Bespoke Tour Quote
Route 66 Motorcycle Tour
Route 66
Motorcycle Tour
The Mother Road, end to end — 2,807 miles from Lake Michigan to the Pacific on a Harley Street Glide. Fourteen riding days on a fully escorted group tour, with a welcome dinner in Chicago, a farewell dinner in LA, and a free day in Santa Fe halfway through.
Day by Day
Monday 6 September — Manchester at breakfast, Chicago by lunch. Two warm-up nights in the city, then fourteen days west on the Mother Road.
Manchester → London → Chicago
British Airways BA1381 from Manchester at 08:00, into Heathrow at 09:15. Connect onto BA295 at 11:10 for the eight-hour-forty hop west, into Chicago O’Hare at 13:50 local. Airport transfer to the Hilton isn’t included — budget for an Uber or town car.
A free day in Chicago
A free day in Chicago before the tour begins. The Hilton is on South Michigan Avenue, overlooking Grant Park and Lake Michigan.
Chicago, IL — Arrival
Welcome to the Windy City, where your Route 66 journey begins! Chicago’s stunning skyline rises majestically along Lake Michigan’s shores, setting the stage for your epic adventure. This Great Lakes metropolis pulses with world-class museums, acclaimed restaurants, and vibrant blues clubs that honor the city’s rich musical heritage. Tonight at the tour hotel, meet your fellow riders and guides for an orientation meeting followed by a Welcome Dinner. Rest up — tomorrow you hit the Mother Road.
Chicago, IL → Springfield, IL
Pick up your motorcycle at the Chicago rental depot, where Route 66 officially starts its 2,807-mile stretch to the Pacific. Head south on the historic Pontiac Trail through Joliet and into the heartland of Illinois. Make a stop at the Route 66 Museum in Pontiac to absorb the road’s rich history before continuing your ride. Feel the rhythm of the road as you complete your first stretch of this legendary highway — just the beginning of your Route 66 adventure.
Springfield, IL → St. Louis, MO
Off to St. Louis! Cruise the 2-lane sections of Route 66 through Illinois’ heartland, where cornfields stretch to the horizon and small towns showcase quintessential Americana. Take in views of the historic Chain of Rocks Bridge — the original Route 66 river crossing — as you approach St. Louis, the “Gateway to the West.” This shorter riding day leaves time to explore the city’s famous landmarks and sample its renowned BBQ and live music scene along the banks of the Mississippi.
St. Louis, MO → Joplin, MO
Rise early for a glimpse of the iconic St. Louis Arch before leaving the city behind. Missouri’s rolling hills provide the perfect backdrop as you lean into the curves of Route 66. Stop at the World’s Largest Rocking Chair in Fanning and navigate the twisting roads of Devil’s Elbow — both quintessential Route 66 photo opportunities. End your day in Joplin, a resilient city with powerful stories of survival following the devastating 2011 tornado. Connect with locals at dinner to hear firsthand accounts of this historic event.
Joplin, MO → Oklahoma City, OK
Ride west from Joplin through Oklahoma’s rolling hills and horse country. Pass through Miami, Claremore, and Catoosa — home to the quirky Blue Whale roadside attraction — before reaching Tulsa. Your route crosses lands of the Choctaw, Chickasaw, Seminole, Creek, and Cherokee Nations, where Native American history runs deep. These territories, once deemed “unusable” by the Federal Government in the 1830s, became reservation lands following forced relocations. End your day in Oklahoma City, considered the heart of Route 66. Spend your evening exploring Bricktown, the city’s vibrant entertainment district filled with restaurants, bars, and shops.
Oklahoma City, OK → Amarillo, TX
Oklahoma’s oldest stretches of Route 66 await this morning, taking you through lands once roamed by vast buffalo herds. Cross the historic Chisholm Trail through Yukon and El Reno, where legendary cattle drives moved thousands of longhorns north from Texas in the 1860s. Stop at the Route 66 Museum in Clinton before crossing into the Texas Panhandle, where the Great Plains stretch toward the horizon. Arrive in Amarillo with time for an optional visit to the legendary Big Texan Steakhouse — home to some of the best steaks in Texas and the famous 72-ounce steak challenge.
