Adventure Sailing Trips In Bayfield, Wisconsin

Apostle Islands and Bayfield Activities - Rainbow over Bayfield HarborThe sailing season is in full swing, and we’ve seen some beautiful boats out on the bay and in the harbors. Bayfield is the Gateway to the Apostle Islands National Lakeshore on Lake Superior, and many sailing enthusiasts consider the area to have some of the best sailing and recreational boating opportunities in the world.

As you spend time on this body of water, you’ll enjoy breathtaking views of the mainland and islands. Bayfield is particularly picturesque when viewed from a boat! Along with rising brownstone bluffs covered in conifers and hardwoods stands, you’ll see historic lighthouses, and spectacular sunsets. You might even find a shipwreck or two!

Bayfield is a part-time home to many sailors who dock their boats here in one of the harbors. But what if you are just visiting and want to sail the Apostles? Old Rittenhouse Inn’s guests have several options for adventure sailing trips, and most are located just blocks away at the City Dock located at the bottom of Rittenhouse Avenue.

Apostle Islands and Bayfield Activities -SailingOur friends at Dreamcatcher Sailing have 4 boats in their fleet, with 3 located at the City Dock, and one docked in Cornucopia. On the morning trip, the Island Landing Excursion, sail out then explore an island by dinghy from 9:30am to 2:00pm. There’s also an Afternoon Sail from 2:30 to 4:45pm, and a Sea Caves by Sail package that departs from Cornucopia and takes you to the famous mainland sea caves, which you can explore by dinghy. Visit Dreamcatcher Sailing online or call 800-682-1587 for information and reservations.

Another sailing charter we recommend is Animaashi (Ojibwe word meaning: to Sail Away). Your captain is a 1993 U.S. Coast Guard Retired Chief Petty Officer, and he truly knows the ropes of sailing on Lake Superior! Learn the ropes if you’re adventurous, or just relax and enjoy the sights.

Apostle Islands and Bayfield Activities - SailingMany of our guests have taken the opportunity to learn to sail with Superior Charters & Yacht Sales and received bareboat sailing charter certification in as little as two days! For this adventure with one of the best sailing schools, the sailboat is your classroom and also your overnight lodging! Hint: our guests like to “sandwich” the sailing school between a couple of nights at their favorite room at Old Rittenhouse Inn!

Below are options for Bayfield Sailing Charters and Boat Charters from the Bayfield Chamber, and don’t forget to make your lodging reservations soon! Summer is filling fast, and there’s nothing like returning to your room at the Inn and having a nice dinner after a day of sailing!

Adventures Ahoy Sailboat Charters
Animaashi Sailing Company
Dreamcatcher Sailing
PMG Charters LLCManitou Classic Sailing Charters
Sailboats Inc.
Superior Charters & Yacht Sales