CANADA to KEY WEST
Chicago, Canada, New York to Key West
USA from North to South -
9 states - Approximately 5000 km
THE TOUR FOR THE TOUGHEST AND MOST ADVENTUROUS
Duration: 20 days - Driving days: 14 days
EXCLUSIVE TOUR!
There will be a maximum of ONE TOUR per year, with a maximum of 20 bikes.
THIS IS INCLUDED:
- Guided tours to various destinations around the world with our knowledgeable guides.
Daily itinerary
Preliminary Daily Itinerary:
15 days on the bike:
Day 1: Arrive in Chicago and check in at the hotel – In the evening, we’ll visit a blues pub (highly recommended)
Day 2: We’ll try to adjust to the time difference, so we’ll take a trip to the city center. There’s a lot to see, including the starting point of Route 66, skyscrapers, river cruises, parks, etc. (Signing papers for the bikes)
Day 3: Chicago to Milwaukee. We’ll travel to Milwaukee by bus and visit the Harley museum.
Day 4: Chicago to Detroit, the first day on the bike. We’ll pick up the bikes at 7:00 AM and plan to depart from Woodstock at 10:00 AM. This day will be a transit stage to Detroit, approximately 562 km. (Link to daily stage, this is not accurate but gives an idea of the route and destination)
Day 5: Detroit to Canada and Niagara Falls. We need to start early as we’ll end the day at Niagara Falls, approximately 404 km. (Link to daily stage, this is not accurate but gives an idea of the route and destination)
Day 6: Niagara Falls to Albany. A scenic drive with stops at some beautiful lakes, approximately 483 km. (Link to daily stage, this is not accurate but gives an idea of the route and destination)
Day 7: Albany to New York. We’ll drive through the countryside and stop at the Hudson River. There are many great roads for motorcycles, approximately 255 km. The day ends with a magnificent fireworks display as it’s the US Independence Day, a fantastic event with millions of spectators. (Link to daily stage, this is not accurate but gives an idea of the route and destination)
Day 8: 1 day in New York, two nights. We’ll take a tour of Manhattan. I highly recommend everyone to dine and enjoy the view from the top of One World Trade Center. There’s so much to see in this city that it would take many days, but we’ll get a taste of it.
Day 9: New York to Lancaster. We’ll start early in the morning (05:30 AM) to ride a bit through Manhattan before the traffic gets heavy. When we arrive in Lancaster, the plan is to visit the Amish market, approximately 300 km. (Link to daily stage, this is not accurate but gives an idea of the route and destination)
Day 10: Lancaster to Tappahannock. On this day, we plan to ride through Washington. If we’re lucky, we can take pictures with some of the famous buildings along with our bikes, approximately 390 km. (Link to daily stage, this is not accurate but gives an idea of the route and destination)
Day 11: Tappahannock to Kill Devil Hills. We’ll have different experiences and encounter various landscapes, trying to stop in some charming small towns along the way, approximately 326 km. (Link to daily stage, this is not accurate but gives an idea of the route and destination)
Day 12: Kill Devil Hills to Wilmington. We’ll have an exciting day as we enter the southern states with a rich history and culture. We’ll try to experience some of it, approximately 422 km. (Link to daily stage, this is not accurate but gives an idea of the route and destination)
Day 13: Wilmington to Savannah. A long and beautiful day on the bike. We’ll start to feel the heat more as we progress, approximately 482 km. (Link to daily stage, this is not accurate but gives an idea of the route and destination)
Day 14: Savannah to Daytona Beach. Enjoying nice roads with fewer alternative routes, approximately 367 km. (Link to daily stage, this is not accurate but gives an idea of the route and destination)
Day 15: Daytona Beach to Fort Myers. Now we’ll ride through Florida to the west coast, approximately 386 km. (Link to daily stage, this is not accurate but gives an idea of the route and destination)
Day 16: Fort Myers to Miami. We’ll ride through nature reserves and go on a swamp safari to see alligators, approximately 240 km. (Link to daily stage, this is not accurate but gives an idea of the route and destination)
Day 17: Miami to Key West. We’ll embark on a fantastic stretch with many bridges, both old and new. We’ll make stops for swimming. It will be a lovely afternoon and evening in Key West, approximately 210 km. (Link to daily stage, this is not accurate but gives an idea of the route and destination)
Day 18: Key West to Miami. We’ll ride another fantastic stretch with many bridges, both old and new. We’ll make stops for swimming, approximately 255 km. (Return the bikes) (Link to daily stage, this is not accurate but gives an idea of the route and destination)
Day 19: Miami. On this day, you can explore Miami, and in the afternoon, you can visit a shopping center. (Farewell dinner for those interested)
Day 20: Miami. Bus to the airport for the return flight home or further travels.