Amarillo, TX → Santa Fe, NM
Begin your day at the iconic Cadillac Ranch before reaching Adrian, Texas — the official midpoint of Route 66. Stop in the ghost town of Glen Rio to stand with one foot in Texas and the other in New Mexico. Cross into “The Land of Enchantment” and enter former Comanche territory. The landscape changes dramatically — mesas rise from the plains, pine trees appear, and the air thins as you climb into the High Plains. End your journey in Santa Fe, one of America’s oldest and most beautiful cities, where you’ll spend two nights immersed in its unique blend of Native American, Spanish, and Western cultures.
Santa Fe, NM — Free Day
Take a well-deserved break in Santa Fe, a 400-year-old city where Southwestern culture comes alive through distinctive architecture, cuisine, and art. Choose your own adventure today: ride to the ancient Native American pueblo of Taos, drift above the Rio Grande Valley in a hot air balloon, or explore the surrounding mountains on horseback. This free day offers a perfect opportunity to immerse yourself in Santa Fe’s rich heritage, vibrant arts scene, and renowned culinary traditions.
Santa Fe, NM → Gallup, NM
Head south to Albuquerque, New Mexico’s largest city and vital crossroads where the Rio Grande meets historic trade routes. After crossing the Rio Grande, the landscape opens into the striking Navajo wilderness. Ride past dramatic mesas and bluffs through Laguna and Grants, with Cibola National Forest creating a stunning backdrop. Your day ends in Gallup, a classic Route 66 railroad town with deep Native American heritage. This popular stop for riders from around the world offers authentic Southwestern hospitality and a true taste of the old Route 66.
Gallup, NM → Grand Canyon, AZ
Cross into Arizona today and explore Petrified Forest National Park, where ancient fossilized trees reveal a prehistoric landscape sculpted by time and erosion. Continue to iconic Route 66 landmarks including the distinctive Wigwam Hotel in Holbrook and the famous corner in Winslow, Arizona immortalized by the Eagles. While most tours stop in Flagstaff or Williams, we push on to lodge just one mile from the Grand Canyon’s South Rim. End your day with a sunset view over one of the world’s most spectacular natural wonders.
Grand Canyon, AZ → Laughlin, AZ
Start your day with a helicopter flight over the Grand Canyon’s South Rim for an unforgettable aerial perspective. Rejoin Route 66 in Williams and continue through a string of iconic highway towns — Seligman, Hackberry, and Kingman — each preserving a unique slice of Mother Road history. Wind through the historic mining town of Oatman before descending to Laughlin, where your riverside hotel awaits on the banks of the Colorado River.
Laughlin, AZ → Las Vegas, NV
Take a short detour from Route 66 for a taste of Las Vegas excitement. The morning ride crosses the stark beauty of the Mojave Desert and the engineering marvel of Hoover Dam. Arrive in Las Vegas with time to experience the city’s legendary entertainment, dining, and nightlife. This brief visit offers a vibrant contrast to the small towns of Route 66. Rest up if you can — tomorrow we’ll return to where we left the Mother Road and continue our westward journey.
Las Vegas, NV → Victorville, CA
Enter California — the final state of your Route 66 adventure. Cross the magnificent Mojave Desert, where dramatic landscapes of volcanic rock, sand, Joshua trees, and cactus create an otherworldly backdrop for your ride. Stop in the tiny outposts of Amboy and Ludlow, historic “waystations” that once provided crucial services to early Route 66 travelers making the challenging desert crossing. Tonight marks your final evening on the Mother Road, a perfect opportunity to share stories and celebrate.
Victorville, CA → Los Angeles, CA
Your final day begins with one of Southern California’s premier motorcycle experiences — 66 miles along the Angeles Crest Highway. Wind through Angeles National Forest, climbing to over 7,500 feet before descending into the Los Angeles Basin. Reach the iconic Santa Monica Pier and the historic “End of the Trail” sign — a triumphant finale to your 2,807-mile journey across America. Tonight, celebrate your adventure and new friendships at our special Farewell Dinner.
