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Visit Chicago, Route 66, Grand Canyon NP, Las Vegas, Los Angeles, The California Coast & San Francisco.
If you are struggling to decide whether to drive Route 66 or Highway 1, then why not go for this “combo” route. The Big Two itinerary chalks off both legendary roads on one epic three-week adventure.
Key road trip highlights:
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We’ll suggest properties to match your preferred budget, be it low-cost, mid-range or high-end luxury that you’re looking for. We can also mix it up so you’ll experience a range of standards and experiences along your road trip.
All of our American road trips can be tailored to meet your requirements. Do you have more or less than 21 days for your road trip? No problem, we can bolt on extra nights to allow more time to explore or shorten the number of destinations as required.
You’ll start your Route 66 road trip by spending three nights and two exciting days in Chicago. Many start by enjoying Chicago’s famous pizza or by going to the top of Willis Tower to watch the sunset and get the lay of the land. You’ll collect your wheels when you leave Chicago to begin the drive down Route 66. For now, you’ll be pounding the pavement from one outstanding attraction to another.
Most visitors to Chicago head straight to the ‘Magnificent Mile’, a vibrant, bustling area which is home to upscale shops, trendy restaurants and posh hotels. Landmarks include the historic Chicago Water Tower, the neo-Gothic Tribune Tower and the 100-story Hancock Center, which has a rooftop observation deck called 360 Chicago. Spend the rest of the day exploring some of the other attractions found north of the Chicago River. These include Navy Pier, Wrigley Field and the beaches along Lake Michigan’s shoreline.
On your final full day in Chicago, we recommend that you spend time visiting the city’s attractions that are located south of the Chicago River. Some of America’s very best museums are found here, including the Art Institute, the Alder Planetarium, and the Field Museum of Natural History. Be sure to stroll around Millennium Park; you’ll find world-famous outdoor artworks like Cloud Gate and Crown Fountain for those all-important Social Media snaps. Lastly, before leaving town, make sure you spend at least one evening partying at Buddy Guy’s Legends Nightclub.
Start your engines; iconic Route 66 awaits. After collecting your road trip wheels, we recommend you head to Jackson Blvd, where you can pass the small Route 66 sign that marks the beginning of your Mother Road adventure. Driving Route 66 through Illinois is super easy, as it’s really well-signposted and surprisingly rural once you’ve left the city of Chicago. Along the way to Springfield, you’ll enjoy highlights such as Route 66 obsessed Pontiac and the historic Standard Oil Gas Station in Odell. Once you arrive in Springfield, history enthusiasts will want to visit Abraham Lincoln’s Tomb, the Lincoln Presidential Museum and the Lincoln Home.
Onto St. Louis today, which sits on the banks of the Mississippi River. Highlights include the Missouri Botanical Gardens, Citygarden and the famous Gateway Arch National Park. If you have time, try to catch a baseball game here at the Cardinals stadium, which is located right in the heart of the city. Remember that you’ll be provided with a detailed Road Trip Pack, which will guide you through all the Route 66 roadside attractions and much more.
Today, you’ll continue southwest through the State of Missouri. En route, we recommend you stop by Meramec Caverns, which are located in the Ozarks region. These vast caverns are an extensive set of limestone caves offering unforgettable underground tours. You’ll finish the day in Springfield, Missouri, which is officially recognised as the birthplace of Route 66.
Get an early start and continue along the Mother Road to Tulsa. You’ll pass through Joplin before skimming through a corner of Kansas and into Oklahoma. In Tulsa, we recommend visiting the Philbrook Museum, home to a vast art collection housed in an Italian-style villa surrounded by idyllic gardens. During the afternoon, you’ll continue onto Oklahoma City. Visit the Bricktown District for an evening meal at one of the numerous diners and restaurants. Lastly, before turning in for the evening, consider visiting the Oklahoma City National Memorial, which remembers the victims and survivors of the 1995 Oklahoma City bombing. This perfectly executed dedication is especially moving at night.
Spend the morning at the incredible National Cowboy and Western Museum before checking out the real-life cowboys over in Stockyard City. If you still have the energy, then the daring amongst you should check out some of the activities at Riversport Adventure Park. Our amazing Road Trip Pack will show you the way to Amarillo. You’ll pass some fantastic Route 66 museums along the way, packed with nostalgic Americana, classic cars and more. Once you hit Amarillo, there’s only one place for any true road-tripper to go for dinner. The Big Texan Steak Ranch & Brewery is simply a must, just make sure you arrive hungry, as the portions are HUGE!
Today’s drive are packed with classic Route 66 attractions like Cadillac Ranch (pictured), The Midpoint Cafe and the Route 66 Auto Museum in Santa Rosa. You can then opt to finish the day with an overnight stop in either Albuquerque or Santa Fe. We’ll talk you through the pluses of both options when you request a quote from us. Santa Fe lies on the old or original Route 66 route, offering an upmarket spa town feel. Albuquerque lies on the newer, more direct route and is famous for the Sandia Peak Tramway and “Breaking Bad” filming locations.
El Morro is a detour worth considering to see ‘inscription rock’, a large sandstone pueblo where travellers since the 17th century have left messages. Later in the day, you’ll pass through two Natural Wonders – Painted Desert (pictured) and Petrified Forest National Park, before getting your head down in the classic Route 66 overnight stop of Winslow in Arizona.
