New York & Chicago
Discover the energy and history of America’s most iconic cities on this 11-day adventure through New York, Chicago, and the heartland in between. From powerful landmarks like the Statue of Liberty and the 9/11 Memorial to unique stops such as Bicycle Heaven, Hershey’s Chocolate Lab, and the Rock and Roll Hall of Fame, each day brings something memorable. Guests will enjoy a balance of big-city excitement, scenic countryside travel, and special museum visits along the way. It’s a warm, engaging tour perfect for travelers who enjoy culture, history, and unforgettable stories.
Tour Dates:
• Sept 1 – Sept 11, 2026
Day 1 – Terre Haute, IN
We’re traveling from Missouri to Terre Haute, IN today. It’s a laid-back travel day, perfect for napping, snacking, or swapping stories with your seatmate as we roll through the heartland.
Day 2 – Indiana War Memorial
Today we head to Indianapolis where we’ll visit the Indiana War Memorial, a museum filled with American military history from the Revolutionary War to now. Then it’s off to Zanesville, OH, where we’ll have dinner in the German Village before settling in at our hotel.
Day 3 – Bicycle Heaven
Still have that old bike from days gone by? Today we stop at Bicycle Heaven in Pittsburgh, PA. There we’ll see over 4,000 vintage to new bicycles, plus a collection of memorabilia and theme bikes. We’ll also visit Phipps Conservatory and Botanical Gardens, one of the nation’s oldest Victorian greenhouses. This afternoon, we’ll drive to the “Sweetest Place on Earth”—Hershey, PA.
Day 4 – Hershey Chocolate Lab
This morning we’ll tour the Hershey Museum, The Chocolate Lab, and make our own candy bar. Afterwards, we’ll head to Philadelphia, PA for a tour of this historic city.
Day 5 & 6 – New York City, NY
New York City currently houses 8.4 million people distributed over a land area of 305 square miles. We’ll spend the next two days on a guided tour seeing and doing as much as we can in this amazing city! We’ll see the Statue of Liberty, Ellis Island, and go to the top of One World Trade Center. We’ll go into Central Park for a short while but spend quite a bit of time at the 9/11 Memorial. We’ll also drive through Times Square, Rockefeller Center, where they film the Today Show, see Madison Square Garden, Wall Street, and Broadway. So much to do and see… these two days are packed with excitement!
Day 7 – Scenic Pennsylvania
We say goodbye to NY and cruise through beautiful Pennsylvania to our hotel in Clearfield. Along the way, we will stop at a winery for a little sampling of the wares.
Day 8 – Rock and Roll Hall of Fame
We’re headed to Toledo, OH. Along the way we’ll stop in Cleveland to visit the Rock and Roll Hall of Fame Museum, which is dedicated to the celebration and preservation of rock and roll music from the 50s through today.
Day 9 – Chicago, IL
Chicago is big and bold. You’ll have the option to tour the city via double-decker bus or the downtown area on a riverboat. We’ll visit the famous Navy Pier for their shops and dinner. We’ll spend tonight just outside Chicago.
Day 10 – Route 66 Hall of Fame Museum
This morning we’ll visit the Route 66 Hall of Fame Museum in Pontiac, IL. You’ll see several icons of Route 66 and a lot of military history. We’ll take a group picture in front of the world’s largest Route 66 mural. This afternoon, we tour the Caterpillar Museum in Peoria, IL. This is a special place for anybody who’s ever operated heavy machinery.
Day 11 – Home
As we make our way back to Missouri, we carry memories from the bright lights of New York City, the bold skyline of Chicago, and the legendary sounds of Rock & Roll. It’s been a whirlwind journey of iconic cities, rich history, and unforgettable music—but there’s no place like home.