Sailboats Inc., SI Marine Management
Sailing Charters
Lake Superior
  Bayfield, Wisconsin
The Apostle Islands have long been a mecca for sailors.  The islands’ protected bays, public docks, pristine beaches, lighthouses and natural beauty offer outstanding boating and sightseeing opportunities.
Lake Michigan
  Chicago, Illinois
Whether you’re interested in a half day retreat or a week long getaway, our downtown location is the place to be!  Experience all that Chicago has to offer while relaxing on the waterfront.
Lake Pepin
  Lake City, Minnesota
Spread between 400 foot wooded bluffs that mark the border between Western Wisconsin and Southeastern Minnesota, Lake Pepin is the only natural lake on the entire Mississippi River system.  This twenty two by three mile wide body of water offers few navigational hazards and abundant anchorages.

Bayfield Charter Fleet      Directions
The Apostle Islands archipelago includes 22 islands and is located in far northwestern Wisconsin, off the Bayfield Peninsula. Twenty-one of these islands, and a 12-mile segment along the shore of Wisconsin’s north coast, comprise the Apostle Islands National Lakeshore. The beauty of the islands are enhanced by the area’s geology. Colorful precambrian sandstone have eroded into interesting cliff formations, including sea caves, and there is a highly diverse collection of sandscapes, including sandspits, cuspate forelands, tombolos, a barrier spit, and numerous beaches. These sandscapes are among the most pristine left in the Great Lakes region. The island’s wildlife includes a diverse population of nesting and migratory birds and a variety of mammals, amphibians, and fish. The rich history of the islands includes Native Americans, voyageurs, loggers, quarrying, farmers and commercial fisherman. The six historic light stations in the park, built to aid Great Lakes navigation, are the largest such group found in any unit of the National Park System.

Useful Links:
National Park Service -
Bayfield Chamber of Commerce -


Chicago Charter Fleet     Directions
Yachts are located on moorings in Monroe Harbor that are accessed by water taxi. These moorings are extremely safe and easy to use. They provide excellent privacy for a tranquil evening aboard your yacht.
Chicago’s stunning skyline surrounds this splendid marina. Buckingham Fountain marks the center channel of the harbor - its colorful lights and huge spray guiding night sailors to port.
Monroe Harbor hosts many of the city's celebrations, including the Independence Day Fireworks, and the Venetian Night Yacht Parade. Monroe Harbor is also a wonderful place for viewing the Chicago Air Show.


Lake City Charter Fleet     Directions     Cruising Guide
Lake City rests on the western shores of Lake Pepin, the widest spot on the Mississippi River.  This is a relaxed river town and is located 65 miles southeast of the Twin Cities (Minneapolis & St. Paul, Minnesota).  Situated among the beautiful scenic river bluffs, Lake City is perfect for those who love the relaxed atmosphere of a small town, the amenities of a big town and the beauty of nature.

Five minutes after untying from the dock at the Lake City Marina, you are out sailing.  Depending on the day and your spirit, you either drift lazily in the sunshine, or blast through frontal winds.  There are plenty of good anchorages, places to explore and largely uncrowded waters.  Lake Pepin offers enjoyment for both beginning and more accomplished sailors.

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For reservation information and specific yacht availability, call: 715-779-3269
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Corporate Office: 117 South 1st Street • Bayfield, WI 54814