Day 1 – Home to Ashland, WI
Today as we make our way north to majestic Lake Superior. Our first stop will be to enjoy an included lunch in Superior at Barkers Waterfront Grille before stopping at another local favorite, Sweeden Sweets, a small family-owned business that grew out of their love of home-made chocolates. Often, one can see fudges and chocolates being made in their kitchen through the giant windows. We will be treated to their delicious ice cream! You may wish to purchase an additional treat to savor later from their wide selection of goodies. Next, we’ll step back into the Golden Age of railroading as we find our first class seats in the luxury dome car aboard the North Shore Scenic Railroad! Imagine sitting high above the rails, under a dome of curved glass, as the panorama of Lake Superior, Duluth’s pictured hillside and the majestic Northwoods passes all around us! Then we check into the BW The Hotel Chequamegon in Ashland for the next 3 nights. Situated right on Chequamegon Bay, an inlet of Lake Superior, be sure to take in the picturesque view from your lakefront room! Our welcome dinner will be a great time to meet all our fellow travelers.
Included Meals: Lunch, Dinner
Hotel: Best Western The Hotel Chequamegon (3 Nights) (Lakeside Rooms!)
Day 2 – Madeline Island, WI
A wonderful breakfast is served this morning at the hotel. Then our coach will be ferried to the only developed Apostle Island: Madeline Island, where sandy shores and magnificent lake air beckons! Upon landing, we will be met by a knowledgeable step-on guide for a wonderful Madeline Island experience. We’ll tour the village of LaPointe, we’ll browse through the historic Woods Hall Craft Shop (famous for its hand-woven rugs) and other unique gift shops, and we’ll discover 300 years of colorful island history at the Madeline Island Museum. Enjoy a delicious included lunch at one of the Island’s delightful restaurants. We’ll also visit the historic and unique Catholic Mission Cemetery, with graves dating back to the 1700s. There will be an opportunity to take a half mile hike along the beautiful Lake Superior shoreline. We will then return to our hotel before going to dinner at the Deepwater Grille. There is a nice walking path along the lake that you can access right from our hotel.
Included Meals: Breakfast, Lunch, Dinner
Day 3 – Bayfield, WI
A wonderful breakfast will start our day before we enjoy a guided city tour of Bayfield. Bayfield is known as one of the Best Coastal Small Towns, Wisconsin’s Smallest City, the Berry Capital of the State, and the Gateway to the Apostle Islands. The list goes on from there! Bayfield holds many distinctions, but underneath all the titles and accolades, it is also simply and strikingly beautiful. A small city on the shores of the Big Lake. Lunch today is on your own to choose from one of the many Bayfield restaurants. Enjoy some shopping time before we head to the Bayfield Winery. This family-owned and operated winery welcomes us to their beautiful little piece of earth right outside of Bayfield. We will be given a tour, enjoy tastings, and even learn about pairing wines with cheeses. After the winery, we will make our way back to Ashland for a mural tour with our step-on guide. The eight-block Main Street business district, listed on the National Register of Historic Places, is the background for a fascinating walk through Ashland’s history as seen through the eyes of Ashland’s two mural artists. We’ll partake in a wonderful farewell dinner this evening.
Included Meals: Breakfast, Dinner
Day 4 – Ashland to Home
Perhaps you’d like to take one last scenic walk along Chequamegon Bay before our breakfast will be served. As we make our way home, we will stop to enjoy a great ride on the Wisconsin Great Northern Railroad. There’s no better way to experience the beautiful north woods of Wisconsin than by taking a scenic train ride! We will be aboard the pizza train, which is one of their most popular train rides. Our ride lasts about two hours, during which we will see farm fields, deep woods, the scenic Namekagon River, and experience a stop at the Bean Creek Trestle. What a wonderful tour of many new experiences – Lakeside Retreat & Railways, you’ve been good to us!
Included Meals: Breakfast, Lunch
Motorcoach Per Person Pricing Information
Motorcoach Travel Protection Per Person
Travel Bucks
Deposit Due
Passport Needed
Tour Pace
Price Includes
9 Meals, Hotels & Activities as stated in brochure, Luxury Motorcoach
06/08/2025 06/11/2025
Tour Map
Tour Highlights
* 3 Nights in Lakeside Rooms at The Hotel Chequamegon
* North Shore Scenic Railroad Ride
* Madeline Island Tour
* Bayfield City Tour
* Bayfield Winery Tour & Tasting
* Ashland Mural Tour
* Wisconsin Great Northern Railroad Ride
