From Great River to Great lake
DAY 1: Chicago-Rockford, Illinois (89mi/ 143 km)
Arrive Chicago O’Hare and transfer to Rockford, Illinois. Stretch your legs after the long flight and explore the rich architectural history of Haight Village by foot. Rockford’s only residential National Register Historic District , it encompasses a fourteen-block area that blends a unique mixture of Victorian elegance and urban living.

DAY 2: Rockford-Galena, Illinois (78 mi/ 126 km)
Before departing Rockford, visit one of its renowned botanical gardens. See the natural beauty Anderson Japanese Gardens, ranked the top Japanese Garden in North America. Continue to explore different countries among the 150 acres of trees and plants from around the world at Rockford’s secret garden, Klehm Arboretum & Botanic Garden. Then travel west to the former mining town of Galena. Stroll its quaint Main Street this afternoon, consistently voted best Main St. in the Midwest. Here one will find a plethora of specialty shops, restaurants, art galleries, boutiques, and historic attractions which charmingly occupy mid–19th century storefronts.

DAY 3: Galena-Winona, Minnesota (161 mi/ 259 km)
This morning visit the Ulysses S. Grant Home, where the future President of the United States lived . Then follow the Great River Road north into Minnesota to the River town of Winona. Often likened to the Rhine in Germany, Winona is a lush valley town on the banks of the Mississippi River and is surrounded by natural beauty. Spend the evening at a â€œDestination” Bed & Breakfast with elegant turn-of-the-century craftsmanship, magnificently restored to its 1886 Victorian splendor.

DAY 4: Winona-Minneapolis/St. Paul (148mi/238km)
Drive along the mighty Mississippi today to the Twin Cities. Here you’ll find a variety of districts with things to do. Visit the Riverfront District, the historic \"birthplace of Minneapolis with an eclectic collection of historic buildings, scenic parks, cultural venues, dining, and shopping, with the inspiring St. Anthony Falls on the Mississippi River as a dramatic backdrop. Spend the next two nights at the most unique Inn in the city of St. Paul and beyond, a restored tugboat berthed in the Mississippi!

DAY 5: Minneapolis/St Paul
Today one can easily spend a full day at the Mall of America in neighboring Bloomington, the largest mall in the country. Or if shopping’s not of interest, take a walking tour of the city’s Victorian neighborhoods, the historic Warehouse district and Nicolette Island. Spend the evening along the Minneapolis’ Riverfront where bars and restaurants abound.

DAY 6: Minneapolis/St. Paul-Spring Green (240 mi/ 386 km)
Travel east to Spring Green, visiting Baraboo en route. Baraboo is home to the Circus World Museum, the former headquarters and winter home of the Ringling Brothers circus and now the largest library of circus information in the United States. This living museum has a collection of circus wagons, and occasionally hosts the Great Circus Parade of these artifacts through the streets of Baraboo. The Al. Ringling Theatre is an active landmark in the city. This grand scale movie palace is larger and more elaborate than one would normally find in a town the size of Baraboo, owing to the financial assistance of the Ringling family. The Al Ringling home still exists and is maintained in good condition. Continue into Spring Green for the night.

DAY 7: Spring Green-Winona (129mi/207km)
Today, visit two premier attractions in Spring Green, the Taliesin Estate and House on the Rock. Frank Lloyd Wright, America’s premier architect and Wisconsin’s native son considered Spring Green his home, and he built and created an environment both beautiful and inspirational. House on the Rock has room after room of some of the world’s most unique and eclectic collections from the smallest detail of an intricately furnished doll house collection to the world’s largest indoor carousel. Each exhibit is filled with the exotic, the majestic, and the unexpected.

DAY 8: Spring Green-Milwaukee (123 mi/ 198 km)
Take a leisurely drive to Milwaukee. Once known almost exclusively as a brewing powerhouse, the city now boasts the beautiful Milwaukee Riverwalk and Milwaukee Art Museum, with its architecturally impressive addition designed by Santiago Calatrava. The modernist building is shaped like a floating cross, with wings opening and closing from a central base. Even people who’ve never been on a motorcycle will enjoy the Harley-Davidson Museum. Exhibits tell the stories of the extraordinary people, products, history and culture of Harley-Davidson and of-course the fantastic motorcycle collection will captivate all.

DAY 9: Milwaukee-Chicago, Illinois(92 mi/ 148 km)
Depart for Chicago this morning. Time allowing, do some last minute shopping along Chicago’s famous Magnificent Mile before transferring to the airport.


Lexington Hotel


The Irish Cottage


Alexander Mansion


The Commons

Spring Green

House n the Rock


Courtyard Downtown

Package Includes:
  • Accommodation
  • Taxes
  • Fly - Drive directions and information packet at hotel upon arrival