Love Along the River: St. Charles & St. Louis

Day 1

Trade winter’s chill for a weekend of warm hospitality, fascinating history, and St. Louis charm! From the cobblestone streets of St. Charles to the grandeur of the Fabulous Fox Theatre, this getaway blends Midwest heritage, iconic attractions, and plenty of time to explore at your own pace.


Day 1 – Friday, February 6, 2026
History and Charm in St. Charles
Settle in aboard your deluxe Windstar motorcoach and relax as we roll south toward Missouri’s gateway city. The journey includes comfortable stops and plenty of sightseeing from your window seat before our first destination—the Lewis & Clark Boat House and Museum in St. Charles. Step back into the days of the great expedition as you explore full-scale replicas of keelboats, fascinating Native American artifacts, and exhibits highlighting the natural wonders and challenges faced by the Corps of Discovery. Don’t miss the breathtaking Missouri River Walk—the largest indoor mural in the state!
Just a few minutes away, the Historic Main Street District of St. Charles invites you to wander through more than a hundred locally owned boutiques, galleries, and specialty shops. From gourmet spices and handcrafted jewelry to antiques and art, this riverside district offers a perfect mix of nostalgia and novelty.
As evening sets in, we’ll check into the Drury Plaza Hotel Chesterfield, where comfort meets convenience. Enjoy the Drury’s famous Kickback Reception—a complimentary light dinner and drinks—or head out to one of the nearby restaurants for dinner on your own. Rest up, because tomorrow we explore the heart of St. Louis!

Day 2

Day 2 – Saturday, February 7, 2026
Culture, Craft & Creativity
After a hearty hotel breakfast, we begin our day with a behind-the-scenes guided tour of the Fabulous Fox Theatre—a 1929 masterpiece known as one of the most magnificent theatres in the world. Gilded ceilings, Moorish design, and a storybook atmosphere await as you uncover the theatre’s glamorous past and peek into areas few visitors ever see.
Next, we’ll head to City Foundry STL, an energetic food hall and marketplace housed in a reimagined industrial complex. Grab lunch on your own from one of the many local eateries—everything from tacos to Thai street food—and take in the creative vibe that makes this one of St. Louis’s trendiest gathering places.
Our afternoon features a tour of the legendary Anheuser-Busch Brewery, where you’ll discover how tradition, craftsmanship, and innovation blend to create one of America’s most iconic beverages. Then, we visit the World Chess Hall of Fame & Galleries, a hidden gem in the Central West End. Enjoy a guided tour through the world’s largest chess-piece collection, learn about the game’s rich history, and even take part in a lighthearted chess lesson.
Tonight, gather with fellow travelers for a group dinner at a local favorite restaurant, where good food and great company make the perfect finale to a fun-filled day.

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Day 3 – Sunday, February 8, 2026
Love and Laughter in St. Charles
Following breakfast, we bid farewell to Chesterfield and make our way back to St. Charles for a whimsical celebration—Once Upon a Valentine on Main. This lively micro-festival offers something for everyone: romantic strolls, quirky entertainment, creative vendors, and even a few tongue-in-cheek “anti-Valentine” attractions. Whether you’re a hopeless romantic or just here for the laughter, this one-of-a-kind event will leave you smiling.
As the afternoon winds down, we’ll board our Windstar motorcoach for the journey home—hearts full, shopping bags filled, and memories made with friends old and new.