Los Angeles → London
Check out of the tour hotel in the morning; transfer out to LAX is on you (Uber or a hotel-arranged town car; the airport is about 15 minutes from Santa Monica, 40 from downtown). British Airways BA282 at 15:45 — the long one back, ten and a half hours over the pole, red-eye into Heathrow early the next morning.
London → Manchester
Land at Heathrow 10:15, through the border, pick up the Manchester connection — BA1364 at 12:05, home at 13:10 Thursday afternoon.
Route 66 Escorted Motorcycle Tour
Fourteen days on a Harley Street Glide — the inclusions, in detail.
Harley Street Glide — unlimited miles
Your bike for the fourteen days is a Harley-Davidson Street Glide — the touring Harley, with the batwing fairing, hard panniers and the Boom! Box audio system. Unlimited miles, so there’s no clock watching if you want to loop off for a photo or a diner.
All the on-bike kit is included — DOT-approved helmets for rider and pillion, two cable locks and a disc lock, and a secure VIP Zero deposit waiver so your card doesn’t get a hold on it when you collect.
Everyone on the tour carries the same cover: Supplemental Liability Insurance, Personal Accident & Effects.
Where You Stay, How You Travel
Hilton Chicago — your first two nights
A historic hotel on South Michigan Avenue, overlooking Grant Park and Lake Michigan — the kind of building that still has a doorman and a brass elevator. The Hilton sits close to The Chicago Loop and is ideally placed for Soldier Field, the Shedd Aquarium, Adler Planetarium and the Buckingham Fountain. Spacious king rooms with blackout curtains, Hilton’s signature Serenity Beds, flat-screen TVs and coffee makers.
Room: King Room, Room Only (breakfast not included — the hotel has 720 South Bar & Grill downstairs, or you’re a short walk from any coffee shop in the Loop). Nights 1 and 2 of the trip, Monday 6 and Tuesday 7 September. A $29.73 resort fee is payable locally at checkout.
What’s Included
Included in your price
- British Airways flights, Manchester ↔ London Heathrow ↔ Chicago O’Hare / Los Angeles LAX — all four sectors, economy, 23kg per person checked
- Two nights at the Hilton Chicago (South Michigan Avenue), King Room, Room Only
- The 14-night escorted motorcycle tour, Chicago to Los Angeles — Harley Street Glide with unlimited miles
- Fourteen tour hotel nights on the route (operator’s selection)
- Welcome Dinner in Chicago on tour Day 1, Farewell Dinner in Los Angeles on tour Day 14
- Grand Canyon helicopter flight over the South Rim on tour Day 11
- DOT helmets for rider and pillion, cable locks and disc lock, VIP Zero deposit waiver
- Supplemental Liability Insurance and Personal Accident & Effects cover
- Fuel on all riding days — covered by the tour
- Tour guide and mechanic riding with the group, two support vehicles for luggage
- Full ATOL financial protection — see legal below
Not included — allow for these
- Airport transfers at both ends (Chicago ORD → hotel, and tour hotel LA → LAX) — budget ~$60–80 each way for an Uber or a town car
- Resort fee at the Hilton Chicago — $29.73 per night, paid at checkout (~£45 total for the two nights)
- Breakfast and most dinners outside the Welcome and Farewell dinners
Your Price
For one rider, on a Harley Street Glide.
Flights, hotel, escorted motorcycle tour and all inclusions
How payment works on this one
£250 deposit secures your place on the tour and the Chicago hotel. Full balance of £12,067.90 is due on 24 May 2027, 14 weeks before departure.
The escorted tour has a limited group size and sells out for the September departure a long way in advance, so the earlier the deposit lands, the better your chance of the exact dates and the Street Glide.
Hotel & tour booking conditions. The motorcycle tour and the Hilton Chicago both carry name-change and amendment restrictions — once ticketed, name changes and date amendments need the operator and the hotel to approve and may not be possible. Cancellation terms tighten as the trip approaches; the full schedule is in the terms link below.
Your money is protected. Road Trip Co is part of Travelosophers (Travel Philosophy Ltd). This holiday is arranged with a specialist US tour operator, whose booking conditions apply. Paying for your holiday confirms you’ve read and accepted them. Prices and availability are not guaranteed until the booking is confirmed, and local fees and taxes payable in resort can change without notice.