Classic Route 66: Retro Stops & Vintage Vibes 

Get your kicks on a journey along the legendary Route 66, stretching from the bustling streets of Chicago to the sunny shores of Santa Monica. This iconic road trip winds through small towns, wide-open plains, desert landscapes, and historic cities, offering a mix of adventure, nostalgia, and unforgettable sights.

Along the way, discover quirky roadside attractions — from towering statues like the Gemini Giant to the colourful Cadillac Ranch, vibrant Route 66 murals, and classic neon signage.

Stay in unique Americana accommodations, including retro motels like the Blue Swallow Motel in Tucumcari, vintage motor courts, and historic Harvey Houses such as La Posada Hotel in Winslow, each offering a glimpse into mid-century roadside culture.

This is more than a drive — it’s a celebration of Americana, local history, and one-of-a-kind experiences. Snap photos at legendary stops, savour local diners and eateries, and immerse yourself in the nostalgia, charm, and character that make Route 66 a truly iconic journey.

This USA holiday can be tailored to suit your exact requirements, so just let us know your ideal trip.

Everything can be adjusted to suit your needs and create your perfect USA holiday.

Is this a Private Tour or a Group Tour?

All of our USA tours are private, tailor-made itineraries, designed around your preferences. We can adjust every element to suit your interests, pace, and travel style. This particular USA trip includes flights, accommodation, and car rental (where applicable).

What are the Departure Dates?

Since this is a private trip, there are no set departure dates. Let us know your preferred dates of travel, and we will find the best flights to fit your itinerary. We can advise on the best times to visit each region of the USA, as well as periods to avoid due to peak tourist seasons, inclement weather, or when travel would simply be better timed for your itinerary.

Which Airlines do you use?

We work with all major airlines flying to the USA. Depending on your departure city, we typically suggest carriers such as Virgin Atlantic, British Airways, and Delta. If you have a preferred airline or route, just let us know. We can also organise flights from any regional UK airport. There are direct flights from the UK to many US hubs including New York, Los Angeles, Miami, and San Francisco.

Which Hotels do you use?

We carefully select hotels based on location, style, and quality, but we are guided by your preferences. We specialise in boutique hotels, charming historic properties, and smaller luxury hotels where available. In major cities like New York, Chicago, or San Francisco, hotel rooms can sometimes be smaller and more expensive, and many properties lean towards a more business-style design. If room size or character is important to you, please let us know and we can suggest alternatives.

We also consider proximity to attractions and transport links, as driving or using public transport in large cities can add travel time.

Please note that many US hotels charge resort or facility fees (covering amenities such as Wi-Fi, fitness centres, or pools). We try to include these in our pricing wherever possible, but as policies vary by hotel, we recommend checking with us for details at the time of booking.

Car Rental & Driving in the USA

Many of our itineraries include car rental to explore regions at your own pace. Rental cars give you freedom, but there are a few practical points to note:

• One-way fees: Some itineraries involve picking up a car in one city and dropping it off in another. One-way fees can apply, depending on the rental company and locations. We will try to include these where possible.

• Parking: City hotels may charge for parking, and rates can vary. We will guide you on likely costs.

• Insurance & Navigation: We can advise on the best insurance coverage and suggest GPS or app-based navigation for ease of travel.

• Driver Requirements: A valid driver’s licence is required. For most rentals, an International Driving Permit (IDP) is recommended, particularly if you plan to drive across multiple states.

Ask us for more details so you can plan your trip with confidence.

Isn’t the USA expensive now?

Well, it depends on where you go! The USA offers incredible variety, from budget-friendly options to luxury experiences. We plan your trip to balance value and comfort, helping you get the most out of your accommodation, transport, and excursions. Many of our itineraries include car rental, which gives you the freedom to explore at your own pace and discover hidden gems off the beaten path.

There’s plenty to see and do without spending much, from scenic drives and hiking trails to charming small towns and local markets. Entrance fees to national parks, museums, or attractions are generally reasonable but vary by location. Private guided trips can be more expensive, but there are also plenty of small-group options available, which allow you to enjoy expert guidance while keeping costs manageable.

We can mix and match this to suit your itinerary. Dining in the USA can suit every budget — from food trucks and diners to world-class fine dining.

Chicago

As the largest city in the Midwest, Chicago is the quintessential American city with a surprisingly homey atmosphere.

From its exquisite lakefront views to its world-class dining and cultural delights, the US’s ‘second city’ consistently proves itself to be a first-rate destination which is second to none.

Visitors will discover a wide range of landmark museums, iconic architecture, and thriving comedy, theatre, and blues scenes. While outdoor enthusiasts explore the picturesque pathway winding along the Lake Michigan coastline, or join a volleyball game at sprawling North Avenue Beach, culture aficionados can admire works by the likes of Picasso and Miro in the city’s world-class galleries.

