventure or private horseback beach ride.
Along the way…
Marvel at Hearst Castle in San Simeon (the site gets 750,000 visitors annually) or play at the Santa Cruz Beach Boardwalk, a classic seaside amusement park that has a retro feel, tons of fun rides, and that authentic beachy boardware fare you can’t get anyplace else.
What to do in San Francisco
San Francisco has it all—vibrant culture, world-class food, and stunning natural beauty on all sides. KEY’s unique sailing trip with a stop in the charming Sausalito is a special way to see the city and glimpse the Golden Gate Bridge. Don’t miss the massive China Live, the new restaurant and retail space in the heart of Chinatown, or the amazing works of art on display at the San Francisco Museum of Modern Art. End your day with dinner at Michelin-starred Californios (with a meal dished up by People’s sexiest chef Val Cantu) or let KEY’s private chef bring dinner to you.The Overseas Highway (US 1) is known as “the Highway that Goes to Sea” and it’s your ticket to an incredible ride from Miami to the Florida Keys. This mostly two-lane highway was built on an old rail bed, and it’s an amazing opportunity to see some of the Sunshine State’s most epic scenery.
2. The Peninsula of Florida
What to do in Miami
We’ll arrange a private art tour of the Wynwood Art district, home to over 70 galleries, museums and collections. Dine at Alter, named Miami’s most exciting new restaurant by Bon Appétit. Alter’s food is prepared by the award-winning Chef Bradley Kilgore, with a bold and exciting menu that draws from the locally-sourced seafood, fruits, vegetables and meats. See what makes Miami specia: its urban landscape and the wild beauty of the Everglades with a seaplane and airboat adventure.
Along the way…
You’ll be driving past the Florida Keys National Marine Sanctuary, which protects an impressive 2,900 square nautical miles of waters surrounding the Florida Keys, from south of Miami westward to encompass the Dry Tortugas. Book a dive or snorkel trip via one of the Blue Star Operators (even better, let KEY arrange the trip for you). These operators are committed to coral conservation, so you’ll know you’re doing right while you have the underseas experience of your lifetime.
What to do in the Keys
Keep driving south until you hit Key West, where the average yearly temperature is a balmy 77 degrees. Take the kids to Key West Aquarium and get up close and personal with marine life. If you’re interested in American history and literature, you’ve got to see the Ernest Hemingway Home and Museum, the former home of Key West’s most famous, fascinating resident. Need the ultimate selfie for your Insta feed? Mile Marker 0, baby
3. The Country Roads of Texas
From the Live Music Capital of the World you can follow a sea of bluebonnets and Indian paintbrushes to some of the most picture-perfect small towns found anywhere. Discover the juiciest peaches, taste some of the best barbecue, find one-of-a-kind antiques, and taste delicious Texas wine with the friendliest people around.
What to do in Austin
Experience true Texas BBQ with a tour of four of the tastiest barbecue joints in the state, then a pitmaster will teach you to prepare and smoke authentic Texas barbecue. That evening, KEY will secure you tickets to ACL Live, the influential music series with consistently sold-out shows—upcoming artists include Bon Iver, St. Vincent, and Willie Nelson. Look your finest while kicking up your heels in a new pair of cowboy boots, courtesy of KEY’s custom boot fitting and whiskey tasting, and a pampering blowout. After the show’s over, your night doesn’t have to be. Explore what Austin’s 2nd Street District has to offer before your private driver whisks you back home.
Along the way…
KEY has an all-day Hill Country Wine Excursion all planned out for you and yours. During your seven-hour trip, you’ll tour three wineries, each offering deliciously unique wines for your sampling pleasure. Spend the next day on a private Texas ranch, beginning with a 90-minute horseback ride with an experienced guide. Enjoy a lesson in tomahawk and knife throwing or archery, or access the ranch, pool, natural hot springs, waterfalls and hiking trails.
