My American Holiday

13 days/12 nights
1670 miles / 2672 km



Depart the UK for your flight to Chicago, arriving the same day. On arrival, pick up your hire car and make your way into the Windy City. Why not spend your first evening listening to some live music in one of Chicago’s famous jazz and blues clubs? Stay 1 night at the Hotel Monaco (or similar).

miles / km


Make your way out of Chicago today and head for Milwaukee, Wisconsin. This former brewing powerhouse now boasts plenty of cultural and historic sites along with abundant beer halls and taverns. The Milwaukee Art Museum is worth visiting, not only for its impressive collection of 30,000 artworks but also for its distinctive Modernist architecture. For petrol heads, the Harley-Davidson Museum is also a must-see. From Milwaukee, continue into Door County, a peninsula known as ‘Cape Cod of the Midwest’ thanks to 30 miles of coastline and ten lighthouses. Stay 2 nights at the Eagle Harbor Inn, Ephraim (or similar).

259 miles / 414 km

Door County

Spend the day exploring this picture postcard corner of the Great Lakes today. Hunt for treasures in boutique shops, galleries and lighthouses. Pick a punnet of delicious Door County cherries in the summer or a basket of ripe apples in the autumn. Or you might like to explore the area from the water by chartering a boat for fishing, taking a sailing or kayak tour or exploring underwater on a scuba diving excursion.

miles / km

Spring Green

Travel west today towards Spring Green. Along the way, you can make a stop in Baraboo, home to the Circus World Museum. This fantastic museum was once the home of the Ringling Brothers circus and is now America’s largest library of circus information. Among the exhibits on show is a collection of circus wagons which are occasionally paraded through the streets of Baraboo in the Great Circus Parade. Continue onto Spring Green for the night. Stay 1 night at the House on the Rock Inn (or similar).

miles / 411 km


Spring Green was the home of famous American architect Frank Lloyd Wright and you can visit his beautifully designed home, House on the Rock. This house also contains some of the world’s most eclectic and rare collections ranging from an intricately furnished dolls house to the world’s largest indoor carousel. After lunch in Spring Green, continue your journey to Winona. This lush valley town on the banks of the Mississippi River looks as if it could be a Rhineland town in Germany. Stay 1 night at the Alexander Mansion (or similar).

129 miles / 206 km

Minneapolis/St Paul

Your route takes you along the banks of the mighty Mississippi today as you drive to the Twin Cities of Minneapolis and St Paul. Make your way to your hotel and then head out to discover this vibrant destination. A great place to start is the Riverfront District, the historic hub of Minneapolis, boasting historic buildings, cultural venues, scenic parkland, eclectic shopping and dining, all with the St. Antony Falls on the Mississippi as a dramatic backdrop. If you want some retail therapy, nearby Bloomington offers the largest shopping mall in the USA, the Mall of America. You’ll overnight in St Paul’s most unique inn, a restored tug boat on the Mississippi! Stay 1 night at the Covington Inn (or similar).

148 miles / 237 km


Bayfield is a pretty town that serves as the gateway to the stunning Apostle Islands National Lakeshore, encompassing 21 wilderness islands and over 12 miles of beautiful unspoilt shoreline. You’ll have two days to explore here. Your accommodation for the night is in Bayfield’s first Bed and Breakfast, an elegant hotel with period furnishings and gorgeous stained glass windows. Stay 2 nights in the Rittenhouse Inn (or similar)

208 miles / 333 km


Perhaps enjoy another morning in Bayfield before setting off across the Upper Peninsula to Marquette. The Upper Peninsula is bounded by Lake Superior to the north, St Mary’s River to the east and Lakes Michigan and Huron to the southeast. This abundance of scenic coastline makes this area a paradise for water sports such as boating, kayaking and fishing as well as hiking in the summer and snowmobiling in winter. Stay 1 night at the Landmark Inn, Marquette (or similar).

205 miles / 328 km

Mackinac Island

Drive to Mackinaw City this morning and board a hi-speed ferry for the 20 minute journey to Mackinac Island. Here you’ll feel as if you’ve gone back in time with a ban on cars and lovely Victorian architecture predominating. You might also like to take a horse and coach ride or try some of the fudge that the island is famous for. Spend 2 nights at the Grand Hotel Mackinac Island (or similar).

171 miles / 274 km


Take the ferry back to the mainland this morning, collect your car and make your way to Saugatuck. This is one of Michigan’s favourite beach destinations, with an abundance of history, culture and annual festivals on the shores of Lake Michigan. Stroll along the beautiful boardwalk, relax on one of many beaches and discover historic local lighthouses. Stay 1 night at the Beachway Resort & Hotel (or similar).

293 miles / 469 km


There should be time to make a couple of leisurely stops in the beach communities of Holland and Grand Haven today, en route back to Chicago. Once you arrive back into the Windy City, make your way to the airport to drop off your hire car and board your flight back to the UK.

miles / km