The awe-inspiring Grand Canyon is located one hour’s drive north of Route 66. The world’s largest and most famous geological wonder is simply staggering. Two billion years in the making, the Colorado River has forged a mile deep, 18 mile wide and 277 mile long slice into the Arizona landscape that will stay with you forever. Before leaving Route 66 however, you’ll get the chance to experience another natural wonder in the form of Meteor Crater. Not as large a hole as the Grand Canyon, but in many ways just as spectacular and intriguing.
Again, it’s not strictly on Route 66, but Las Vegas is so close that it would be rude not to pop by and say hello. Along the way, you’ll pass by some iconic Mother Road locations like Seligman and Hackberry General Store. As you get closer to Vegas, you’ll pass over the Hoover Dam before seeing the bright lights of Las Vegas in the distance.
If your head hurts after a big night out, then why not chill out by one of the fantastic swimming pools that adorn every hotel. Alternatively, you can explore the legendary ‘Strip’ and book tickets to see an outstanding show. Witness the Bellagio Fountains in full flow, or take a Gondola ride at the Venetian. A visit to The Neon Museum might appeal, where you can experience the Las Vegas magic of a bygone age by touring the Neon Boneyard. Whilst, driving enthusiasts might want to test their skills at Speed Vegas, where you can drive supercars around a thrilling race track. Want more time here? Then just let us know.
The iconic Santa Monica Pier signals the final stop of your Route 66 holiday. To celebrate the finale of your journey, we suggest you enjoy a rewarding meal at one of the Pier’s many eateries that overlook the Pacific Ocean and take a picture by “The End of Trail” sign. After lunch, we suggest you take a stroll and explore Santa Monica and neighbouring Venice Beach.
Spend the day relaxing by the pool after your Route 66 adventure, or head out to explore the sites of Los Angeles. There’s plenty to keep you busy. Hollywood is synonymous with glitz and glamour, and it’s the most visited part of the city. The Griffith Observatory is just a short drive northeast of here, perched high on a hill overlooking the urban sprawl. This famous landmark is well worth visiting and offers excellent views of the legendary Hollywood Sign. Universal Studios and Warner Bros Studios are close by also.
You might want to just relax by the hotel pool on the final day in Los Angeles. Alternatively, you can head for Beverly Hills to try and find your favourite celebrities home or bump into them whilst shopping on Rodeo Drive.
It’s time to explore the second iconic road of this holiday. Whether you call it the Pacific Coast Highway, Highway 1 or the Cabrillo Highway, you won’t be disappointed by this 400-mile stretch of stunning road. Today, you’ll leave Los Angeles and pass by Malibu on your way north to Santa Barbara; this charming Mediterranean-style town is one of the Central Coast’s top highlights. Stroll along historic State Street, visit the Santa Barbara Botanic Gardens or enjoy the town’s beautiful beaches.
Today, you’ll make your way up to beautiful Carmel, located at the southern end of Monterey Bay; along the way, you’ll experience the stunning natural beauty of Big Sur and discover why people hold the Pacific Coast Highway so dear to their hearts. Carmel is a charming place that offers two world-class beaches backed by a small town of beautiful homes, quaint streets, and fabulous restaurants. The wild and wonderful Point Lobos is just a few miles south of Carmel. This small State Park is unique and can be enjoyed on short, manageable hikes.
In the morning, we suggest you cruise around the famous “17 Mile Drive” while heading to neighbouring Monterey. You’ll pass millionaire mansions, Pebble Beach Golf Club and a stunningly beautiful rugged coastline. Monterey was once California’s capital, but today, it’s best known for the world-class Monterey Bay Aquarium located on Cannery Row. Want to experience the Bay up close? Then we highly recommend you take a whale-watching trip from Fisherman’s Wharf, as Monterey is considered one of the best places in the world for this activity.
The last leg of this epic road trip along Route 66 and Highway 1 awaits. Take the short drive north to San Francisco, and you’ll pass by the retro surf town of Santa Cruz and the picturesque Pigeon Point Light Station. During the evening, enjoy a meal in one of the city’s wonderful restaurants before settling in for the night. Get a good night’s sleep; you’ll need your energy for the next day and a half of sightseeing in this fabulous city.
Once the fog lifts, one of America’s favourite cities will be revealed. Ride a cable car, climb the streets, and get into the vibe only this city offers. San Francisco is packed with Victorian charm, famous movie locations and world-leading tech companies. San Francisco has it all.
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You’ll find answers to most of your questions right here. If you still need assistance, Feel free to get in touch, and we’ll be sure to get back to you promptly!
Not a problem. If you are lucky enough to have extra time to explore more places or add more rest days, then just let us know and we’ll adjust your trip to match your preferred timescale.
We strongly advise that you purchase travel insurance for your holiday to cover you against medical expenses, theft and other financial costs. Should you need to cancel before travelling, some insurance policies may pay out for any loss of funds that have been paid to us and which cannot be refunded under our cancellation policy.
Many of our trips have a different end destination than the starting point, so this is not a problem. Please note a fee sometimes applies for one-way rentals between other regions or states, which will be paid to the supplier directly when collecting the vehicle. We’ll endeavour to inform you of this charge within your quote.
No, far from it. We work with a range of properties from 3* to 5*, so we can adapt the trip to match most budgets. We have access to rooms in more than 800 hotels, motels, lodges and B&Bs across North America.
The minimum age to rent a car is 21 in the United States or Canada, although, in addition, any drivers under 25 years of age will generally incur a surcharge.
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