NO ONE-WAY DROP OFF FEES!* Saving over $500!

Delve into the expansive American countryside as you travel across eight great states during your exciting fly-drive adventure where you’ll explore not one, but two iconic road trips in one memorable holiday.

Starting in Chicago, you’ll follow the Mother Road west. Enjoy taking in the sights of modern infrastructure, preserved Route 66 memorabilia and impressive landscapes whilst capturing the culture and diversity of the country. During your cross-country exploration you’ll sleep in a Wigwam, visit the mighty Grand Canyon and experience the bright lights of Las Vegas.

After a quick switch of cars in Los Angeles, you’ll journey along one of the world’s most scenic routes that leads to San Francisco. Swing by charming surf towns, travel through the winelands and discover romantic hideaways as you explore California’s rugged Pacific Coastline.


Chicago – Springfield – Saint Louis –Springfield – Oklahoma City – Amarillo – Albuquerque – Gallup – Holbrook – Grand Canyon – Las Vegas – Los Angeles – Santa Barbara – Cambria – Monterey – San Francisco 


*Please Note: The 'no one-way drop off fee' offer only applies for car hire collected from Chicago O'Hare Airport and dropped off at Los Angeles Airport on selected dates in 2017/18 and a second car being collected at Los Angeles Airport and dropped off at San Francisco Airport for this itinerary. Please ask for full details. Subject to availability.

Day 1: UK – Chicago

Today you begin your journey by boarding your international flight to Chicago.

On arrival you will collect your hire car from the airport and drive to your centrally located hotel in Downtown Chicago.

The rest of the day is free for you to explore the city at your own leisure.

Accommodation in Chicago: The Drake Hotel (or similar)

Day 2: Chicago

We reckon the best way to scope out the architectural delights and iconic sights of Chicago is to join a hop-on, hop-off city tour. You’ll get the chance to stop off and explore the main attractions, such as the Millennium Park, Art Institute of Chicago, Magnificent Mile and the Navy Pier.

Chicago has a renowned culinary scene, so head down to Restaurant Row or West Loop and treat your taste buds to a delicious dinner this evening.

Accommodation in Chicago: The Drake Hotel (or similar)

Day 3: Chicago – Springfield, Illinois (205 miles)

Today you will set off on the first part of this iconic road trip - your Route 66 adventure begins here!

As you leave Chicago behind, you will start to notice Route 66 icons and signs popping up along the roadside. Travel through hometown neighbourhoods and stop off to enjoy classic Route 66 points of interest including the Route 66 Raceway and the Gemini Giant.

Once you’ve arrived in Springfield, head into the heart of town to walk in the footsteps of President Abraham Lincoln and discover authentic Route 66 landmarks. Stop by Shea’s Gas Station, watch a movie at the Route 66 Drive-in Theatre and try a hot dog on a stick at the Cozy Dog Drive In.

Accommodation in Springfield: Ramada Springfield North (or similar)

Day 4: Springfield – Saint Louis (97 miles)

Today you will hop back into your car and drive onwards to the banks of the Mississippi River where you’ll find Saint Louis.

Spend some time admiring the Gateway Arch, an engineering marvel, either from the ground or up in the air, if you choose to take a ride to the top. Check out what’s going on in Forest Park and when you’re feeling peckish, swing by Ted Drewes to enjoy a bite of Frozen Custard - an iconic stop along Route 66 for those seeking a tasty break.

Accommodation in Saint Louis: Hampton Inn Gateway Arch (or similar)

Day 5: Saint Louis – Springfield, Missouri (215 miles)

Today you will continue your drive through landlocked Missouri, passing the rolling hills of the Ozark Mountains until you reach Springfield.

When you arrive, check in and admire the nostalgic design of this award-winning hotel. Complete with an original gas station that, at one point, was used by many who travelled along Route 66 as well as classic Cadillacs parked outside; enjoy the modern amenities whilst feeling like you are stepping back in time.

Later on you might choose to visit Meramec Caverns and discover the cave system that spans 4.6 miles underground, or take a stroll through Downtown Springfield and soak up the atmosphere of this friendly town.

Accommodation in Springfield: Best Western Route 66 Rail Haven (or similar)

Day 6: Springfield – Oklahoma City (286 miles)

Today you will leave Missouri behind you as you drive full steam ahead into the dusty dry Southwest countryside through small towns and farmlands. Make a pit stop en route to Oklahoma City at Ed Galloway’s Totem Park Pole to stretch your legs and have a wander around the impressive selection of folk art.

Known for its cowboy heritage and Native American influences, Oklahoma City offers a variety of cultural activities for you to enjoy that play tribute to its Western past. This afternoon you might choose to visit the National Cowboy & Western Heritage Museum and galleries showcasing Western art.

Accommodation in Oklahoma City: Best Western Plus Broadway Inn & Suites (or similar)

Day 7: Oklahoma City – Amarillo (260 miles)

Today you will travel right into the heart of Cowboy country as you cruise through the ‘Lone Star State’, Amarillo bound.

