The Ultimate Winter Road Trips in the U.S.

Winter road trips across the United States can take on various adventures: basking in the sun as you cruise into the Mojave Desert toward Joshua Tree, or navigating the snowy mountain paths of Vermont or Utah with tires equipped for the terrain. Traveling the Great American highways from November to late February can lead you to beloved destinations during their quieter seasons or to warmer, arid areas where temperatures are more moderate. January often sees lower prices, providing the chance to enjoy extended stays without the usual crowds. Your choice depends on what you seek: gourmet dining, national parks, cultural experiences, or all of the above.

With that in mind, here are six of the top winter road trips to embark on across the U.S., all thoroughly tested and endorsed by the Dinogo team and contributors.

1. Discover California’s Desert Landscapes

• Starting Point: Los Angeles
• Destination: Joshua Tree National Park
• Distance: 150 miles
• Recommended Duration: 4–5 days

While California’s Pacific Coast Highway offers a delightful experience in any season, venture inland for a taste of the state’s desert without the sweltering heat. From Los Angeles, travel east for approximately 100 miles on I-10 to reach Palm Springs. If you have a bit more time, consider taking I-60, a slightly longer yet more picturesque route that leads through Riverside, home to the historic Mission Inn Hotel and Spa, established in 1876. Any of the several dining options at the hotel provide a perfect spot for a photo-worthy lunch break.

Shift gears (both metaphorically and literally) after this upscale town and head toward Joshua Tree National Park. You don’t need to spend too long in the 1,242 square-mile park to appreciate its namesake twisted, spiky “trees.” However, we recommend at least an overnight stay in a Joshua Tree–area Airbnb: There’s a delightful range of choices, from refurbished Airstreams to a luxurious high desert lodge created by a protégé of Frank Lloyd Wright. Go for a hike, relax with a cold drink on a patio under the stars, and take a moment to appreciate the good life.

2. Journey Through Vermont’s Wintery Mountains

• Starting Point: Stowe
• Destination: Woodstock
• Distance: 130 miles
• Suggested Duration: 3 days
  

Vermont is often linked to autumn road trips, largely due to its famous leaf-peeping (is that term even still relevant?) attractions. However, in winter, the snow-covered mountains ideal for skiing take center stage. Consider this winter road trip in New England for a weekend getaway, featuring stays in Stowe and Woodstock, home to some of the state's most popular ski resorts.

The adventure begins in Stowe, where you can ski on 116 trails across the resort’s terrain. Savor an après-ski treat of raclette and whiskey at WhistlePig Pavilion off Spruce Peak, or enjoy live music at the long-standing Stowe hotspot, the Matterhorn, which has been “infamous since 1959.” For overnight accommodations, options range from the Austrian-themed Trapp Family Lodge, a family-friendly resort with an outdoor hot tub that fits 20, to well-furnished Airbnbs located in Stowe itself.

From there, drive approximately 40 miles east on I-89 to Burlington, a charming lakeside town with a population of 45,000. This town is perfect for relaxing after a day on the slopes at Stowe and offers various winter activities, such as ice skating in Arthur Park or enjoying the holiday lights on Church Street. Accommodations can be scarce in Burlington during the peak winter season, so it’s wise to book early. This Airbnb guesthouse, featuring a yard and deck, is among Vermont’s finest, conveniently located within walking distance of downtown Burlington, the waterfront, and the Church Street Marketplace.

On your third and final day, travel 90 miles via Highway 89 to reach Woodstock, a town situated near one of the oldest ski resorts in the country. Along the way, enjoy views of mountains such as Mansfield Mountain and seize the opportunity to stop by the Ben & Jerry’s factory in Waterbury.

3. Take a drive along Florida’s iconic “floating highway” to Key West

• Starting Point: Miami, Florida
• Destination: Key West, Florida
• Distance: 165 miles
• Suggested Duration: 2–3 days

Stretching from Miami all the way down to the southernmost point of the Florida Keys, this picturesque section of U.S. Route 1 traces the path of the historic Florida and East Coast Railroad. After a hurricane destroyed the tracks in 1935, the route was transformed into a highway a few years later. Today, it’s known by many names: the Overseas Highway, “the floating highway,” and the highway of 42 bridges. Each of these names accurately captures the essence of the journey, which often soars high above the stunning archipelago of around 1,600 islands, guiding travelers past swaying palm trees, pristine beaches, vibrant coral reefs, and crocodile habitats.

