Frosty Treats, Cheese Curds, and Burgers in Bed: a Romantic Getaway in Sheboygan

There's a romantic getaway in Sheboygan for every couple, even if it's burgers in bed, frosty treats, and cheese curds, because what else do you need?

I nudged the makeshift vase a couple centimeters to the left, then gently tugged the purple aster so it would be more noticeable in the multi-colored bouquet. Two candles flickered, their flames turning the blue glass bowls nearly translucent.

In the corner, a fire crackled. Well, it didn’t quite crackle since it was a gas fireplace, but it seemed like it should crackle, since that’s what fires do. I eased open the sliding glass door, listening to the waves from Lake Michigan.

Then one final sweep as I arranged the bread from City Bakery, the cheese from Hennings, and the summer sausage from Miesfeld’s.

My phone buzzed. He was here!

I ran outside and paced, waiting impatiently in Blue Harbor Resort’s parking lot. He found a spot and had barely gotten out of the car before I practically tackled him with a gigantic hug and an even bigger kiss.

Our romantic getaway in Sheboygan could begin.

Full disclosure: Visit Sheboygan hosted our stay at Blue Harbor Resort, but all opinions and romantic shenanigans are entirely my own.

DIY Romantic Getaway in Sheboygan

It had only been four days since I’d seen my husband. I’d left on Monday to teach a writing workshop in Sheboygan, Wisconsin. Originally, I would have returned home on Thursday, but when I discovered friends would be getting married that weekend along the north shore, I extended my stay and invited Mr. TLT to join me for a romantic weekend.

We needed one.

It’s not that anything was wrong. We’d been so busy the entire year that we had barely spent time together.

This year alone, we’d traveled to Colorado Springs and Denver. I’d flown to San Diego and drove up the Pacific coast, then took Empire Builder back. Then another western adventure, this time for five weeks, along with other, shorter trips.

When I was home, Jim and I would have a few moments together at lunch, and then an hour or two in the evening, and that was it.

As the owner of The Caroling Connection, a Dickensian caroling company, the last quarter of his year becomes quite hectic. I’d been gone so often, I spent the few weeks I was home catching up and trying to tell the stories of the places I’d seen.

Plus, I had that writing workshop to teach, and it’s intense (to say the least).

A romantic getaway in Sheboygan was exactly what we needed – at least, our version of a romantic weekend.

There’s a connotation associated with that phrase. It implies lavish dinners, breakfast in bed, bubble baths, wine and champagne and chocolates, moonlight sonatas, yada yada yada. 

All that is lovely. But none of it is required. (Except for chocolates. Chocolates are required.)

Jim entered our room. He noticed the flowers in the makeshift vase, a steel-walled coffee mug covered in symbols of Sheboygan.

He noticed the candles. The silver charger they sat on. The fire. The sound of Lake Michigan through the screen door.

Candles and flowers in a makeshift vase with a fire in the background help make for a romantic getaway in Sheboygan

He heard soft jazz emanating from the bluetooth speaker on the table. He couldn’t miss the giant tub for two or the spread of local foods.

He noticed all that, and what he saw was love.

I’d spent the morning shopping, stopping at the dollar store for the candles and the charger, ALDI for the flowers, City Bakery for the bread, and the Sheboygan Visitor Center for the summer sausage. I’d picked up the cheese on my way into town on Monday. All of it had been on sale.

City Bakery mural in Sheboygan

I might have spent twenty dollars on the whole shebang. Romantic gestures don’t need to be fancy, or expensive.

After Jim settled in, we crossed the grass to the shore of Lake Michigan and walked the path, holding hands and stopping to watch surfers.

Waves rolling in from Lake Michigan to rocky shoreline

Frosty treats were next at South Pier Parlor. We bought our one-scoop waffle cones in the delightfully retro-styled ice cream shoppe (complete with model train circumnavigating the interior) and then walked along the Sheboygan River boardwalk.

Seagulls called as we strolled past signs detailing local history, past a miniature golf course that was closed for the season, past a restored tug boat named Islander. The 1936 gill-netter has been a fixture on the waterfront since 1977, and a slew of local organizations supported its restoration.

Flavors you can add to sodas at South Pier Parlor, an old fashioned ice cream shoppe
Ice cream from South Pier Parlor in Sheboygan
The Islander, restored fishing tug boat near the Sheboygan River waterfront

If we were doing a fancy romantic weekend, we might have had dinner at Lino Ristorante Italiano, an authentic Italian restaurant also on South Pier. Instead, we went to On the Rocks Bar and Grill off the hotel lobby, ordered cheese curds and a blackberry old fashioned, and were back in our room by eight. 

Cheese curds from On The Rocks Bar and Grill at Blue Harbor Resort in Sheboygan

The next morning, I woke up and walked to the shore to see the sunrise, as I’d done every day but one since arriving in Sheboygan. I’m an early riser; Jim is not. I treasure my quiet time before the world awakens. It works out well.

