How to Plan a Business Retreat to Door County

Just a brief drive away from the big cities of Milwaukee, Madison, and Chicago is the quiet and peaceful peninsula of Door County, the perfect place to get away for your next business retreat, conference, or group tour! Getting out of the office and experiencing something new can inspire and motivate your team members, and Door County is one of the best places to relax, rejuvenate, and ruminate. Check out our guide for planning the best business retreat in Door County for you and your attendees.

Be Prepared

Planning is everything when it comes to a destination event or meeting! To ensure that everything goes smoothly, start with the basics. For instance, consider the group size. Will this be a small affair, such as with one or two departments, or is this for all staff to attend? Will their families or significant others be invited? Determining the group size will help you figure out later logistics such as activities, meals, and lodging options.

Once you’ve learned who will be attending your retreat, consider the goals, needs, and desired activities of your group. Ask yourself what you hope to achieve with the retreat, whether it’s team building, strategic planning, relaxation, or something different. Thinking of your attendees, find out what their interests and activity levels are. For example, if your group typically enjoys going out to nice restaurants or perusing goods in local shops, they might not be interested in a day-long hike in a state park. Alternatively, if your group is outdoorsy, they might want to partake in a hiking, biking, and kayaking tour instead of a tour around a winery or distillery.

All About the Details

Don’t skip the small stuff! Transportation and group meals are some of the most important considerations for your event, and you might not know where to start in a small community like Door County. Luckily, a local event planner is always available to offer advice and guidance from their depth of knowledge of the area. At the Landmark Resort, our experienced sales team is always happy to help when it comes to catering options and coordinating transportation around the peninsula, as well as answering any questions you may have about the seasons, locations, and things to do.

When it comes to the timing of your retreat, the right time of year is paramount to the success of your event and the enjoyment of your guests. In Door County, the most popular times to visit are the summer and fall, and for good reason! Summer offers the most favorable weather conditions, with sunny skies and flourishing fauna, and there is no shortage of outdoor activities to do, from hiking and biking the trails to kayaking Lake Michigan to taking a sunset tour to the many lighthouses on the shoreline. As the weather cools in the fall, the green leaves turn into brilliant shades of gold, orange, and burgundy, and the county comes alive with different harvest festivals on almost every weekend!

Spring and winter are far less busy than summer and fall, but that means it’s less crowded and much quieter and more peaceful. With sparkling snow on the ground, you can venture through the parks on snowshoes or skis or go ice-skating on the rinks. If you and your group would rather stay warm inside, there are several indoor activities to enjoy, like arts and crafts at a local studio, shopping, or dining at local restaurants.

Location is also vital for your destination meeting or event. Consider which towns you and your attendees want to visit while you’re in Door County—do you want to wander Sturgeon Bay’s historic downtown, explore the dining scene in Egg Harbor, shop the local boutiques in Fish Creek, or spend time on the water in Sister Bay? Pick a central location on the peninsula to host your retreat so you don’t have to travel very far to experience the best of what Door County has to offer.

To make planning your event easier on yourself, find a lodging option that also has plenty of event space, so all your group meals and planned activities can happen in one place. Along with nine spacious meeting rooms, the Landmark Resort features nearly 300 comfortable suites, each fitted with a furnished living room, dining area, a kitchen stocked with cooking supplies, a balcony or patio, and free WiFi. When you’re not out exploring Door County, you can have fun where you’re staying! During the summer, we have two heated outdoor pools overlooking the bay, open till sunset for an exquisite view. When the weather gets cold or cloudy, splash into our indoor pool open 24/7. Each lodging building features its own hot tub and sauna, so you can relax at the end of a long day at your convenience. Play games of tennis, pickleball, and shuffleboard with your friends, with free equipment available at the front desk!