Start your journey in Miami, heading towards Florida City and the onset of “the Stretch,” an 18-mile stretch of Highway 1 that connects the mainland to the Keys. (Some travelers might take a detour to Card Sound Road for conch fritters at the iconic local biker hangout, Alabama Jack’s, although this road has been under repair in 2023.) Arrive in Key Largo via the Jewfish Creek Bridge, a 65-foot-high bridge offering breathtaking views of the Atlantic Ocean and Florida Bay. Here, you simply must indulge in your first slice of Key lime pie at Mrs. Mac’s Kitchen, a beloved local spot, before continuing to Islamorada. This village of six keys boasts one of the largest downtown areas between Miami and Key West; at its heart lies the Morada Way Arts and Culture District, a vibrant hub of shops and galleries, which hosts one of the Keys’ most lively Art Walks, featuring live music and late-night gallery openings every third Thursday from 6 to 9 p.m. Spend the night at the (newly opened in 2024) Postcard Inn Resort and Marina and enjoy a filling shrimp-and-grits breakfast at Green Turtle Inn before continuing your adventure.

Traveling with kids? Make a stop in Marathon, Florida, where you can explore Aquarium Encounters (get hands-on with coral-reef creatures through touch, feed, and tank dive experiences) and visit the Marathon Wild Bird Center, where you can see rehabilitated birds before they’re released back into the wild.

Your ultimate destination—Mile Marker 0—is Key West, a place where visitors can shop, snorkel, kiteboard, and fully immerse themselves in kitschy fun. There’s something for everyone in this vibrant locale; consider venturing off the beaten path with a Key West Food Tour. Don’t miss the famous six-toed cats at the Hemingway Home and Museum, and unwind with cocktails by the pool at the Southernmost Beach Resort.

4. Explore the historic cities of the South

• Starting Point: Charleston, South Carolina
• Ending Point: New Orleans, Louisiana
• Total Distance: Approximately 750 miles
• Recommended Duration: 10 to 14 days

Cities like Charleston, New Orleans (excluding the increase in visitors during Mardi Gras), and Savannah experience their low season in the colder months. Take advantage of off-season rates and lower humidity to explore the Gothic, antebellum, French, and various other architectural influences that shape these cities' unique character.

Begin your journey with a few days in Charleston, known for its exceptional culinary scene. (We highly recommend Charleston Culinary Tours—kudos to guide Dana Levine!—for an introduction to local flavors.) The city’s latest highlight is the impressive International African American Museum, located at Gadsden’s Wharf, where around 40 percent of enslaved Africans entered the U.S. Don’t miss the Old Slave Mart Museum for a candid exploration of Charleston’s history. The city also boasts numerous stylish boutique hotels, including the new Pinch and Loutrel, which we hope to visit on our next trip. (For more details, check out our complete Charleston travel guide.)

Feeling stuffed from all the Lowcountry cuisine? Make sure you save room for the next destination: Drive south on U.S. Highway 17 and I-95 for about 100 miles to reach Savannah, Georgia. The city’s majestic oak trees, draped in Spanish moss, create a hauntingly beautiful atmosphere, and its restaurants and hotels are bursting with character. Experience the vibrant energy of Savannah’s riverfront by staying at the 193-room Thompson Savannah. Opened in August 2021, this hotel was thoughtfully designed to be perpendicular to the Savannah River, enhancing its stunning views. It also features the city’s highest rooftop, further maximizing the scenic outlook.

Soon to debut is Hotel Bardo, created by the team behind Perry Lane Hotel, scheduled to open in early 2024; however, its Italian restaurant, Saint Bibiana, is already serving delicious meals. Locals in Savannah also rave about the food and atmosphere at Brochu’s, Common Thread, Dottie’s Market, the Wyld (with waterfront views), and the unique Strangebird, housed in a vintage Streamliner car. (Keep reading for more on the best things to do in Savannah.)

From Savannah, head towards the Big Easy along an inland route, passing through cities like Macon and Montgomery while exploring significant locations on the Civil Rights Trail. Set aside 1.5 to 2 weeks for this road trip to ensure that any additional stops can be enjoyed without feeling rushed.

Once you arrive in NOLA, make Hotel Peter and Paul your home base in the Marigny, just a few blocks from Frenchman Street (the heart of live music in New Orleans) and close to the French Quarter. Get ready for days filled with art, music, bourbon, and beignets. (Discover more about the best things to do in New Orleans.)