Enjoy staying at the Big Texan Motel, an iconic spot along the Mother Road and right next door to the Big Texan Steak ranch, so you haven’t got far to walk back if you dare try the ‘Texas King’ steak eating challenge!

Accommodation in Amarillo: Big Texan Motel (or similar)

Day 8: Amarillo – Albuquerque (287 miles)

Shortly after leaving Amarillo today you will come across the legendary ‘Cadillac Ranch’, an artistic endeavour that’s now a quirky Route 66 stop-off point.

Once you arrive in Albuquerque, step outside into the high desert air and start uncovering the town’s deep rooted heritage and historic delights. You might choose to enjoy the self-guided Route 66 Tour this afternoon that takes you past the neon Route 66 lights in Nob Hill, all the way through to the Old Town.  

Accommodation in Albuquerque: Doubletree by Hilton Hotel Albuquerque (or similar)

Day 9: Albuquerque – Gallup (140 miles)

Next stop on the route is Gallup, a quiet town that hasn’t changed much since the 1950s but is brimming with Route 66 memorabilia and native American history.

Enjoy spending the night resting your head where a long list of famous movie stars have before you when El Rancho was an iconic base for movie productions.  

Accommodation in Gallup: El Rancho Hotel (or similar)

Day 10: Gallup – Holbrook (97 miles)

Today you will drive through the Petrified Forest until you reach the Wild West town of Holbrook.

After checking into your Wigwam accommodation, the day is free for you to take a tour of a working ranch, visit ancient Indian rock art sites or attend a rodeo.

Accommodation in Holbrook: Wigwam Motel Holbrook (or similar)

Day 11: Holbrook – Grand Canyon (180 miles)

On your way to the Grand Canyon today, make a stop at the fascinating 550 feet deep Meteor Crater that hit the earth approximately 50,000 years ago.

Once you arrive at the South Rim, take your pick of the various viewing platforms for your viewing pleasure as you take in the magnificent sights of the striking vistas of the mighty Grand Canyon.

There are plenty of hiking and biking trails for you to follow, or enjoy spending time in the Grand Canyon village.

Accommodation in Grand Canyon: Best Western Premier Squire Inn Grand Canyon (or similar)

Day 12: Grand Canyon – Las Vegas (280 miles)

Today you will drive along seemingly endless desert roads until the bright lights of Las Vegas shine as bright as a beacon ahead of you.

After checking into your hotel, delve into the lavish mix of glitz and glamour along the Vegas strip; dip into the mega hotels, stop by the casinos and check into a show. Anything goes in Las Vegas and the world is your oyster here.

Accommodation in Las Vegas: Luxor (or similar)

Day 13: Las Vegas

Another day, another dollar. Enjoy continuing your exploration of the ever-changing faces of Vegas.

Accommodation in Las Vegas: Luxor (or similar)

Day 14: Las Vegas – Los Angeles (270 miles)

Wave goodbye to Vegas as it shrinks behind you in the distance as you drive on through the Mojave Desert toward the ‘City of Angels’.

When you arrive into Los Angeles, spend the day exploring the Hollywood Walk of Fame, stop by lively Venice Beach or head to the Griffith Observatory to view the iconic Hollywood sign.

Accommodation in Los Angeles: Luxe Sunset Boulevard Hotel (or similar)

Day 15: Los Angeles

Spend today continuing to explore the beating heart of America’s film and television industry or travel to Santa Monica and visit the Pier to take a photo next to the sign that marks the end of the Mother Road.

Later on today you will travel to Los Angeles Airport to drop off your hire car and collect your next one, ready to start your Highway 1 adventure the following morning.

Accommodation in Los Angeles: Luxe Sunset Boulevard Hotel (or similar)

Day 16: Los Angeles – Santa Barbara (96 miles)

Today marks the start of your second memorable road trip; from one of America’s greatest cities to another, over the next few days you will travel along California’s scenic Pacific coast to San Francisco, arguably one of the most beautiful routes in the world.

Head north on Route 101 until you reach picture perfect Santa Barbara, nestled between the Santa Ynez Mountains and the clear blue Pacific Ocean. This sophisticated hot-spot is home to streets lined with excellent bars, boutique shops, chic restaurants and perfect weather; it’s clear why this Southern Californian town is affectionately known as America’s Riviera.

Take a stroll and go for a shop along State Street, join the Urban Wine Trail Tour or relax on the endless stretch of idyllic beaches and soak up some Californian sun. Head down to the waterfront this evening to enjoy some fresh shellfish and admire the beautiful views across the bay as the sun softly sets.

Accommodation in Santa Barbara: Ramada Santa Barbara (or similar)

Day 17: Santa Barbara – Cambria (128 miles)

Today you will continue your journey along Highway 101 to the seaside village retreat of Cambria. En route you might choose to stop off at the Danish village of Solvang or head to Pismo Beach to catch some waves.

When you arrive at Cambria, visit the windswept coast or take a tour of the historic lighthouse. This cosy slice of paradise is the perfect spot to enjoy an overnight stay.