With just under nine thousand square feet of meeting space, the Landmark Resort can accommodate your event, large or small. Gather with your attendees for a strategy session, team-building activities, or a group meal without leaving the resort! Our on-site catering team will provide delicious meals for breakfast, lunch, and dinner, alongside snacks, hors d’oeuvres, and desserts to savor. Our sales team will help you put together the perfect destination meeting and group meals without any of the hassle!

Have Fun!

When it comes to planning your group activities, try to have a mix to appeal to everybody’s interests, and plan accordingly so you can make the most of your day. Not sure where to start? Destination Door County has a variety of sample themed itineraries that you can follow, or you can mix and match to create your own!

Immerse yourself in the beauty and tranquility of Door County’s nature with kayaking tours on Lake Michigan. You don’t need to worry if you haven’t kayaked before; the local guides will give quick lessons on how to navigate your vessel, and you can choose between a solo kayak or a tandem one if you require assistance paddling. These tours will take you along the edge of the peninsula, through the underwater caves of Cave Point County Park, and near the sandy beaches of Whitefish Dunes State Park. If you take a shipwreck tour, your kayaks will have a glass bottom, so you can see some of the submerged ships that have sunk in Death’s Door!

If your group would prefer an easy sightseeing tour, the sunset boat tours around Peninsula State Park can’t be beat. Listen to live music as you glide out of the harbor and towards Wisconsin’s most scenic state park, watching the rippling water reflect the sun’s glowing rays. This is a perfect opportunity to capture memories on camera, especially when the boat sails right up underneath Eagle Bluff Lighthouse!

Meals are another great avenue for team building and camaraderie. The local food experience is a great way to explore Door County as well as get to know each other better; talk and laugh over wine flights at one of the many local wineries, have a backstage tour of the brewing and distilling processes, or make reservations for one of the peninsula’s renowned supper clubs. Engage in classic Wisconsin traditions like fish fries and brandy old fashioneds with a breathtaking view of the water, and sample some of the local cuisine, like freshly caught whitefish, homegrown cherries, and even Washington Island lavender-infused drinks!

While your group is visiting Door County, participate in some of the local experiences and traditions. Plan your destination retreat around local festivals, such as Sister Bay’s Fall Fest or Sturgeon Bay’s Fire & Ice Festival, or performances at the local theaters. Door Community Auditorium hosts concerts all year round, drawing acclaimed talent from all over the country! Visit one of the outdoor summer theaters, like Peninsula Players Theatre or Northern Sky Theater, for professional musicals and plays, often set in Wisconsin! Learn more about Door County’s maritime history and take a nautical tour at the Door County Maritime Museum, one of the most influential and educational tourism destinations in northeast Wisconsin.

Important Considerations

While it is important to plan ahead and have fun, there are other variables to consider to make sure that your destination retreat goes off without a hitch. Remember to consider your budget: allocate resources for lodging, food, activities, transportation, and event planning. If you bundle your lodging, meeting space, and catering with the Landmark Resort, you can save more funds for fun Door County activities and adventures!

Keep accessibility in mind as well. You want to include your attendees in as many activities as you can, which is why you should schedule those that most interest them and are considerate of their abilities. For those with mobility issues, a long hike might not be ideal, though the 850-foot canopy ramp up Peninsula State Park’s Eagle Tower is ADA accessible and offers an unparalleled view of Lake Michigan, the surrounding islands, and even the village of Ephraim.

Finally, always remember to communicate! Communicate openly and frequently with your group participants about their lodging, mealtimes, transportation options, and activity schedule, so everyone is always ready and on the same page. Likewise, keep in consistent contact with your event planner, such as if there are any dietary restrictions for catering, if there are going to be any late check-ins or check-outs, and of any possible schedule changes. Constant and transparent communication will go a long way in helping your event transpire seamlessly, as well as ensuring your guests have an amazing time that will keep them coming back!

Ready to start planning your business retreat to Door County for an exceptional experience that you and your guests won’t forget? We’re happy to work with you! Call our sales team today or fill out this form to take the first step in the event planning process!