5. Explore the Christmas towns of Texas

• Starting Point: Grapevine
• Ending Point: San Antonio
• Total Distance: 355 miles
• Suggested Duration: 4–5 days

Texas’s larger-than-life charm doesn’t take a break during winter; Christmas fills its cities and towns with vibrant festivities and stunning displays.

Kick off your holiday celebration in Grapevine, the officially designated Christmas Capital of Texas, which hosts 40 days of festive fun just outside Dallas. While the North Pole Express might be sold out, the Christmas market at the Town Square Gazebo is bustling this month and offers a wonderful introduction to local artisans and craftspeople. After Grapevine, return to Dallas for an overnight stay at the Rosewood Mansion on Turtle Creek, a former private estate that has become a renowned Uptown hotel. (Alternatively, consider checking into the Joule, a modern boutique hotel rich in art and style located downtown.)

Although you could easily spend several days in the Dallas–Fort Worth area, if you're chasing the Christmas spirit, continue your journey the next day to Fredericksburg, approximately 262 miles to the south. The I-35 S will take you through Waco, so be sure to stop by Chip and Joanna’s Magnolia Market before reaching Fredericksburg. This historically German town offers a festive European twist with its traditional German Christmas Pyramid and the Christmas Nights of Lights every evening at the Marktplatz. Stroll along Main Street for shopping and book a night at Barons CreekSide, which offers a Texan version of a Swiss log cabin village set on a vineyard just minutes away.

The following day, continue your journey by driving 70 more miles south on U.S. 87 and I-10 to reach your final destination in San Antonio. Throughout December, the city’s River Walk transforms into one of Texas’s most renowned holiday hotspots. Enjoy a leisurely stroll along the river while admiring the vibrant lights and stay close to the festive activities at the Canopy by Hilton. This hotel boasts 195 rooms adorned with colorful art, textiles, and tilework that celebrate San Antonio’s rich culture and history, harmonizing beautifully with the city’s bright holiday decorations. Be sure to check out its open-air Otro Bar, where you can keep the festivities alive with a crafted cocktail and South Texas-inspired small plates.

6. Experience Utah’s “Big 5” national parks

• Starting Point: Zion National Park
• Ending Point: Arches National Park
• Total Distance: 380 miles
• Suggested Duration: 7–10 days

As per the National Park Service, around 70 percent of visitors flock to Zion National Park—Utah's most popular destination—between April and September. In contrast, the months from December to February see only about 2–3 percent of annual visitors each month. This means you can enjoy the park with minimal crowds, plenty of parking, and lower rates at remarkable places like Camp Sarika by Amangiri or trendy glamping spots such as AutoCamp Zion. (Keep in mind that daytime temperatures are typically in the 50s but can drop below freezing at night.) This is also a unique opportunity to see the striking red rocks of Utah’s parks contrasted against the pristine white snow—a sight often missed by summer tourists.

Like any road trip on this list, feel free to customize this journey to your liking. For this specific itinerary, set aside at least a week and begin your adventure near Zion National Park, using AutoCamp Zion as your home base. Then, take a two-hour drive east to Bryce Canyon National Park. Although it is one of the smaller national parks, Bryce boasts the highest concentration of otherworldly hoodoos on the planet. (In winter, stay at Bryce Canyon Lodge and in summer at Under Canvas Bryce Canyon.) Next, journey northeast for about two hours to Capitol Reef, a compact yet breathtaking national park. Experience its beauty along the 7.9-mile Scenic Drive, or extend your stay and spend the night at the Lodge at Red River Ranch. Complete your exploration of Utah’s “Big Five” by visiting Canyonlands and Arches national parks, another two-hour drive to the east. While these parks lack their own lodgings, Moab nearby offers several accommodation options.

There are also numerous excursions available outside of Utah’s national parks, along with seasonal activities—such as skiing in Bryce Canyon, which benefits from high elevation and offers consistent snowfall. This warrants an extra day or two on your itinerary.

Looking to add something extraordinary? Experience the luxury of Amangiri, featuring ultra-luxe suites, tents, and pavilions situated near Zion and Bryce. (Though it’s even closer to the confluence of Utah, Arizona, Colorado, and New Mexico, it’s easily accessible via Page airport in Arizona and is located very near Grand Staircase-Escalante National Monument.)

It’s crucial to keep in mind that winter road trips necessitate additional caution. Snow can accumulate, and storms may appear, rendering roads impassable at a moment's notice. Always ensure you are well-prepared and informed about conditions affecting your travel destination before setting off.

This article was first published in December 2022 and has since been updated with fresh information and recommendations on December 4, 2023.