Three Days on the Great River Road: Leisure Group Travel’s Winona Itinerary Has It All

Looking for a group trip that pairs Mississippi River scenery with small-town charm? A recent itinerary from Leisure Group Travel lays out the perfect three-day escape to Winona, Minnesota — a river city framed by dramatic bluffs, historic architecture, and enough local flavor to fill a full weekend. Here’s the rundown.

Day 1: Art, Architecture, and Bluff-Top Dining

The trip kicks off at the Minnesota Marine Art Museum, where docent-led tours walk visitors through six galleries of water-inspired art — an easy, engaging stop right off the highway.

From there, groups can settle into one of two home-base options: Winona’s east side, where nearly half a dozen hotels sit within a mile of each other (with complimentary breakfast and bluff views included), or the historic downtown riverfront, putting travelers steps from local shops, restaurants, and galleries.

The afternoon turns into a walking history lesson courtesy of the Winona County Historical Society, which guides visitors through 13 blocks of downtown listed on the National Register of Historic Places. Highlights include the stained-glass details of WNB Financial and Merchants Bank — and, inside WNB Financial, an unexpected display of antique artifacts including an old gun collection and African safari trophies from the bank’s founders. Nearby, Watkins General Store & Museum celebrates the century-and-a-half legacy of the hometown Watkins brand.

Day one wraps with dinner at Signatures Restaurant, where bluff views meet a menu of locally inspired dishes — plus a quirky collection of signed memorabilia scattered throughout the dining room (keep an eye out for a surprise Elvis reference). For groups who want to keep the evening going, a private mixology class caps things off with hands-on cocktail lessons.

Day 2: Eagles, Stained Glass, and a Toy Store for the Ages

Day two heads about 30 minutes down the river to the National Eagle Center in Wabasha, home to live Bald Eagles on daily exhibit and naturalist-led programs designed for group visits.

Nearby in Kellogg, LARK Toys offers a playful detour — a hand-carved carousel, 18-hole mini golf course, café, bookstore, and even a few resident llamas. It’s a nostalgic stop with something for every generation, right down to the housemade fudge.

In the late afternoon, groups get a rare behind-the-scenes look at Willet Stained Glass Studio, one of North America’s largest stained glass studios. Originally founded in 1946 to restore windows damaged in World War II, the studio’s work now appears in more than 15,000 buildings worldwide, including Washington D.C.’s National Cathedral. Watching artists take a glass panel from concept to completion makes for a genuinely unique group experience.

Dinner at River City Grill rounds out the day with a relaxed, locally inspired menu. For groups looking for a scenic alternative, a coach ride up to Garvin Heights Overlook delivers sweeping 500-foot views over the river valley and the Driftless Region’s signature bluffs — a can’t-miss photo stop.

Day 3: River Cruising, Vintage Cars, and Winona’s Famous Donuts

The final day starts with a private tour of the Remlinger Collector Car Museum, where owner Jim Remlinger shares stories from the Midwest’s drag racing heritage alongside a collection of vintage race cars, go-karts, and antique bicycles.

After a casual lunch at Wellington’s Pub & Grill, the trip builds to its signature experience: a cruise on the Winona Tour Boat, led by Captain Aaron and his son and co-captain, River. Guests hear stories of the Upper Mississippi River Valley while spotting bald eagles, turtles, and beavers along the way — plus a pass by Winona’s distinctive boathouse community, a slice of living river culture found almost nowhere else.

No trip to Winona is complete without a stop at Bloedow Bakery, serving handmade donuts and pastries since 1924 — the perfect sweet send-off before hitting the road home.

Good to Know for Group Planners

• Motorcoach parking is free throughout Winona.
• Best photo ops: Garvin Heights City Park (575 feet above the river, with postcard views of the city and Lake Winona) and Sugar Loaf Bluff, best photographed from the shore of Lake Winona or the Highway 43 bridge.
• Ideal groups: Active adult travelers, women’s travel groups, and cultural/heritage travelers.
• Best time to go: Fall foliage season is peak, and bookings should be made 3–6 months out.

Between world-class art, hands-on history, an up-close eagle encounter, and a river cruise past a one-of-a-kind boathouse village, this three-day Winona itinerary hits an impressive range of interests without ever feeling rushed. It’s a Great River Road stop that rewards travelers who want more than just a scenic drive-through.