Jeep Wrangler Driving Tour in the Mississippi Delta

Guiding visitors through the Mississippi Delta with hundreds of five-star reviews and unforgettable stories from the backroads of Coahoma County.
Meet Chilly Billy
Your Guide to the Mississippi Delta Backroads
Billy Howell, known locally as “Chilly Billy,” is a Delta-born storyteller, philosopher, and lifelong student of the history and people of the Mississippi Delta and Coahoma County. A passionate reader and world traveler, Billy brings the region to life through humor, stories, and unforgettable encounters along the backroads of the Delta.
These are not scripted tours. Billy has spent decades exploring the Delta and knows the characters, stories, and hidden places that rarely appear in guidebooks.
Along the levee you might even meet Whistle, the guard donkey, who recognizes Billy’s Jeep and comes running, honking with excitement, for the apple Billy always carries in case he passes the levee pasture.
Visitors often say the tour helps them understand the Delta in a way that books and museums alone cannot.
Tour Options and Pricing
Choose the Delta experience that fits your schedule. Each tour is private and led personally by Chilly Billy.
REGIONAL-IDENTITY TOUR
REGIONAL-IDENTITY TOUR
1 guest – $280 total
2 guests – $300 total
3 guests – $320 total
4 guests – $340 total
The private, in-depth Regional-Identity Tour is approximately 2 1/2 hours in a comfortable, air-conditioned, Jeep Wrangler and includes a driving history of Coahoma County, beginning with the macro to the micro. As we head toward Muddy Water’s homesite, we define the Delta geographically and culturally, while discussing in detail all-things agricultural. Next, a ride on the levee and a visit to Friars Point and the Mississippi River, where river history and its specifics are narrated on the banks, and Friars Point’s fantastic music, river and civil war history are delineated.
The final and shorter leg of the Regional-Identity Tour focuses on Clarksdale, its founding and pre-history, Tennessee Williams and blues history, the musical and Civil Rights poignancy of New World District, with a thorough acclimation to current music venues and restaurants.
The Regional-Identity Tour allows for an in-depth conversation about agriculture, what defines the Mississippi Delta, present and past socio-economics, and how all these threads weave together to form a unique, diversified, cultural fabric! It’s a wealth of information! BOOK NOW!
EXTENDED REGIONAL-IDENTITY TOUR
EXTENDED REGIONAL-IDENTITY TOUR
1 guest – $320 total
2 guests – $340 total
3 guests – $360 total
4 guests – $380 total
Includes all the elements of the Regional-Identity Tour plus either a visit to the Hopson Plantation and/or a pickup at the Shack Up Inn.
The Extended Regional-Identity tour is approximately 3 hours in length.
Contact Chilly Billy directly for a customized, farther-reaching, contractable tour assessed on an hourly basis. We can visit other Delta towns, grave sites and even a visit to Helena, Arkansas on the other side of the Mississippi River. Your time and money buy my drive time.
What Guests Say About Touring with Chilly Billy
“Five stars hardly do justice to the depth of Chilly Billy’s knowledge about the Delta and the richness of his local stories.” — TripAdvisor Review
CONTACT CHILLY BILLY AND BOOK YOUR TOUR
PAYMENTS
Billy accepts cash or credit card payments.
Tips are appreciated.
DAILY TOURS
Chilly Billy only gives one tour per day in order to ensure that he is fully present and fresh for all his touristas.
PHOTOGRAPHY
Please feel free to take pictures, but videotaping and audiotaping of Chilly Billy’s presentation is not allowed. Happy to snap pics of y’all at any time!
CELL PHONES
Please mute all cell phones while on tour. The regional-identity tour requires focus in order to understand our laidback area. Host will not talk over cell phones or cross dialogue.
DISCOUNTS AND COMBINING TOURS
Discounts are NOT available. Please do not ask for one.
All tours are private. We do not combine separate groups and/or individuals. We offer relational tours only.
HOURS OF OPERATION
Tours are given seven days a week
OUR LOCATION FOR PICKUPS
Our address is at iconic landmark and shared with Abe’s Bar-B-Q at 616 N. State Street, Clarksdale, MS 38614, conveniently at The Crossroads, but we can also pick you up at the location of your choice or wherever you are staying in Clarksdale. These details will be finalized with Chilly Billy after booking your tour.
CONTACT FOR QUESTIONS
chillybilly@deltabohemian.com or 662-701-5020
