Tip of Door County with Washington Island across Death's Door Strait
This is another in the series about the top 10 best bareboat charter destination in the U.S.
Two roads diverged in a wood, and I—
I took the one less traveled by,
And that has made all the difference.
From The Road Not Taken by Robert Frost
There are two well-cruised bareboat charter destinations on the Great Lakes in Michigan and Wisconsin: the Apostle Islands in Wisconsin’s Lake Superior, and Grand Traverse Bay in northeastern Lake Michigan. Both have near perfect summer weather, a few islands, a half-dozen towns to explore, sandy beaches, and colorful history. Both destinations also have large fleets of boats available for bareboat charter.
And both of those two destinations can be, well, a little boring.
Then there is Door County. It is a favorite destination of Lake Michigan sailors who own their own boats. Money Magazine named Door County one of the top ten vacation destinations in the U.S. 
The Door Peninsula is a spectacular, 80 mile long finger of limestone between Green Bay and Lake Michigan on the east shore of Wisconsin. It has 250 mi. of shoreline carved out by glacial action. The peninsula is part of the Niagara Escarpment, a rugged backbone arching all the way through Canada over 900 mi. to Niagara Falls. The peninsula has rocky limestone cliffs with more than 30 caves, dunes, sandy beaches, dense forests, and marshy bays. It has the most lighthouses of any county in the nation, five scenic state parks, and 200 shipwrecks..jpg)
Door County’s quaint, picturesque, and cozy villages have retained their historic charm. There are festivals almost every weekend, from the cherry and apple blooms in May to the fall colors in October. Fishing here is world class: the bottom structure and shoreline are diverse and rife with Chinook salmon, lake trout, walleye pike, northern pike, white fish, bass, and perch. Lake Michigan, with its clear, blue, fresh water surrounding the peninsula, is referred to as a “sweet water sea”. Adventure is everywhere, from generally calm bays and coves in the warmer waters on the Green Bay side, to ice cold six foot breakers in spring and fall on the Lake Michigan side.
For bareboat charters Door County is a road less traveled by. It was not always that way. Several years ago there were bareboat charter companies with sizeable fleets serving Door County, but they have closed down, blaming the difficulty of navigating the rocky shoreline of Door County and among its many islands. The strait out of Green Bay to Door County’s Washington Island is named Death’s Door, and is home to some of the 200 shipwrecks noted above. 
Yet there are bareboats available from small operators, and, if you are a reasonably adept and experienced skipper you will have no problem. Modern navigation charts and GPS systems, included with bareboats, have tamed the notorious coastline. Stay out of water with a depth of less than 8 feet, except in marked harbors, and you will never ground. Jackson Harbor, on Washington Island, is one of the safest and most picturesque harbors in North America.
Here are the outfits offering bareboat charters for Door County, click their names to navigate to their web sites.
Lifebreeze Charters, in Sturgeon Bay, has a 40-foot Hunter 41 sloop; Sailboats Inc., in Manitowoc, has a 32-foot C&C; Boat Door County, in Sturgeon Bay, a 26’ McGregor and a 27’ C & C.
Part Two of this article describes some itineraries for cruises of a few days to a few weeks in the waters around Door County.
(Frank Durham, Territory Manager for Medart Marine, and a 35-year veteran of the boating industry in the Great Lakes area, contributed both research and writing to this article.)
(Photo Credits: Door County Visitors Bureau,Starchart Media,James Jordan)
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