After a lovely morning that included a jet-infused bath and more sand between my toes, we drove downtown for a stop at Victorian Chocolate Shoppe.

Sunrise over Lake Michigan with Adirondack chairs on the sand
Bath with candles at Blue Harbor Resort

Inside the old Interurban Station, a streetcar terminal built in 1925, a visit to this boutique is a requirement for any romantic weekend in Sheboygan.

Its nostalgic candy, chocolate creams, and a variety of truffles are a steal: most truffles are a dollar. You can get a dozen chocolate covered cherries for seven. When I commented on how inexpensive they were, the cashier said they’d just raised their prices.

For our next romantic stop, I took Jim to the bathroom.

Wait! Before I lose you, the bathroom happened to be in the John Michael Kohler Arts Center. A contemporary museum in the heart of downtown Sheboygan, its themed bathrooms take immersive art to a whole new level.

I’d seen them before, but I knew Jim would get a kick out of Caesar “Celebrating another conquest” over a well-decorated “throne.” We also enjoyed the bold, unique exhibits in the galleries themselves.

Caesar bathroom stall at John Michael Kohler Arts Center in downtown Sheboygan
Art at John Michael Kohler Arts Center in Sheboygan

We left the museum for the north shore. It was time to crash a wedding. 

(Sort of. The bride saw my Facebook story and realized we were in town and invited us before we could show up unexpectedly.)

The wedding wasn’t your standard elaborate affair. It was intimate. Casual. The parties arrived and as the groom got out of his car in his cargo shorts, he put on a button-down black shirt and a tie. The bride wore a flowing dress of magnolias on a dark background. They married under a gazebo, surrounded by family and friends, on a tailor-made fall day. They connected through music, and his vows were a string of lines from their favorite artists.

Standard? No. Romantic? Yes.

They held their reception at 3 Sheeps Brewing Company. There were wings and brats and a beer-themed cake. He sang to her. (He doesn’t sing.)

Standard? No. Perfect? Hell yes.

Kites on a picture-perfect day in Sheboygan
Beer-themed cake at 3 Sheeps Brewing

We left the newlyweds and stopped for a drink at Harry’s Prohibition Bistro. Its decor reflected its name, complete with a gangster perched in the balcony.

Jim and Theresa outside Harry's Prohibition Bistro on South Pier in Sheboygan

We could have stayed for wood-fired Neopolitan pizza in the speakeasy-themed restaurant, and normally that would have been delightful. But after the workshop and all the travel and the anticipation of Jim’s upcoming season, we wanted something low-key. I knew there was a place more our speed that was even closer to the resort.

I’d been to Anglers Avenue once before and heard they had great burgers, so Jim and I sat at the bar and decided on a couple to go.

I ordered a beer (3 Sheeps, of course) while we waited, and discovered the woman on the corner barstool was the Executive Chef. She told us they’d be open early the next morning because the Green Bay Packers game in London would be televised. We met a couple celebrating their anniversary. Teenagers dressed for Homecoming paraded through. Our burgers arrived and we took them back to our room.

Why have breakfast in bed when you can have burgers in bed?

Burgers in bed ordered to go from Anglers Avenue. Burgers in styrofoam containers with french fries.

Sunday morning. One last sunrise. We took our time packing up and got to Anglers Avenue by ten. Bloody mary with a 3 Sheeps beer back. Breakfast pizza. Packers fans wrapped up in the game and a half-time performance on a whiz-bang contraption. The anniversary couple sat at a table with friends. The chef sat at the end of the bar.

Breakfast pizza at Anglers Avenue in Sheboygan Wisconsin
Packers purse sitting on bar at Anglers Avenue

We ate our breakfast pizza, leaving room for Blast Soft Serve. Multiple people had told us about this spot on the other side of the Sheboygan River, and the Goodriches rarely turn down frosty treats.

We got there a bit early and killed time by walking down to the yacht club, through the lot where the old Armory Building had been. Blast opened. I ordered vanilla with a swirl of black raspberry; he got green apple. We sat on the bench and watched the seagulls and simply enjoyed our time together.

Eating Blast Soft Serve in Sheboygan Wisconsin - woman on left and man on right. She's holding a soft serve cone with purple and his has green. Building in background with lights.

That’s what a romantic weekend is about. It’s not about the flowers and chocolates, although those don’t hurt. It’s not about fancy restaurants or Hallmark Movie expectations.

It’s about two people who love each other, choosing to spend time together, paying attention to each other, and knowing that sometimes a burger to go is the most romantic dinner in the world.

Check rates to create your own DIY romantic getaway at Blue Harbor Resort {affiliate link}

Do not disturb sign on door at Blue Harbor Resort