Dinner at a Fine Dining Restaurant

Start your date night off right with a romantic dinner at a fine dining establishment in Sheboygan. Enjoy a delicious meal in a cozy atmosphere, perfect for reconnecting and enjoying each other’s company. Some popular choices for fine dining in Sheboygan include Il Ritrovo, Trattoria Stefano, and Black Pig.

Alternative options: Charcoal Inn North, 8th Street Ale Haus, Harry’s Prohibition Bistro

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Stroll Along Lake Michigan

Take a leisurely stroll along the shores of Lake Michigan hand in hand with your partner. Watch the sunset over the water and enjoy the peaceful atmosphere of the beach. It’s a perfect way to unwind and spend quality time together.

Alternative options: Kohler-Andrae State Park, North Point Park, Kiwanis Park

Wine Tasting at a Local Vineyard

For a more laid-back and intimate date night experience, consider wine tasting at a local vineyard in Sheboygan. Sample different varieties of wine and learn about the winemaking process while enjoying the company of your partner. Visit places like Blind Horse Winery or Parallel 44 Vineyard & Winery for a relaxing evening.

Alternative options: The Blind Horse Restaurant & Winery, Vintage Elkhart Lake, Vines & Rushes Winery

Catch a Show at the Stefanie H. Weill Center for the Performing Arts

Experience the arts together by attending a show at the Stefanie H. Weill Center for the Performing Arts. Whether you enjoy music, theater, or dance, there’s something for every couple to enjoy at this historic venue in downtown Sheboygan.

Alternative options: John Michael Kohler Arts Center, Plymouth Arts Center, Acoustic Café

Take a Painting Class Together

Get creative with your partner by taking a painting class together. Unleash your artistic side while sipping on a glass of wine and creating a masterpiece. It’s a fun and unique way to bond and make memories together.

Alternative options: Lakeshore Art Supplies, Plymouth Arts Center, Sheboygan Visual Artists

Play Mini Golf at Harbor Pointe Miniature Golf

Embrace your competitive side with a friendly game of mini golf at Harbor Pointe Miniature Golf. Enjoy the scenic views of Sheboygan while putting your way through the course and having a blast with your partner.

Alternative options: Riverdale Country Club, Point Creek Resort, Ellie’s Mini Golf

Enjoy a Couples Massage at a Spa

Indulge in a relaxing couples massage at a spa in Sheboygan. Unwind and de-stress together while enjoying a pampering session that will leave you both feeling rejuvenated and reconnected.

Alternative options: Lakeview Salon & Spa, The Lakehouse Inn & Spa, Crystal River Inn

Attend a Cooking Class

Cook up some romance by attending a cooking class with your partner. Learn new culinary skills and enjoy a hands-on experience creating delicious dishes together. It’s a fun and interactive way to bond and enjoy a meal together.

Alternative options: Lake Geneva School of Cooking, Kitchens of Kohler, Plant-Based Gourmet

Visit Bookworm Gardens

For a whimsical and enchanting date night experience, visit Bookworm Gardens in Sheboygan. Explore the beautiful outdoor gardens inspired by children’s literature and delight in the magical atmosphere with your partner.

Alternative options: Old Plank Road Trail, Sheboygan Riverwalk, Kohler-Andrae State Park

Have a Picnic at Deland Park

Pack a picnic basket and head to Deland Park for a romantic outdoor dining experience with your partner. Enjoy the scenic views of Lake Michigan while sharing a meal and enjoying each other’s company.

Alternative options: Evergreen Park, Kiwanis Park, Vollrath Park

Wyndy is here to help make your date night planning stress-free by connecting you with trusted and experienced babysitters in Sheboygan. Hire a sitter through Wyndy so you can relax and enjoy a night out with your partner, knowing your kids are in good hands.