All in the Family: Multi-generation Vacation Itinerary

When it comes to family travel, we say “the more the merrier!” Multiple generations taking trips together is a popular option for quality time together. So, grab the kids, call the grandparents, and maybe even ask some cousins to meet you, because who doesn’t love a weekend getaway? Let us help you see the scenarios!

All Together
When you’re all together, you’ll want to do things that are fun for everyone – all ages and abilities. The Kenosha Public Museum is a great place to start since there is a little bit of everything – art, natural history, science, and hands-on areas for kids. Plus, there are amazing views of Lake Michigan. Speaking of Lake Michigan, you might always want to get out on the water. You can go fishing with the Kenosha Charter Boat Association to catch salmon and trout, or enjoy a relaxing ride on a sailboat with Sail Away Charters. If you prefer to stay on land, stroll along the Sculpture Walk at HarborPark to enjoy art and photo opportunities together. Or make your own works of art at Alpaca Art Pottery Painting. You’ll each be able to pick your own piece of pottery and paint it to your own design. The only thing you’ll argue about is who gets to decide where to eat.

Parent Time without Kids
The best part of multi-generational travel is the ability to spend time in different mixed groups. Everyone gets some time to enjoy the things they want. If grandparents or an aunt and uncle can take the kiddos, parents get a break. A day could start with shopping downtown or a visit to one of our farmers markets on a Saturday. You’ll find fresh produce, prepared foods, artisan baked goods, and so much more. Adults can also enjoy a visit to one of our local breweries (Kenosha Brewing Co., Rustic Road Brewing Co., and PUBLIC Craft Brewing Co.). Lunch at a coffee shop or rooftop bar overlooking the water is the perfect date day vibe before strolling along the boardwalk. Perhaps you’ll climb the Southport Lighthouse to add a bit of adventure to your time together – it’s 72 steps to the top, offering magnificent views of Lake Michigan, the Kenosha Area, and even the Chicago skyline on a clear day. Sample flights of vino at Wine Knot, feast on incredible Tuscan-inspire seafood at Tuscany Bistro, share small plates at Twisted Cuisine, or enjoy a Chef’s Table experience at The Apis for dinner. You’ll never want the day to end. 

Grandparents and Kids
Time with your grandkids, or even nieces and nephews, is such a special treat. There is plenty to do to keep everyone occupied and happy. Start with some fun nostalgic activities, like taking a ride on the authentic Electric Streetcar. Kenosha has an entire fleet of streetcars which make a two mile loop around the lakefront. You can be dropped off at the Dinosaur Discovery Museum where you will find the Nation’s largest collection of meat-eating theropods! Won’t the rest of your group be impressed with what you have all learned about the connection between dinosaurs and modern-day birds! And yes, there is a T-Rex! For lunch, enjoy an old fashioned drive-in diner with classic burgers, shakes, and homemade root beer. You can choose between The Spot Drive-In and Big-Star Drive-In. Of course you’ll want to get special treats, so stop by Inner Child Comics & Collectibles. Wrap up the afternoon with an ice cream cone at Scoops Ice Cream & Candy or some specialty popcorns from Sandy’s Popper. You’ll win the award for best family member with ease! 

Parents and Kids
If you’re looking for fun ways to connect with your kiddos and make lasting memories, there are plenty of unique experiences to enjoy in Kenosha. Depending on the season, outdoor adventure is a must. Spring through Fall, you can head to the treetops as a family at Boundless Adventures. This aerial ropes course offers different skill levels and tons of fun for everyone. If you prefer to stay grounded, try renting bikes at Total Cyclery and tour the lakefront on two wheels. If the snow is flying, you’ll want to try snow tubing or skiing at Wilmot Mountain. There are also a number of local parks that are perfect for sledding and snowshoeing as alternatives. Keep your strength up by exploring the iconic Wisconsin Cheese – you’ll definitely have fun sampling the options around town. Another classic family outing is a trip to the ballpark to catch a Kenosha Kingfish game at Simmons Field. There is plenty of family entertainment between innings and you never know when you’ll see that charming mascot, King Elvis! If your crew is feeling creative, you might want to check out Pinot’s Palette to learn to paint together. Different designs are offered, and an instructor guides you through all the steps. Learning a new skill is a fun way to spend time together – see how differently everyone interprets the same work of art. You can always check out Fun 101 for additional ideas to extend your trip, too! 

More Ideas for Adults
Find fun at whatever pace you choose. If you want to get a round of golf in, you'll find that Petrifying Springs and Brighton Dale Links are fabulous courses located in Kenosha County Parks. With options for 9-holes or 18, with or without a cart, you have plenty of ways to customize your day. History buffs will enjoy The Civil War Museum, which includes several galleries that are free to explore. The main exhibit, The Fiery Trial, has a nominal fee and includes one of that nations few 360-degree movie experiences that places views in the center of war time for a life-like history lesson. Supper clubs such as the iconic HobNob and even the German-America House of Gerhard offer hearty meals in style, including retro classics like Warm Spinach Salads, Prime Rib, Old Fashioned cocktails, Baked French onion Soup, and even Grasshopper dessert drinks. Add in art galleries, concert venues, a live theatre production, and perhaps even a symphony performance and you'll have plenty to occupy your time in town. 

Don't forget to use the favorite tool on to build your own itinerary. If you need help planning your trip, you can always contact the team at Visit Kenosha for customized assistance. 

Things to Do


There is plenty to see and do both outdoors and indoors in Kenosha.


Find an array of locally-owned shops, boutiques, galleries and markets with an emphasis on the...