The itinerary may be subject to change before or during the trip due to various factors such as road work, accidents, etc. We should expect the daily stages to vary by +/- 10% from what we have provided.
We’ll do our best to find scenic roads for the motorcycles, where we can enjoy the diverse nature, culture, and historical areas of the United States. We’ll be riding from the northernmost point to the southernmost point. Some parts of the journey will include riding on interstates to reach our daily destinations on time.
We have included links to the daily stages, but they may not be accurate as they represent the fastest route. We’ll strive to take alternative roads that provide a better experience, allowing us to enjoy good motorcycle roads while getting closer to nature, local culture, and, most importantly, excellent motorcycle routes.
We are working on several places to visit along the way, but those will be a surprise.
For those who wish, you can extend your stay in Miami after the tour to relax on the beach.
This is a VERY LONG trip. Please contact us at post@route66usa.info with the subject “Coast-to-Coast USA” if you want to experience this tour.
This is the tour for the toughest and most adventurous riders. There will be only ONE tour annually, with a maximum of 20 bikes on each tour.
Overview map: The map shows the approximate route we’ll be riding.
THIS IS NOT INCLUDED:
- Airfare.
- Hotel/accommodation/lodging.
- Optional vehicle rental: car, motorcycle, or bus.
If you need assistance in booking the best hotels and flights, we can provide recommendations based on your preferences. If you require help with the actual booking process, our technical team can assist you for a fee of $200 per person.
Departure dates for 2025, 2026 and 2027
June 28th - July 17th
Satisfied customers
Price
Guided tour
$1966
FAQ
If you need assistance in booking the best hotels and flights, we can provide recommendations based on your preferences. If you require help with the actual booking process, our technical team can assist you for a fee of $200 per person.
All participants must apply for a visa to enter the United States before departure. This is done electronically through the following website: http://esta.cbp.dhs.gov/esta
If the ESTA visa is not issued through the online application, you will need to apply for an entry permit at the U.S. Embassy in your home country. It is your responsibility to obtain this well in advance of your trip, as well as travel insurance.
We have tours available from May through September each year. If you have the flexibility in terms of work and family, we recommend driving in May, June, or September. These months generally have more pleasant weather. July and August can be warmer.
The general rule is to bring one large bag or backpack per person, along with carry-on luggage. All luggage will be placed in the support vehicle, except for the items you need during the day (sunscreen, rain gear, camera, etc.). All motorcycles have storage space. We recommend bringing salt tablets from home due to the hot weather.
In such a case, the tour guide will ensure that you receive a “police report” regarding the damage caused, which will be handed over to the Harley dealer when returning the motorcycles. Your insurance company will take care of the rest.
If you lose your passport, you should report it to the police in the USA immediately. Your embassy or consulate will then issue an emergency passport, which usually involves a fee. An emergency passport can only be issued to individuals who can confirm their citizenship.
GOOD TO KNOW ON THE ROAD
- In the USA, you drive on the right side of the road.
- All distances are measured in miles. See conversions below.