What to do in Fredericksburg
Fredericksburg may not have the population of other, larger Texas cities, but there’s an abundance to do and see in this historic central Texas destination. Climb the granite dome, explore rock formations, and hike the trails at Enchanted Rock State Natural Area. Visit the nation’s largest working wildflower farm, Wildseed Farms. Tour the National Museum of the Pacific War which preserves the legacy of Fleet Admiral Chester W. Nimitz and the others who served in the Pacific-Asiatic Theater of Operations during World War II.
4. The Colorado Mountains
Though Aspen and Vail are famous for offering skiers and snowboarders some of the best winter delights anywhere in the world, we think both of these beautiful locales offer visitors plenty to do all year long.
What to do in Aspen
If you’re in Aspen during the winter, KEY’s team can help you secure a ski valet, arrange a horse-drawn sleigh ride to the base of the Elk Mountain Range, or get you set up an exhilarating dog sledding experience. During warmer months, enjoy an afternoon of fly fishing followed by a picnic lunch, or a pampering day of private yoga, de-stressing massage, and a chef on duty to prepare your ideal meal.
Along the way…
The midpoint of your drive between Aspen and Vail is Glenwood Springs, a city situated in the Rocky Mountains famous for its hot springs. Don’t miss Glenwood Hot Springs Resort, home of the world’s largest hot spring pools. In addition to the healing, soothing waters, the resort includes a spa, fitness center, and a 107-room lodge. Take a walking cave tour at the Glenwood Caverns Adventure Park and marvel at the activities, stalagmites, soda straws, cave bacon, and flowstone.
What to do in Vail
Ice fishing, snowshoeing, and a guided backcountry skiing tour are just a few of the winter offerings KEY can arrange. In the summertime, Vail’s still a dream spot for the outdoorsy types. KEY will secure mountain bikes for your group so you can see Vail Mountain in all its glory. Take a gondola ride to a beautiful hiking spot on the Vista Nature Trail. It’s not only outdoor fun, though. The new Blue Starlite Dine-in Movie Theater and Cinema Supper Club promises a wild, quirky, and totally unique movies + more experience!
4. The East Coast of New York
Okay, calling the actual drive spectacular is a bit of a stretch, because the most direct route to the Hamptons is the Long Island Expressway, and it’s not much to look at. But considering some of the world’s most beautiful beaches are only a few hours from one of the world’s greatest cities means we’d be remiss not to mention this road trip. Though there’s a rough beauty to the Hamptons in the winter and fall is a leaf-peeper’s paradise, to really enjoy the surf, sun, and scene, visit at least once during peak summer season.
What to do in New York City
KEY already has your perfect New York City day outlined here. We’re all about arranging your perfect Central Park excursion, a night on Broadway with access to the cast; restaurant reservations at the hottest spots; and a private driver to spirit you around the city that never sleeps.
Along the way…
Since the actual journey from the city isn’t that far, you’ll have plenty of time to visit one of the area’s vineyards on your way out east. Try the award-winning wines of Riverhead Martha Clara Vineyards, built on the site of a former potato farm. For a slightly sillier stop, say hello to The Big Duck, a building in Flanders listed on the National Register of Historic Places.
What to do in the Hamptons
If you’re visiting the famous South Fork in the summer, be prepared to spot superstars like Leo, Gwenyth, or Beyoncé. Maybe you’ll see one of them on the beach while you’re enjoying your private surf lessons and picnic or dining alongside you at trendy restaurants Highway (from the same team that brought you Eleven Madison Park) and Calissa. Make a stop in Southampton for luxury shopping and to explore the art scene. Jackson Pollock and Roy Lichtenstein both had studios here, and there are galleries galore to pop in and out of throughout the village. Hop over to Water Mill to see the Parrish Art Museum, with over 2,600 works from Jackson Pollock, Lee Krasner, Willem de Kooning, Jane Freilicher, April Gornik, Cindy Sherman, and Chuck Close.