Accommodation in Cambria: Cambria Pines Lodge (or similar)

Day 18: Cambria – Monterey & Carmel (143 miles)

Shortly after leaving Cambria you will reach San Simeon. You might wish to stop here and make a visit to Moonstone beach to watch the Sea Otters basking in the sun before continuing your drive along the winding coastal route.

The rugged coastal route between San Simeon and Monterey is regarded one of the most scenically beautiful drives in the world, so sit back and enjoy watching spectacular landscapes unfold in front of you. Make time to see the McWay Falls that plummets into the ocean and stop to take a photo of the iconic Bixby Bridge. 

Stop by the quaint and fairy-tale like village of Carmel-by-the-Sea, before reaching lively Monterey where you will spend the night. Head to Cannery Row for a spot of wine tasting or Fisherman’s Wharf to take your pick of the fresh seafood restaurants.

Accommodation in Monterey: Bay Park Hotel (or similar)

Day 19: Monterey & Carmel – San Francisco (123 miles)

This may be the last stretch of road on your double road trip through America, but it won’t fail to disappoint; it’s every bit as impressive as the Big Sur. Breeze past rolling hills, charming towns and rocky shores as you drive through the Santa Cruz mountain range to San Francisco.

When you arrive, it’s time to start exploring the great sights of San Francisco, once the fog lifts of course.  

Accommodation in San Francisco: Hotel Cartwright Union Square (or similar)

Day 20: San Francisco

Fisherman’s Warf, Alcatraz, Lombard Street, Coit Tower and the Golden Gate Bridge; take your pick and start exploring the main sights during your last full day in the fun and fabulous Frisco!

 Accommodation in San Francisco: Hotel Cartwright Union Square (or similar)

Day 21: San Francisco – Departure

Enjoy spending this morning in San Francisco at your own leisure.

Later on you will drive to San Francisco International Airport where you will drop off your hire car and board your international flight back to the UK.

Day 22: Overnight flight – Arrival

Today you will arrive back into the UK, where you will continue your journey home.


Our selection of hotels has been handpicked and comes recommended by our local representatives for their location, service and facilities. We do however have many other accommodation options covering various star ratings, dining options and budgets. We'd be delighted to provide you with a personalised quote that covers your exact requirements. Call one of our specialists or use our enquiry form for a quotation.

Tailor Make This Holiday

This holiday can be completely tailor made to suit your wishes and requirements.

You can...

  •  Extend or shorten the itinerary
  •  Add extra stops in
  •  Cut out some days
  •  Reorder the itinerary
  •  Stay in alternative accommodation
  •  Fly from a different airport
  •  Add in extra adventures and experiences

This is what our tailor made service is all about.

Just contact us to discuss your ideas with one of our friendly travel experts.

 01622 608 265orEnquire Online

This is a suggested self-drive itinerary, which our dedicated travel team can tailor to suit your exact requirements. If you would prefer a larger vehicle or a convertible car, just let us know and we can provide you with a quotation based on your preferred option.

Prices start from £2,489.00 per person based on two adults sharing a twin/double room.

Price includes:

  • International flights from London to Chicago/ San Francisco to London in Economy Class
  • UK & US Airport Taxes
  • Total 20 nights in 3-4* hotel accommodation, room only basis
  • Car Hire, inclusive of one way drop off fee, taxes and charges - saving you up to $500!

Price excludes:

  • Any personal expenses (meals, room service, gratuities, laundry etc.)
  • Petrol
  • GPS Unit
  • Attraction/ entrance tickets
  • Travel insurance
  • Any other services not listed as ‘inclusive’

How to book with Medway Leisure Travel

1 Contact our holiday experts

For further details regarding this holiday, call our friendly team of holiday experts on 01622 608 265 or simply email us by using our Enquiry Form

2 Planning your holiday

Our passionate and experienced travel team look forward to discussing and planning your holiday with you: offering advice and providing suggestions to help you find the perfect trip.

3 Refine your itinerary

Your dedicated holiday expert will create a detailed itinerary for you, which we will then send to you via email. We can then refine this together, until we have created your perfect holiday.

4 Complete your booking

Once you are happy with all your travel arrangements, we can complete your booking for you by collecting your deposit.

5 Keep in touch

If you have any questions or queries after completing your booking, our team of holiday experts and aftersales consultants are available to assist you on
01622 608 265.

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What We Love

How this exciting itinerary combines not one, but two great American Road trips in one memorable holiday!

Blog Post

Our Top Picks of USA’s great Road Trips!

  21 June 2017
  Zoe Tucker

The USA is one of the world’s greatest countries for road trip adventures. Stock up your car, wind the windows down, slip on your shades and listen to your carefully created playlist as you hit the wide open roads. ...

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  •  Book with confidence – we are members of ABTA and holders of ATOL and IATA licences

All of our holidays can be tailor made to suit you and your budget. Let our team of experts inspire you with their suggestions for your next holiday.

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