ROUTE 66 • OCT 3–17, 2026
Route 66 Tour 2026 — The Mother Road, Your Way
15 days across 8 American states.
4,872 km from Chicago to Santa Monica on the most legendary road in the world.
Route 66 is more than a road — it’s a piece of American mythology. Born in 1926 to connect Chicago to Santa Monica, it crossed eight states, transformed mid-century America, and inspired countless songs, films, and dreams. Decommissioned in 1985, much of it survives as Historic Route 66 — a patchwork of original alignments, vintage diners, neon-lit motels, and ghost towns that you can ride end to end.
15 days, 4,872 km / 3,028 mi, eight states (IL, MO, OK, TX, NM, AZ, NV, CA), and the freedom to choose your machine. Harley-Davidson Touring 1800cc for the classic American chrome experience, or BMW R1300GS for adventure-touring comfort. UpSerra coordinates everything: rental, hotels, support vehicle, bilingual tour leader (Portuguese / English), professional photo coverage.
Iconic stops along the way: Cadillac Ranch in Amarillo, Santa Fe adobe streets, Monument Valley red sandstone, Grand Canyon South Rim, Las Vegas, Sequoia National Park, and the Santa Monica Pier at the End of the Trail. This is the version of the Mother Road that international tour leaders deliver — small group, full curation, intentional pace. American road trip with UpSerra style.
IN MOTION
Watch the institutional video
UpSerra institutional video — the spirit of the operation, the team, and what we deliver. This is the first edition of Route 66; in October we’ll come back with our own footage.
More videos on @upserra YouTube channel →
THE ROUTE
Chicago → Grand Canyon → Las Vegas → Sequoia → Santa Monica
Day-by-day itinerary
DAY 01 · SAT OCT 3 · CHICAGO
Arrival in Chicago
Welcome at the hotel. Bike handover (Harley-Davidson Touring 1800cc OR BMW R1300GS, your choice at booking). Technical briefing with the UpSerra team, equipment check, and luggage adjustment. Welcome dinner — classic American diner, burger, cold beer.
DAY 02 · SUN OCT 4 · 326 KM
Chicago → Springfield, IL
Mile zero of Route 66. Departure from the Begin of Route 66 sign in Chicago, crossing Illinois cornfields and historic small towns. Overnight in Springfield, Lincoln’s hometown and the city where he built his political career before the White House.
DAY 03 · MON OCT 5 · 170 KM
Springfield → St. Louis
Short stretch to ease in. Crossing the Mississippi River into St. Louis (Missouri), with the iconic Gateway Arch framing sunset. Overnight in the city that was the gateway to the American West in the 19th century.
DAY 04 · TUE OCT 6 · 630 KM
St. Louis → Tulsa
Classic Route 66 stretch with stops at neon diners, vintage gas stations from the 50s, and traditional towns that lived off the road’s traffic before the interstate era. Crossing Missouri and a short slice of Kansas (mandatory on this route). Overnight in Tulsa, Oklahoma.
DAY 05 · WED OCT 7 · 588 KM · CADILLAC RANCH
Tulsa → Amarillo (TX)
The infinite horizons of Texas start here. Mandatory stop at the Cadillac Ranch — art installation with 10 Cadillacs buried nose-down in the desert, covered in graffiti (you can bring a spray can and leave your mark). Arrival in Amarillo, capital of the Texas Panhandle.
DAY 06 · THU OCT 8 · 448 KM
Amarillo → Santa Fe (NM)
Entry into New Mexico and the landscapes of the American Southwest. Santa Fe is one of the oldest cities in the US (founded 1610), with preserved Spanish colonial architecture (adobe buildings), Native American art galleries, and authentic Tex-Mex gastronomy. Historic district registered with UNESCO.
DAY 07 · FRI OCT 9 · 611 KM · MONUMENT VALLEY
Santa Fe → Kayenta
Day of the iconic Western landscapes. Passage by Shiprock (sacred Navajo rock formation) and arrival at Monument Valley — red sandstone buttes that became the calling card of John Ford westerns and Forrest Gump. Overnight in Kayenta, on the Navajo reservation.
DAY 08 · SAT OCT 10 · 345 KM · GRAND CANYON
Kayenta → Williams (Grand Canyon)
Crossing of Grand Canyon National Park — one of the most imposing landscapes on the planet. Viewpoints on the South Rim, colors shifting from red to purple depending on the hour. Overnight in Williams, the village that reinvented itself as the capital of Route 66 tourism with themed bars and the historic train station.
DAY 09 · SUN OCT 11 · 518 KM · SELIGMAN · OATMAN · HOOVER DAM
Williams → Las Vegas
Probably the most cinematic day of the tour. Route 66 nostalgia in Seligman (the village that inspired Pixar’s Cars), stop at the Hackberry General Store, technical challenge of the Sitgreaves Pass (winding mountain road) descending to Oatman — mining town with wild burros walking freely down the main street. Crossing of the Hoover Dam and arrival under the lights of the Las Vegas Strip.
