4 Iconic Locations for Executive Retreats

By Sara Karnish | Photo: The Osthoff Resort

Having gained momentum post-COVID, companies have begun to return to prioritizing in-person collaboration for leadership teams with high-value executive retreats. In fact, according to American Express Meetings & Events, corporate offsite bookings for small leadership groups increased by 35% from 2021 to 2023, with a focus on non-traditional venues like boutique resorts and nature lodges. This momentum is only expected to continue in 2025.

Managers and team leaders book executive retreats as a way to relax, recharge and bring new energy back to their workplaces. The best retreats can give guests a restoring sense of calm while keeping them rejuvenated through a myriad of activities and amenities.

There are plenty of options for executive retreats in Wisconsin. Whether a team is looking to do it all or get away from it all, there are venues around the state for every need. Check out these four iconic options that specialize in creating unique experiences for small groups among unique Wisconsin backdrops

Central Wisconsin

The Osthoff Resort, Elkhart Lake

The Osthoff Resort is a striking AAA Four Diamond Resort. The venue includes 240 beautifully furnished rooms, multiple dining options and a host of activities, as well as being steps away from a beautiful lakefront. The resort is centrally located, perfect for organizations in Wisconsin and northern Illinois, convenient to Milwaukee, Appleton, Green Bay, Madison and Chicago.

Facilities: The venue offers 38,000 square feet of flexible, functional space, including the 10,000-square-foot Grand Libelle Ballroom. Though perfect for large gatherings, smaller groups have found the resort ideal for their needs. “For executive retreats, our smaller spaces are the most popular,” says Tracie Toth, Director of Sales. “Some groups like a board room or a spacious U-shape setup with A/V at the front; others prefer soft seating to foster creativity, which we offer in our beautifully appointed parlors.” She adds groups like the venue’s Crystal Lake Room, as it can be divided into two halves — meet on one side, eat on the other.

Activities: Collaboration is key for executives, and the Osthoff has a variety of team-building options available, including its popular cooking school. “It makes for a perfect dinner activity to bring your team together,” Toth says. When group members are ready to unwind and relax, the resort’s destination spa has a full menu of services. “Your team can find their Zen and meet up in our lovely Concourse Restaurant for dinner afterward,” she added.

What sets it apart: “We understand your objectives and provide a relaxing, luxurious environment that fosters creativity and collaboration,” Toth says. The resort has a full A/V system and an on-site A/V professional to assist with sound and lighting setup and execution. “Our groups tell us repeatedly that we make their planning easy, and our friendly employees, who genuinely care, make the difference,” Toth says.

Western Wisconsin

Sundara Inn and Spa, Wisconsin Dells

Wellness and well-being are the goals of Sundara Inn and Spa. This adults-only venue is an ideal location for an executive retreat that gives new meaning to the idea of “connection.” “We’re not your typical conference space — even though you’re connecting, you’re connecting to reset, reconnect and recharge through a shared experience,” says General Manager Alyssa Mullin.

Facilities: Mullin describes the venue as “intimate by design.” “Everything is very customizable — from the dining to the spaces.” With just 44 guest units and an off-site villa suite, Sundara’s intimate setting lends itself to brainstorming and unwinding. The resort has a pool package for executive retreats and Mullin said many groups take advantage of the immersive food and beverage packages. Meeting spaces include Mandala A & B, two recently-added rooms offering an additional 1,500 square feet and the Woodland Reflection Room, a more private, non-traditional space almost completely surrounded by the pines.

Activities: Sundara’s strong focus on wellness and wellbeing is evident in available activities and programs. Overnight guests have unlimited access to the resort’s amenities, including pools, a relaxation lounge, an oasis with beverage service, outdoor saltwater pool and hiking trails. Mullin notes there are “robust wellness offerings all our guests are welcome to participate in. We can completely cus- tomize those classes to their liking or the needs of the group.”

What sets it apart: The venue’s smaller size makes it extremely versatile when it comes to programming or logistics like room setups. “We are a smaller facility, so we are really great for those executive-type retreats,” Mullin says. Sundara’s size does not lend itself to an event expecting to draw thousands of attendees. The resort is truly a peaceful retreat where business executives and team leaders can brainstorm and recharge in a natural setting. It does have some A/V capabilities, such as a standard microphone, projector and podium and a full catering menu.

Southern Wisconsin

The Abbey Resort, Fontana

The Abbey was designed as a luxury retreat space for guests. Its unique A-frame gives it a striking appearance — and it’s considered the tallest A-frame in North America, according to General Manager Dan Dolan. The venue hosts more than 400 events — approximately 250 of which are meetings with less than 30 people. Groups have found that The Abbey offers the best of both worlds — business and relaxation. “People want to be in the meeting when they’re in the meeting. When they’re done, they want a venue that’s about relaxing,” Dolan says.

Facilities: Approximately 50% of the venue’s business mix comes from groups. “The reason people come to a smaller venue is because they want to go to a location unlike an airport setting or conference center to get in the right mindset to deliver the content,” Dolan says. With 40,000 square feet of flexible indoor/out- door meeting space, a conference center with 6,000 square feet of meeting space (with natural lighting in some areas), 334 lakehouse-inspired guest rooms, including 13 suites and customizable catering and meeting packages, The Abbey is primed to meet any group’s needs.

Activities: The resort has a full-time activities department with a repository of more than 100 team building activities — some purposeful and intentional; some meant to break the ice and have fun. The scavenger hunt throughout the Village of Fontana and the Geneva Lake Sailing School, a hands-on boat building activity, are favor- ites.

What sets it apart: “We have gorgeous views. Groups really like this setting for events like wine dinners, a tasting dinner or a smaller dinner with entertainment. Our building really sets us apart from other venues,” Dolan says.

Eastern Wisconsin

The American Club, Kohler

The Village of Kohler was founded as a model company town in 1900 when the Kohler company built a new plant. The American Club dates to 1918 and originally housed Kohler’s immigrant workers. Today, the club has earned a Five-Diamond distinction from AAA, is a member of Historic Hotels of America and continues a legacy of old-fashioned elegance with modern amenities.

Facilities: The American Club offers more than 22,000 square feet of versatile meeting spaces, from intimate board rooms to impressive conference rooms and lush outdoor settings. “Many meetings and corporate events incorporate Kohler’s unique experiences, such as golf outings at Whistling Straits or Blackwolf Run, spa retreats at the Kohler Waters Spa or outdoor activities like fishing, skeet shooting or hiking,” says Robin Jensen, Director, Catering & Events.

Activities: Activities range from relaxation (yoga, treatments at the Kohler Waters Spa, and meditation) to exploration (fine dining experiences and outdoor excursions). Team-building activities such as group cooking classes encourage team members to learn more about each other in a fun, relaxed environment.

What sets it apart: “The charming atmosphere of Kohler, Wisconsin, effortlessly pairs luxurious accommodations with world-class services and unique resort experiences, all centered around exceeding guest expectations that delivers a gracious, memorable, and effective setting for intimate meetings and gatherings,” Jensen says.