The Mighty Mississippi is one of the world’s most famous rivers. This tour takes you on a journey from Chicago to New Orleans going through some of rural heartland and delightful small towns and cities to which the river gave birth. Experience traditional blues music, with a mix of gospel and soul. Great musicians emerge and thrive in the cities from where their music first caught the world’s imagination.

Explore this magnificent city built around Lake Michigan, including the curving Lakeside Drive and the stunning views of the skyline, dominated by The Willis Tower. The view from the Skydeck offers a breathtaking panorama over the city and the lake beyond. Stroll the grounds of Millennium Park and take a look at the reflective Cloud Gate Sculpture, aka “The Bean “ or stroll along the Chicago River then head into downtown, with a thriving centre of boutiques, cafés, restaurants and specialist shops, lively by day and night. This evening, try a famous Chicago-style pizza and afterwards check out some of the many famous Chicago Blues and Jazz clubs.

Stay two nights in Chicago.

Collect your car and head out of the city, across the state to the Mississippi River. Named one of the Top 10 Most Romantic Small Towns in North America, Galena is nestled in northwest Illinois is an ideal location to discover the region’s beautiful scenery, with rolling hills, lush valleys, and the Mississippi River. Enjoy hiking, fishing, kayaking and golfing, or take a tour of one of the area’s many vineyards and wineries. The downtown area boasts historic buildings, charming boutiques, art galleries and restaurants.

Stay one night in Galena.

Take a stroll down Maine Street and admire the array of restaurants, bars and boutiques housed in historic buildings. The whole downtown area of Quincy is listed on the National Historic Register. View the historic mansions in the East End Historic District, admire the ornate gilded woodwork in the Quincy Museum and stop for lunch at Thyme Square, a farm-to-plate restaurant right in the centre of downtown. 

Stay one night in Quincy.

Take a short drive to Hannibal and tour the town on an old-fashioned trolley ride. Step back in time and relive the adventures of Mark Twain’s days here. With many locally-owned shops, restaurants, art galleries and boutiques, Main Street is the perfect place to stroll, shop and take in the beautiful Mississippi River views.   

Visit the Mark Twain Cave Complex – where a guide will escort you on a one-hour tour featuring points of interest mentioned in Mark Twain’s writings. After your cave adventure, head over to Cave Hollow West Winery and sample wines you can only purchase in Hannibal, many of which are named for Mark Twain’s famous works. Tour the Molly Brown Birthplace and Museum to discover how Molly Brown’s rags-to-riches story which began in Hannibal and almost ended on the ill-fated Titanic voyage. Margaret Tobin (later known as “The Unsinkable Molly Brown”) was born in Hannibal and lived there for 17 years before moving on to Colorado to find fame and fortune. 

Enjoy dinner on the Mark Twain Mississippi Riverboat seeing this famous river town from the River or watch theatre productions about Mark Twain at the Planters Barn Theatre in Hannibal.

Stay one night in Hannibal.

Before you arrive in St Louis, the Great River Road crosses back into Illinois where you can make a stop at Grafton and you can soar through the air on an exhilarating ride at the Aerie’s Resort, taking in the stunning views of the Mississippi River from a height! 

St Louis boasts the nation’s tallest monument at 630-feet, the St Louis Gateway Arch. The Gateway Arch has beckoned visitors for more than 40 years with its iconic, awe-inspiring shape, and commemorates Thomas Jefferson and St Louis’ role in the Westward Expansion of the United States. Why not sample one of America’s world-renowned beers at the Anheuser-Busch Brewery, or take a sightseeing trip on the Mississippi River to get a different perspective on the city’s skyline. There are many unique neighbourhoods waiting to be discovered, and don’t miss a stop at Route 66 icon, Ted Drewes Frozen Custard for a treat you won’t forget!

Stay two nights in St Louis.

Head south to Memphis, the heartland of gospel and birthplace of Rock ‘n’ Roll. No visit to Memphis would be complete without a visit to Graceland, home of Elvis Presley. Explore the mansion and grounds of his 14-acre estate, whether you are a fan or not, you can’t help but be enthralled at this incredible home. Tour the famous Sun Studio where Elvis Presley, Johnny Cash and B.B. King first recorded, and visit the Stax Museum of Rock and Soul in downtown to really get an in-depth experience of the music icons that spent time here. Take a paddle-wheeler trip on the mighty Mississippi or visit Mud Island River Park and the Swiss-made monorail which offers great views of downtown Memphis, the Mississippi River and Mud Island itself.

Spend your evenings on Beale Street, where W.C. Handy first penned the Blues music of the Mississippi Delta. Stretching for several blocks, you can enjoy bars, nightclubs and restaurants offering a variety of food and live music, including traditional Blues, Rhythm and Blues, Jazz and Rock ‘n’ Roll. Be sure to hear live Blues at BB King’s or Rum Boogie Café.

Stay three nights in Memphis.

Continue to follow the Ol’ Man River to Natchez. Along the way make a stop at Clarksdale and the Delta Blues Museum, to give you the chance to explore the history and heritage of the unique American musical art form of the Blues. Founded in 1716 by the French and named after the Indians who dwelt there, this unique town is recognized as the oldest settlement on the Mississippi River. Visit the Frogmore Plantation, a cotton plantation of the early 1800s and still producing cotton and gin today. Learn of the early Natchez planters and their slaves, following their evolution from the wilderness to the thriving 1850s cotton plantation, beyond the ‘War Between the States’ to a struggling new way of life. Examples of authentically furnished slave quarters can be seen. Natchez boasts some beautiful antebellum homes and a historic downtown area, with good restaurants and local shops.

Stay two nights in Natchez.

Today, visit the Oak Alley Plantation protected as a National Historic Landmark. It is named after its alley or canopied path created by a double row of live oaks planted in the early 18th century, which runs between the house and the Mississippi River. The perfect way to sample the mix of cultures in New Orleans is to stroll along Bourbon Street in the French Quarter, listening for the vibrant sounds of jazz, blues and Zydeco. There are plenty of bars and restaurants for al fresco dining, perhaps sampling some of the city’s famous Creole and Cajun cuisine. The glass enclosed Spanish Plaza emporium down by the riverfront is a dramatic contrast to the French Quarter and is well worth a visit. Take a ride on the famous St Charles Streetcar; visit the Jackson Square Katrina museums or shop at the Riverwalk. The state of Louisiana offers tax free shopping for international visitors at over 1,000 stores, so shopping in New Orleans offers a unique opportunity. Why not end your holiday with an evening of traditional Jazz on a dinner cruise along the mighty Mississippi.

Stay two nights in New Orleans.