Day 1 – Home to Ashland, WI
Our scenic North Shore adventure begins with a delightful lunch in Superior at Barkers Waterfront Grille. Our next stop is at the Lake Superior & Mississippi Railroad Co. All aboard the Duluth River Train for a 6-mile rail journey along the scenic St. Louis River. You may wish to visit the open-air car to capture the sights with your camera and to watch a second locomotive being coupled to the train to pull us back to the depot. Then we head to another local favorite, Sweeden Sweets, a small family-owned business that grew out of their love of home-made chocolates. Often, one can see fudge and chocolates being made in their kitchen through the giant windows. Our sweet cravings will be satisfied with a delicious treat! You may wish to purchase an additional treat to savor later from their wide selection of goodies. Then we check into 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, Treat
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 drive around the island, seeing the historic and unique Catholic Mission Cemetery, with graves dating back to the 1700s. Stopping at Big Bay State Park, we’ll take a scenic walk down to the beach. Enjoy a delicious lunch at one of the Island’s delightful restaurants. We’ll tour the village of LaPointe, stopping at St. John’s Church and browsing through the historic Woods Hall Craft Shop (famous for its hand-woven rugs) and other unique gift shops. We’ll also visit the Madeline Island Heritage Center. Then, enjoy free time for shopping & relaxing on the island. Afterwards, 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 heaven right outside of Bayfield. We will be given a tour, enjoy tastings, and learn about pairing wines with cheeses. After the winery, we will make our way back to Ashland for a mural tour with our local 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 & Treat, Hotels & Activities as stated in brochure, Luxury Motorcoach
09/13/2026 09/16/2026
Tour Map
Tour Highlights
* 3 Nights in Lakeside Rooms at The Hotel Chequamegon
* Lake Superior & Mississippi Railroad Co. Train Ride
* Madeline Island Tour
* Bayfield City Tour
* Bayfield Winery Tour & Tasting
* Ashland Mural Tour
* Wisconsin Great Northern Railroad Ride