DAY 10 · MON OCT 12 · LAS VEGAS · FREE
Free day in Las Vegas
Rest day in the city that never sleeps. Cirque du Soleil show, premium dinner, iconic Strip casinos (Bellagio, Caesars, MGM), pool party, or day trip to Red Rock Canyon or Valley of Fire. Each rider lives their own Vegas.
DAY 11 · TUE OCT 13 · 521 KM · MOJAVE
Las Vegas → Kernville
Crossing of the Mojave Desert (alternate route to Death Valley to avoid extreme October temperatures). Approach to Sequoia National Park, crossing the Kern River Canyon with its red gorges. Overnight in Kernville, mountain village with outdoorsy vibe.
DAY 12 · WED OCT 14 · 363 KM · SEQUOIA NP
Kernville → Fresno
Crossing the Sequoia National Park on the most cinematic roads in the park: Kern River Road, Mountain Highway 99, Tunnel Rock, Tunnel Log, and stop at the General Sherman Tree — the largest living tree on the planet by volume (275 ft / 84 m tall, 102 ft / 31 m circumference). Descent to Fresno.
DAY 13 · THU OCT 15 · 352 KM · END OF THE TRAIL
Fresno → Santa Monica
The day to close the loop. Descent through inland California to the Santa Monica Pier, mandatory photo under the “End of the Trail” sign — the point where Route 66 ends, on the Pacific. Mile 2,448. Closing toast with the team.
DAY 14 · FRI OCT 16 · SANTA MONICA · FREE
Free day in LA
Day to explore Los Angeles: Hollywood, Beverly Hills, Venice Beach, Walk of Fame, Griffith Observatory. Or just stay on the Pacific watching sunset on the beach. Or shopping at the outlets. Or rest — you just rode across a continent.
DAY 15 · SAT OCT 17 · FINISH
Bike return · Flight home
Bike return at the LA rental partner. Transfer to LAX airport and flight home. For those who want to extend, UpSerra suggests options: extra night in Las Vegas, San Francisco to the north, or a Cancún stopover on the way back.
EXPEDITION MEMORIES
Route 66 in pictures
Photos from previous editions along the way — Chicago, Monument Valley, Las Vegas, Santa Monica. To give you a sense of what’s waiting in October.
More on Instagram @upserra_ →
ROUTE 66 EXPERIENCE
The Mother Road, your way
Route 66 has existed since 1926 — diners, vintage motels, 1950s gas stations still operating, towns frozen in time when the interstates were built and traffic moved elsewhere. This tour preserves that rhythm, with no shortcuts. You choose the bike: Harley-Davidson Touring for the classic American experience, or BMW R1300GS for a more upright riding position and dual-sport versatility.
It’s eight states in fifteen days: Illinois (urban), Missouri (Mississippi), Oklahoma (cowboy country), Texas (infinite horizon), New Mexico (Spanish colonial), Arizona (Grand Canyon, Monument Valley), Nevada (Las Vegas, Hoover Dam), and California (Sequoia, Pacific). Almost 5,000 km / 3,100 mi — and each state with its own absolutely distinct identity.
Full UpSerra logistics: hand-picked hotels, bilingual tour leader, mechanical support vehicle, professional photo coverage. The rental partner provides premium bikes in both options — Harley-Davidson Touring up to 1800cc (Road King, Heritage Classic, Street Glide, Road Glide, or Electra Glide) or BMW R1300GS — depending on rider’s choice and availability at booking.
What’s Included
- Motorcycle rental for 15 days — your choice of Harley-Davidson Touring 1800cc OR BMW R1300GS, with basic insurance included
- UpSerra bilingual tour leader (Portuguese / English) for all 15 days
- Mechanical and logistical support vehicle
- 14 nights of selected accommodation (Chicago, Springfield, St. Louis, Tulsa, Amarillo, Santa Fe, Kayenta, Williams, Las Vegas, Kernville, Fresno, Santa Monica)
- Technical briefing in Chicago + bike handover
- Professional photo and video coverage of the expedition
- Complete planning of route, historic stops, and logistics
- Pre-trip support (documentation, visa, equipment, flights)
Not Included
- International airfare to Chicago + from Los Angeles
- US visa or ESTA waiver (USD 21, online — depending on your country)
- Motorcycle fuel during the tour (~USD 600–900 across 4,872 km)
- Meals (breakfast included at hotels — high-quality American gastronomy along the way)
- Mandatory international travel insurance
- Park entrance fees (Grand Canyon, Sequoia, Monument Valley — ~USD 100–150 total)
- Las Vegas attractions (shows, casinos, premium restaurants)
- Personal expenses
You choose between Harley-Davidson Touring (Road King, Heritage Classic, Street Glide, Road Glide, or Electra Glide) or BMW R1300GS — depending on preference and availability. The earlier you confirm your spot, the more options. USD 2,000 hold placed on your credit card at pickup (released at return).
