A 10-day motorcycle trip, crossing 8 states from south to north, retracing the cultural and historical path of the Great Migration in the United States (the movement of 6.5 million African-American citizens from the rural South to the big city in the North). The journey begins in New Orleans, the birthplace of jazz and blues, and winds through the Great Smoky Mountains, along the Tennessee Whiskey and Kentucky Bourbon Trails, culminating in Chicago, where the blues found its modern sound. Throughout the ride, we experience rich musical traditions, soulful cuisine (SOUL FOOD), spectacular landscapes, and timeless Americana.
A motorcycle adventure that celebrates the historic journey of culture, music, and spirit, while connecting riders to the landscapes and stories of the region.
6-17/10/2026 - last spots
12 days/11 nights
10
New Orleans
Chicago
2700
medium
100% asphalt
2000
Yes - recommended
easy+
A shared room with another rider is included as standard. See supplements for single room pricing.
All of our accommodations have been carefully selected to create an authentic experience without compromising on luxury.
Includes comprehensive insurance with a deductible of $1500-$2000 (depending on model)
We arrange the rental through our preferred supplier. Your contract will be directly with the supplier and you will be required to comply with their terms and conditions.
Breakfast + Dinner
Indulgent Gourmet Meals – A Culinary Experience
Customized
Leading and managed by an experienced member of the Caribou team.
Qualified as an international tour guide with extensive knowledge of the destination,
Trained in advanced riding
Qualified in first aid.
On every trip without exception, there is full support by an accompanying vehicle! It will carry all our luggage as well as essentials, tools, a medical kit (in addition to that carried by the main guide), cold drinks and snacks. There is always a free seat for any participant who might want to take a break.
From the airport to the hotel upon arrival and from the hotel to the airport on the day of departure.
All entrance fees to all attractions during the trip are included – and there are many attractions in each Trip
Shirt
Hat
Stickers
Neck warmer
Keychain
A portion of the proceeds from each trip participant goes directly to the Make-A-Wish Foundation, whose sole mission is to grant life-changing wishes to children ages 3-18 with serious illnesses.
We will hold a face-to-face meeting at least two weeks before departure.
During the meeting, we will present the trip in detail and answer any questions you may have. This is also an opportunity to get to know your travel partners and raise a toast together.
If you are unable to attend the meeting, we will arrange a personal video call.
You will need to book a flight and arrive at your destination before the trip begins. We will suggest a flight itinerary based on time/cost considerations. Although we provide you with a travel agent to take care of this, you are under no obligation to purchase through them.
If you purchase through another agent or directly, please ensure the following:
Do not book your flight until we have notified you that this departure is guaranteed.
Make sure to arrive before the trip begins (send us a copy of your flight for confirmation before purchasing)
You must take out travel insurance in case of cancellation (Passport Card).
At the beginning of the trip, we create a small cash pool that everyone contributes to (about 25 euros per day). This is used for coffee breaks, lunches and fuel.
This approach really helps to speed up all the stops along the way.
All beverages, whether alcoholic or not, are not included.
It is mandatory to take out travel insurance that covers emergency evacuation, medical bills, etc.
Souvenirs
Laundry
Damage to the motorcycle (motorcycle insurance is included in the rental but there is a deductible of $1500-$2000 depending on the model). Please note that this amount will be held on your credit card or paid as a deposit.
Towing, oil, spare parts, labor or other indirect costs resulting from damage to your motorcycle.
Emergency transportation
Anything not specifically stated as included.
Mandatory riding protective equipment:
Full-face helmet
Protective riding jacket
Knee protection: Knee pads or protective riding gaiters
Riding gloves
High-top shoes (above the ankle) or riding boots.
