27030 Door County, Wisconsin

Day 1

Day 1: Monday, October 4, 2027
Welcome to Door County

Our Door County adventure begins as we board our comfortable Windstar motorcoach and make our way north into Wisconsin. Sit back, relax and enjoy the scenery as we leave the driving to someone else!
By late afternoon, we’ll arrive in the Door County area and settle into our hotel or resort before heading out for our first taste of this beloved Wisconsin destination.
Tonight, we’ll enjoy a welcome dinner at the Nightingale Supper Club in Sturgeon Bay. The Nightingale has been keeping Wisconsin’s classic supper-club tradition alive since 1913, making it the perfect place to kick off our getaway. Settle in for a delicious meal, get to know your fellow travelers and raise a glass to the adventures waiting for us on the peninsula.
After dinner, we’ll return to our hotel for a relaxing evening.

Day 2

Day 2: Tuesday, October 5, 2027
Lighthouses, Local Flavors & Theatre in the Garden

Enjoy breakfast at the hotel before setting out for a day devoted to some of Door County’s most iconic sights.
This morning, climb aboard a Door County Trolley for a private Lighthouse Tour filled with scenery, history and plenty of personality from our local guide. We’ll travel through Door County’s charming communities and hidden bays while visiting three of the peninsula’s treasured maritime landmarks: Eagle Bluff Lighthouse, Cana Island Lighthouse and the Baileys Harbor Range Lights.
These beacons have long been part of Door County’s maritime story, standing watch over waters that shaped the peninsula’s history. Along the way, enjoy entertaining narration, beautiful views and a delicious included box lunch. It’s the perfect combination of sightseeing and storytelling, with plenty of postcard-worthy scenery along the route.
Later this afternoon, we’ll return to the hotel for a little time to freshen up before an evening in Fish Creek.

Dinner tonight is included at The English Inn, a local favorite with a story all its own. Parts of the building date back to its days as a lumber mill more than a century ago, giving the restaurant plenty of character and old Door County charm. And while you’re there, keep an eye out for their famous Cherry Hot Bacon Dressing, a delicious Door County-inspired twist worth trying!
After dinner, we’re headed to one of the most enchanting theatre settings you’ll find anywhere.
Nestled among fragrant cedar trees along the shores of Green Bay, Peninsula Players Theatre has been entertaining audiences since 1935. Known as the “Theatre in a Garden,” the setting is part of the experience. Before curtain time, enjoy the peaceful shoreline, beautiful grounds and relaxed atmosphere before settling in for an exciting live performance.
It’s an unforgettable way to end a full day in Door County!

Day 3

Day 3: Wednesday, October 6, 2027
Goats on the Roof, Death’s Door & a Door County Tradition

After breakfast, another full day of Door County fun awaits!
Our first stop is Koepsel’s Farm Market in Baileys Harbor, where we’ll enjoy a group tour followed by time to browse and shop. Door County is famous for its local flavors, especially its cherries, and this is a wonderful opportunity to discover jams, preserves, specialty foods and other goodies that make perfect souvenirs from our Wisconsin getaway.
Then we’re off to Sister Bay for lunch at a Door County landmark you may have seen in photographs long before visiting in person: Al Johnson’s Swedish Restaurant.
This authentic Swedish restaurant is instantly recognizable thanks to its remarkable sod-covered roof. And yes, those really are goats grazing on top! It’s one of Door County’s most photographed and talked-about sights, but the Scandinavian atmosphere and delicious lunch make the experience every bit as memorable as the rooftop residents.
After lunch, we’ll head north toward Gills Rock and the waters known as Death’s Door.
This afternoon, step aboard for the Death’s Door Lighthouse Cruise, a scenic journey through some of Door County’s most storied waters. Along the way, we’ll see Plum Island and Pilot Island Lighthouses, take in views toward Washington Island, and hear stories of Door County’s fascinating maritime history, including the shipwrecks and legends associated with this famous passage.
With open water, island scenery, historic lighthouses and tales from the past, this cruise is sure to be one of the highlights of our adventure.
Back on land, we have one more quintessential Door County experience waiting for us: a traditional Door County Fish Boil at the Old Post Office Restaurant in Ephraim.
More than simply dinner, the fish boil is part meal, part tradition and part show! Watch as locally caught Michigan whitefish is prepared outdoors over a roaring open fire. The evening builds toward the famous boil-over, when flames leap dramatically into the air before dinner is served.
It’s rustic, lively and wonderfully Door County. Alternatives to fish will also be available.
After an action-packed day, we’ll return to our hotel for our final evening on the peninsula.

Day 4

Day 4: Thursday, October 7, 2027
One Last Taste of Wisconsin

Enjoy breakfast at the hotel before we say goodbye to Door County and begin our journey home.
But Wisconsin isn’t letting us leave without one last treat!
This afternoon, we’ll stop at Alp & Dell Cheese Store in Monroe, a longtime favorite stop among Windstar Wanderers. Browse an irresistible selection of Wisconsin cheeses and specialty items and pick up a few goodies to take home.
And if we’re lucky, we may even be treated to a little yodeling from the owner. Because really, what better way could there be to wrap up a Wisconsin adventure?
From glowing lighthouses and lakeside villages to goats on the roof, a scenic cruise, live theatre and a fiery fish boil, our Door County getaway delivers four days filled with fun, flavor and experiences you simply can’t find anywhere else.
Come discover why this corner of Wisconsin has a way of turning first-time visitors into lifelong fans!