Requirements
Documentation (international riders)
- Passport valid for at least 6 months beyond return date
- For non-US citizens: ESTA visa waiver (online, USD 21) or B1/B2 visa, depending on your home country. UpSerra confirms requirements at booking
- Motorcycle license (Class M or Class A equivalent) — at least 1 year holding it. Rental partner accepts home country license; International Driving Permit (IDP) recommended, especially for non-US riders (issued by AAA in the US, AA in UK)
- International credit card with at least USD 2,000 available limit (bike security hold)
- Round-trip international flight to Chicago (arrival by Oct 3) + from Los Angeles (departure on or after Oct 17)
- Mandatory international travel insurance with motorcycle riding coverage and US medical (US healthcare is expensive — minimum USD 100,000 coverage recommended)
Other requirements
- Heavy-bike experience required (1000cc+): Harley Touring 1800cc weighs ~400 kg / 880 lb; BMW R1300GS ~250 kg / 550 lb. Comfort with weight at low speeds is essential. 5,000+ km on heavy-bike touring needed
- Riding gear: helmet (mandatory in Texas/California, recommended in all states), jacket with full protection, gloves, riding pants, boots, knee armor, rain shell
- Layered weather gear: October across 8 states ranges from 5°C / 41°F (Sequoia mornings) to 30°C / 86°F (Mojave afternoon). Layered system mandatory
- Vaccinations: none mandatory for US entry
RESERVE YOUR SPOT
Reserve your spot — Route 66 October 2026
Leave your details and our team will reach out on WhatsApp within 24 hours.
Prefer to talk first? Message us on WhatsApp →
Frequently Asked Questions
Harley or BMW — which should I choose?
Harley-Davidson Touring 1800cc is the classic American Route 66 experience — large, comfortable, chrome, the soundtrack of the road. ~400 kg / 880 lb, smooth highway cruiser. BMW R1300GS is the adventure-touring tool — lighter (~250 kg / 550 lb), more nimble, better for back-road exploration. Choose at booking. UpSerra coordinates either with the rental partner.
Do I need a visa for the US?
Depends on your country. ESTA visa waiver (USD 21, applied online): Canada, UK, EU, Australia, New Zealand, Brazil (recently joined), and ~40 others. B1/B2 visa: required for many other countries (consult US embassy). UpSerra confirms requirements at booking based on your nationality.
Is my motorcycle license valid in the US?
For US citizens: yes. For international riders: home country motorcycle license + International Driving Permit (IDP) recommended. Get IDP before traveling — issued by AAA in your home country.
What’s the weather like in October?
Variable across 8 states. Illinois/Missouri: 10–22°C / 50–72°F. Texas/New Mexico: 12–25°C / 54–77°F. Arizona/Nevada/California desert: 15–30°C / 59–86°F days, can drop to 5°C / 41°F at night in Sequoia/Sierra Nevada. Layered gear with rain shell mandatory. Rain unlikely.
How much fuel and food cost?
Fuel: ~USD 600–900 across 4,872 km (depending on Harley vs BMW). Meals: USD 30–60/day at Route 66 diners and roadside restaurants. Park fees: ~USD 100–150 (Grand Canyon $35, Sequoia $35, Monument Valley $20, etc.). Vegas optional. Budget USD 1,500–2,500 personal expenses for 15 days.
Best flights to Chicago?
Chicago has 2 main airports — O’Hare (ORD) and Midway (MDW). ORD has direct flights from most international hubs (London, Frankfurt, Tokyo, São Paulo, Mexico City, etc.). Plan to arrive 1–2 days early. Return flight from Los Angeles (LAX) on Day 15.
Is it tough for someone without big-bike experience?
Moderate level. Harley Touring weighs 350–400 kg (770–880 lb) and demands comfort with weight at low speeds. BMW R1300GS weighs ~250 kg (550 lb), lighter. 100% paved roads, comfortable averages (~325 km/day). Recommended for riders with heavy-bike (1000cc+) experience and at least one international motorcycle trip. Not ideal as a first international ride — start with Mendoza or Alps to build repertoire.
Where are bikes picked up and returned?
Pickup in Chicago on Day 1 (Oct 3), at the rental partner near the airport/hotel. Return in Los Angeles on Day 15 (Oct 17). Rental partner coordinates transfers between airport and your hotel. Riders flying internationally need to ensure flight to Chicago arrives by Oct 3 and from LA departs on or after Oct 17. UpSerra suggests compatible flight times.
How do I pay? What’s the deposit?
10% deposit at booking confirms your spot. Balance via international wire transfer in USD or credit card. Once you submit the booking form, our team contacts you on WhatsApp within 24 hours to handle the details.
Pricing
Per person, in USD. Motorcycle rental (Harley-Davidson Touring 1800cc OR BMW R1300GS) always included. International flight Brazil ↔ US on the rider.
| Package | Price (USD) |
|---|---|
| Rider — Twin Room (motorcycle included) | USD 8,000 |
| Rider — Single Room (motorcycle included) | USD 10,000 |
| Couple — Double Room (motorcycle included) | USD 11,000 |
Payment terms: 10% deposit at booking confirms your spot. Balance via international wire transfer (USD) or credit card. Talk to the UpSerra team on WhatsApp.
Limited spots.
Small group to preserve pace and full attention from the team.
Reserve your spot directly with our team.
“More than roads, we live experiences. More than destinations, we build friendships.”
@UPSERRA_ · OFFICIAL BMW MOTORRAD PARTNER