- Traffic lights (red, yellow, green) are the same as in Europe.
- If the light is flashing yellow, be cautious when crossing the street.
- If the lights are flashing red, always stop before crossing the street.
- If you encounter an octagonal sign, come to a complete stop before proceeding.
- A yellow triangle means you must yield to oncoming traffic – you have the right of way.
- On roads with double yellow lines, it is prohibited to cross them for overtaking.
- On larger roads with multiple lanes in the same direction, traffic moves fastest in the leftmost lane. You are only allowed to overtake other vehicles on the left side.
- Speed limits vary from state to state.
- In most states, wearing a helmet and goggles is mandatory. You are responsible for this and drive at your own risk.
- It is prohibited to pass yellow school buses when their warning lights are on.
- It is forbidden to consume alcohol in a vehicle. The legal blood alcohol limit is 0.08, and violations result in imprisonment.
- You are allowed to turn right at a red light unless otherwise indicated.
- There is a minimum speed limit of 45 mph (72 km/h) on interstates and highways.
- The maximum speed limit varies from 105-120 km/h (65-75 mph).
- Motorcycles are not allowed to drive in the innermost lane in cities; this lane is reserved for public transportation.
Time Zones: On the continental US, there are four time zones:
- Eastern Time
- Central Time
- Mountain Time
- Pacific Time Each time zone differs by one hour.
Measurements: Distance/Length:
- 1 Mile = 1.6 km
- 1 Foot = 30 cm
- 1 Inch = 2.54 cm
- 1 US pint = 0.5 liters
- 1 US gallon = 3.8 liters
- 1 km = 0.6 miles
Temperatures: In the USA, Fahrenheit is used instead of Celsius:
- 0 Celsius = 32 Fahrenheit
- 20 Celsius = 68 Fahrenheit
- 30 Celsius = 86 Fahrenheit
- 35 Celsius = 95 Fahrenheit.
Motorcycle Riding
We prioritize 100% safety during the ride, and we ride in a diagonal pattern known as the “zipper formation.” The guide’s vehicle leads the group, and the most experienced riders form the rear position, regardless of the situation.
We ride in a staggered formation, maintaining a moderate distance between motorcycles, neither too far nor too close, and form a long snake-like line. On Route 66, we usually have narrow roads to ourselves. In areas where Route 66 is no longer accessible or doesn’t exist, we will ride on Interstate 40 and generally stay in the second innermost lane. This is the most practical approach, as it allows us to avoid dealing with vehicles exiting on the right side.
The speed will be comfortable and not too fast. We usually get to ride relatively undisturbed by other traffic. We provide vests to be worn after dark. The guide will provide all necessary instructions, explanations, and safety tips when we pick up the motorcycles. It is important that everyone pays attention to this information.
Be patient with each other, especially during the first few days when participants are getting accustomed to the bikes and American roads. We hope and believe that everything will go smoothly, and remember, we are here to have fun!
All guides have American mobile phones, so write down their numbers and keep them in your pocket along with a fully charged mobile phone.
Emergency Stop
If something happens on the road that requires you to stop (if you feel unwell in any way), raise your left arm and keep it up until the person in front of you does the same. This signal will make the guide leading the group stop the lead bike. (Do this before you become seriously ill.)
If you suddenly become ill and need to stop immediately: Pull off to the side of the road and as far away from traffic as possible. Only the last motorcycle will stop!! It is too dangerous to have more than 20 motorcycles stopping immediately along the road. The rest of the group will not leave you behind but will stop as soon as possible.
Take care of each other
Everyone is responsible for keeping an eye on the person behind them by using their mirrors. If half of the group manages to go through a green light, but the others have to stop at a red light, it is the responsibility of the person who made it through the green light to wait for the rest of the group. If they slow down, the vehicles in front will also slow down. This way, we can keep the group together as much as possible.
