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Lake Geneva, Chicago, and
Frank Lloyd Wright

Sept. 13-15 


DAY 1 – Friday – Sept. 13 – Lake Geneva, Wisconsin 

Welcome aboard! Sit back and relax as we drive through Southern Wisconsin to Lake Geneva. When we arrive, we will board the U.S. Mailboat for a tour of Lake Geneva. There are only a handful of places left in the country where mail is still delivered by boat, and none with a more exciting and scenic tour than this!


With over 100 years of mail service, mail is still delivered to about 75 homes around the lake on a daily basis. You’ll see the agile and athletic mail-jumper deliver mail by jumping off the moving boat as it navigates between the piers on the shoreline. Get a very in-depth narration of the Lake Geneva area and its ties to Chicago. You will also see the beautiful mansions on the lake along with the original Wrigley Estate comprised of six different homes. You will then have time for lunch and exploring on your own in Lake Geneva before we check into our hotel in Elkhorn, Wisconsin. 


Tonight enjoy the Dancing Horses, a longtime dream of owner and creator Dana Montana. She wanted to share the beauty and talent of her beloved Arabian Horses with others, and the dream of The Dancing Horses became a reality 20 years ago. Along with her daughters Danette and Danelle, they produce The Dancing Horses Show. 

Dinner Included


DAY 2 - Saturday – Sept. 14 – Chicago

This morning, we travel to Chicago where we go  back to the 1920's & 1930’s, on our Barrel Run Gangster Tour. This is a tour all you guys and dolls will enjoy! Our gangster guides present an accurate account of the crimes and activities that were going on in Chicago during the 1920s and ’30s (Prohibition Era).  


You will hear the exploits of Capone, Moran, Dillinger and the rest of the boys on this unforgettable Chicago crime tour! Some sites included are: the St. Valentine’s Day Massacre and ​Holy Name Cathedral. A stop will be made at a local brewery for tasting. The tour is educational and very entertaining. 

This afternoon we board the Wendella Boat for an architectural tour along the Chicago River. The journey begins with an up-close perspective of Chicago’s internationally-known architecture as seen from the Chicago River. Then, venture through the Chicago Lock to gain a new perspective of Chicago’s architecture from Lake Michigan.  This evening you are the guest of Her Majesty Doña Maria Isabella at the Medieval Castle. Upon arrival, you will be crowned with the colors of your kingdom. Warm up your voices and get ready to cheer your brave knight to victory! The queen oversees the tournament and only one knight will win the tournament and be named Defender of the Throne!   

Breakfast and Dinner Included



DAY 3 -  Sunday – Sept. 15 – Frank Lloyd Wright

Home and Studio

Following breakfast at the hotel we travel to Frank Lloyd Wright’s first home and studio (1889-1909) the birthplace of an architectural revolution. Wright used his home to explore design concepts that contained the seeds of his architectural philosophy. In his adjacent studio, Wright and his associates developed a new American architecture – the Prairie style. The historic district surrounding the Home and Studio has the greatest number of Wright-designed residences worldwide. 


The home and studio sits on the ancestral lands of the Potawatomi, Miami, Kickapoo, and Peoria Nations. Today, Native peoples from over 100 tribes live in the Chicago area, one of the largest urban American Indian communities in the United States. Native peoples continue to contribute to the life of this region by celebrating their heritage, practicing traditions, and caring for the land and waterways. Following a stop for lunch we begin making our way home with many great memories of our 3-day adventure to Lake Geneva and Chicago.   

Breakfast Included


Guaranteed Pick Up Points: Cuba City, Platteville, WI & The Q Casino Dubuque, IA.



• Deluxe Motorcoach

• Full Time D&D Custom Travel Tour Director

• 2 nights lodging

• 2 Breakfasts

• 2 Dinner

• Lake Geneva Mailboat Tour

• The Dancing Horses

• Barrel Run Gangster Tour

• Brewery Tasting

• Wendella Architectural Tour

• Medieval Times

Dinner/ Show

• Frank Lloyd Wright Home and Studio


Taxes and Gratuities on All Included Meals and Attractions


Price per person

$855.00 per person – 4 to a room

$885.00 per person – 3 to a room

$945.00 per person – 2 to a room $1135.00 per person - single

$100 Deposit per person due with reservation


 Final Sign Up and Final Payment due Aug. 12, 2024


Even the most carefully planned trip can be complicated by unforeseen events. 

To protect your investment. D & D Custom Travel LLC will provide Travel Insurance information upon request.

Make a reservation


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