With its wildly diverse neighbourhoods drawing on influences from around the world, the Windy City truly has something for everyone. No matter, your age or interests, you are unlikely to experience a dull moment in the vibrant metropolis of Chicago.

Springfield, Illinois

As the capital city of Illinois, Springfield offers a captivating blend of American history and classic Midwestern charm. Most famously known as the home of Abraham Lincoln, visitors can step back in time by exploring the Abraham Lincoln Presidential Library and Museum, his preserved home, and the historic Old State Capitol where he once served.

Beyond its presidential heritage, Springfield boasts a friendly, small-town atmosphere with plenty to see and do. Stroll through the scenic Washington Park Botanical Garden, take a boat out on Lake Springfield, or enjoy one of the many local diners that keep the spirit of classic Route 66 alive.

As a key stop along the Mother Road, Springfield is filled with nostalgic roadside attractions, vintage neon signs, and timeless Americana that transport travelers to a bygone era.

St. Louis, Missouri

Resting on the western bank of the mighty Mississippi River, St Louis is a major city in the southern state of Missouri and the largest city in the scenic Great Plains area.

Whether you are keen to enjoy some baseball, bowling and beer or some rich local culture and history, this vibrant city has something to offer just about every type of visitor.

The main attraction is undoubtedly the iconic silver Gateway Arch. This impressive feat of engineering was built in honour of explorers Lewis and Clarke and stands over 190 metres high.

Other must-visit places include the enormous and scenic Forest Park; the one-of-a-kind City Museum, constructed using unique found objects; and the National Blues Museum, which honours the city’s local blues heroes including legendary blues musician Chuck Berry.

Missouri

Situated in midwestern America, with the Mississippi River forming its eastern border, Missouri is an extensive state, which is widely considered to be a tourist highlight of the Great Plains regions. It offers travellers a rich mix of natural beauty, historic charm, and classic Americana. For those tracing the legendary Route 66, the state presents some of the most memorable stops along the journey.

Carthage, with its stately courthouse and beautifully preserved Victorian architecture, is a highlight not to be missed. Travelers can visit the 66 Drive-In Theatre for a nostalgic movie night under the stars or explore the Precious Moments Chapel, famed for its whimsical artwork. Further along the route, Joplin charms visitors with vintage diners and vibrant murals, while Cuba—known as “Route 66 Mural City”—offers colorful glimpses into Missouri’s past.

Whether exploring small-town treasures or enjoying the rolling Ozark hills and scenic byways, Missouri captures the timeless magic of the open road and remains a true Route 66 favorite.

Kansas

Although Route 66 only passes through a small section of southeastern Kansas, this stretch is full of classic Americana charm. Travelers can explore quaint towns like Galena, with its vintage diners and nostalgic roadside attractions, and Baxter Springs, home to the Route 66 Visitor Center and historic murals celebrating the Mother Road.

Oklahoma

Situated in the midwestern region of the United States, the state of Oklahoma is known for its diverse and scenic landscapes characterised by beautiful hills, lakes, sand dunes, forests and the Great Plains.

Oklahoma City, the capital, is home to the National Cowboy and Western Heritage Museum, focused on the state’s pioneer history, and the Bricktown entertainment district, popular for dining and nightlife.

Visitors can look forward to experiencing the cowboy spirit by visiting heritage centres and ranches and by horse riding or even spending the night in a traditional tipi.

Other attractions include Little Sahara State Park, Lake Tenkiller, and the Talimena National scenic byway.

Not-to-be-missed is the Wichita Mountains Wildlife Refuge, home to buffalo, elk and deer, and Route 66, comprised of over 650 kilometres of iconic road - ideal for a classic American road trip.

Amarillo, Texas

Surrounded by endless grassland prairies and dramatic red sandstone cliffs, Amarillo is both the largest city and the cultural and commercial capital of the Texas Panhandle.

As the gateway to Palo Duro Canyon State Park, the city also serves as a mecca for outdoor enthusiasts who flock here to take advantage of the countless hiking, camping, mountain biking, ziplining, horseback riding, and wildlife viewing opportunities on offer.

Amarillo’s Route 66 Historic District is a delight to explore as it is dotted with a variety of restaurants, cafes, clubs and antique stores, many of which occupy beautiful old art deco and Spanish Revival buildings.

Other popular attractions include the Cadillac Ranch, an art installation constructed using numerous graffiti-decorated cars and the Jack Sisemore Traveland RV Museum, featuring an impressive collection of vintage recreational vehicles.

View Itinerary in Detail

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All of our USA Holidays are completely tailor made and we can put together any kind of itinerary to suit your interests and budget.

We have many other options so if you have a particular hotel in mind just let us know and we'll put together a price and itinerary for you.