Be cautious and check the mirrors frequently to ensure no one loses complete contact with the group. This will help us avoid uncomfortable or dangerous situations where people may feel stressed or scared. Each day, there will be an experienced and reliable person riding at the rear of the group.
Drinking while riding
Bring water bottles that can be opened and closed with your teeth. This way, you can drink with your left hand while steering with your right hand. Place the bottles upside down between the handlebars and the windshield. The guides sell water and other drinks from the lead vehicle every day. They may also make stops at places other than gas stations.
Speed and Safety
We constantly strive to maintain a comfortable pace that suits all participants. This means that some may find it comfortable, while others may feel it’s a bit slow, and some may think it’s a bit fast. However, on highways, we must maintain a speed that matches the flow of traffic. Be very clear in signaling your intentions to others.
Americans generally behave politely on the road and usually show moderation when riding as a group. Try to read the traffic, use common sense, and avoid taking risks.
Americans generally behave politely on the road and usually show moderation when riding as a group. Try to read the traffic, use common sense, and avoid taking risks.
Breaks and Roadside Stops
We usually stop every hour. Some stops are short, about 10-15 minutes, for stretching your legs, using the restroom, buying drinks, or other needs. Other stops can last from 30 to 90 minutes and are planned by the guides for visiting attractions or other purposes.
Lunch Break
After two to three hours on the road, we stop for lunch, typically for 45 minutes to an hour. This will be planned by the guide. Those who feel hungry or want to snack before or after the lunch break can purchase a hot dog, sandwich, or other food options.
When stopping at gas stations to refuel, avoid ordering large meals as it will delay the trip and may cause us to miss scheduled activities. We recommend that everyone bring some salty snacks to eat while on the motorcycles (peanuts, dried meat, etc.). You can purchase more of these snacks at gas station stops along the way.
Refueling
We refuel every two hours. Everyone should refuel at each designated stop, even if their tank is almost full. Some motorcycles have smaller fuel tanks than others, so we need to stop regularly for their sake. Fuel gauges can be inaccurate, so we always fill up to the maximum each time.
When the lead vehicle pulls into a gas station and signals to refuel, we form two lines at the pumps. The guide will start the pumps and instruct everyone to help refuel all the motorcycles. All engines must be turned off while refueling for environmental reasons, and each rider pushes their bike to the pump when their turn comes.
Those at the end of the queue have time to use the restroom while the first motorcycles refuel, and vice versa. The person responsible for refueling keeps track of the amount and price of each fill-up, which is provided to the guide before hanging up the pump. For those who wish to ride alone, they need to remember to keep receipts for fuel purchases and arrive the next day with a full tank.
Roads and Route 66
Only about 80% of Route 66 exists today. Some sections of the road are damaged or closed, while others are narrow with speed limits of 20 or 30 km/h.
We cover as much of the original Route 66 between Chicago and Los Angeles in both directions as possible. This way, you get to see the highlights along the way. We guarantee that you won’t miss out on the worthwhile attractions. If you want to see something specific, talk to the guide, and we’ll try to accommodate it. It’s entirely up to you whether you want to follow the lead vehicle or ride on your own. Just remember to inform the guide to avoid unnecessary confusion or worry along the way. On some days of the trip, we will need to ride on Interstate 40 or other modern roads to reach the day’s final destination.
Emergency phone numbers
Dial 911 for the police, ambulance, and fire department.
Always have the number of your insurance company with you.
If you lose your credit card
VISA: Call (800) 336 8472 American Express: Call (800) 528 4800 Mastercard: Call (800) 826 2181 Lost traveler’s checks: Thomas Cook Assistance – Call (800) 223 7373
If you lose your passport
A lost passport must be reported to the police immediately in the USA. Then you must report it to your country’s embassy or consulate so they can issue an emergency passport. There is usually a fee for issuing an emergency passport. An emergency passport can only be issued to individuals who can confirm their citizenship in their country.