So many people have said “I wish I could travel with you!” – so now, you can! I have a variety of one-day, three-day, five-day, and seven-day trips planned – from mystery trips to cruises, we will have FUN!
2026 Group Traveling Cheesehead Tours
If you are interested in any of these trips or want to learn more, just send us an email at DannelleGay@gmail.com
June 14-16: Rolling on the River: An Iowa Adventure
Get ready to cruise, laugh, and explore your way through the heart of the Midwest on this 3-day, 2-night getaway along the mighty Mississippi! From the fun-filled Quad Cities to the bluffs of beautiful Dubuque, this adventure blends river views, local flavors, and a splash of small-town charm. Step aboard a scenic Mississippi River cruise, visit fascinating museums, enjoy live entertainment, and savor hearty Midwest cooking at every stop.
It’s a perfect mix of relaxation and discovery—where every bend in the river brings a new surprise and a reason to smile.
$675 PP –
Get your tickets HERE
August 7-9: Wisconsin Native Nations Tour
This is more than a trip—it’s a journey of learning, connection, and cultural appreciation, and I’d love to share it with you.
The tour includes:
- Comfortable round-trip transportation from Sun Prairie (with a pickup stop en route)
- Overnight stays at tribally owned hotels
- Visits to Oneida, Stockbridge-Munsee, Sokaogon Mole Lake, Forest County Potawatomi, and Menominee Nations
- A traditional dinner, museum tours, art galleries, and more!
- The unforgettable experience of attending a real Pow Wow on the final day!
$1,200 Single, $2,100 Double (40 total spots available)
Get your tickets HERE
Sept 4-6 Wine Not Weekend in Michigan
Our Wine Not Weekend Tour is the perfect blend of bold flavors, local charm, and a little quirky indulgence—all with transportation and details handled for you.
🍇 Limited spots available—whether you’re a wine lover, curious foodie, or just in need of a fun escape with new friends, this is the kind of weekend that leaves you with great stories and a satisfied palate.
Your weekend includes:
- 2 Nights at the Drury Inn & Suites Grand Rapids
- Rest easy with comfortable accommodations, a hot breakfast, and evening kickbacks
- Brunch & Treats at Lambs Farm
- Cocktail & Cannoli Experience at North Shore Distillery
- Tram Tour of Frederik Meijer Gardens & Sculpture Park
- Paw Paw Wine Festival Admission + Grape Stomping
- Tour of Grasshopper Farms
- Lunch & Beer at Beer Church Brewing Company
- 5 Meals Included
- Round-trip Transportation + Baggage Handling for 1 Bag Per Person
$649 – 839 PP
Get Your Tickets HERE
December 4-6: Sleigh Bells & Shopping Bags: Twin Cities Holiday Magic
A festive weekend getaway filled with theater, treasures, and treats!
Join us for a sparkling seasonal escape to the Twin Cities! This all-inclusive holiday adventure features:
- A dazzling performance at the Chanhassen Dinner Theater
- Shopping at charming small boutiques and the Mall of America
- Two nights in a cozy hotel
- Delicious meals throughout the weekend
- Comfortable transportation and holiday surprises along the way
Get your tickets HERE
2027 Tours
May 1-3: The Klondike Chronicles: A Traveling Cheesehead Mystery
Pack your sense of adventure—and maybe your cowboy hat—because this 2-night, 3-day getaway is full of surprises!
From the moment Miss Lil sashays in with her bag of clues, you’ll be caught up in a wild mix of mystery, laughter, and a little Midwest mayhem. Along the way, you’ll discover sweet treats, quirky sights, and a few unexpected guests (watch out for Yukon and his reindeer friends!).
No spoilers here—just know that by the time the Klondike Kid makes an appearance, you’ll be grinning from ear to ear and have a happy belly.
For more information, go here: Klondike Trip
June 9-19: 11 Day AMAZING Alaskan Adventure
Experience the breathtaking beauty of America’s Last Frontier on this unforgettable 11-day land and sea journey through Alaska. From Anchorage to Vancouver, explore towering glaciers, gold rush towns, and pristine wilderness while traveling with Princess Cruises.
Highlights include:
- Overnight stays at Princess Wilderness Lodges near Mt. McKinley and Denali National Park
- Scenic rail journey aboard Princess’ exclusive Direct-to-the-Wilderness train service
- “Natural History Tour” of Denali National Park and optional Music of Denali dinner theater
- Visits to legendary destinations including Skagway, Juneau, and Ketchikan
- Awe-inspiring days cruising Hubbard Glacier and Glacier Bay National Park—both UNESCO World Heritage Sites
- Onboard enrichment programs led by National Park Rangers
- Walking food tour in Juneau – with one of the best tour guides in the country (not me, LOL)
- Delicious dining, stunning scenery, and memories to last a lifetime
Get your tickets HERE
July 12-15: The Shipshewana Sampler
Step back in time and experience the charm, craftsmanship, and culinary traditions of Amish Country on this unforgettable multi-day tour of Shipshewana, Indiana. From handwoven baskets to hearty home-cooked meals, every moment celebrates simple pleasures and genuine hospitality.
Highlights include:
- Deluxe accommodations at the Blue Gate Garden Inn
- Dinner and a live performance at the famous Blue Gate Theatre
- Hands-on basket-making workshop at Teaberry Wood Products
- A visit to Yoder Popcorn for samples and stories from a local family business
- Shopping and lunch in Shipshewana’s quaint downtown and the Davis Mercantile Mall
- A guided cultural experience at the Menno-Hof Interpretive Center
- Dinner in an authentic Amish home—complete with homemade noodles and pie
- A full day at the legendary Shipshewana Flea Market
- A behind-the-scenes tour and chuckwagon lunch at Cook’s Bison Ranch
Get your tickets HERE
Oct 4-9: Branson or Bust
Join us for six unforgettable days as we travel from Wisconsin to beautiful Branson, Missouri during one of the most stunning times of year in the Ozarks. This fall getaway combines incredible live entertainment, breathtaking scenery, delicious dining, and some of Branson’s most iconic attractions.
Your adventure begins with overnight stops in St. Louis and Vandalia, making travel comfortable and relaxed. Once in Branson, enjoy three nights on the famous Strip while experiencing top attractions including the patriotic Spirit of America show, an exclusive Pink Jeep Lakes & Landmarks tour, Big Cedar Lodge, Dogwood Canyon Nature Park, Silver Dollar City’s spectacular fall festival, and the festive Haygoods Christmas Extravaganza.
You’ll also enjoy memorable dining experiences like the student-prepared farm-to-table meal at The Keeter Center and scenic meals surrounded by Ozark beauty.
Tour Highlights:
- Three nights in Branson
- Spirit of America live show
- Big Cedar Lodge lunch
- Pink Jeep off-road adventure
- Cave Trail Cart Tour
- Ancient Ozarks Natural History Museum
- Keeter Center dinner
- Dogwood Canyon tram tour
- Silver Dollar City Fall Festival
- Haygoods Christmas Extravaganza
- Multiple included meals
- Comfortable motorcoach transportation
This carefully planned tour offers the perfect mix of entertainment, adventure, history, and seasonal charm—making it an ideal fall escape for travelers looking to experience the very best of Branson.