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Sailing the Apostle Islands | True North Sailing Charters

Sailing adventures from Bayfield, Wisconsin in Apostle Islands National Lakeshore

Bayfield Area Lodging

Looking for a place to stay that’s as memorable as your time on the water? These unique glamping-style lodging options are designed for travelers who love the outdoors and want a deeper connection to nature without giving up comfort.

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Getting there is part of the adventure. Whether you arrive by ferry, hike through the forest, or step aboard a sailboat docked in the heart of Bayfield, each stay offers a one-of-a-kind experience rooted in simplicity, beauty, and exploration. Fall asleep to the sound of waves, wake to birdsong in the woods, or take in Lake Superior views from a bluffside cabin.

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Guests who book both one of these lodging options and a True North Sailing Charters trip receive a 10 percent discount on their stay and on all True North Sailing or Whitecap Kayak adventures. Choose your basecamp and make your stay part of the adventure.

Starling, a 33’ Cheoy Lee Clipper, docked in Bayfield Harbor at sunset with vibrant skies reflecting on the water.

The North Channel Cabin

10% Discount with Sailing Trip

North Channel Cabin

Perched on a scenic bluff overlooking Lake Superior, the North Channel Cabin on Madeline Island offers sweeping views of the Apostle Islands. Accessible by ferry, this secluded island retreat is perfect for couples or small families seeking adventure, island charm, and a deep connection with nature.

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Located just a mile from Big Bay State Park, it’s an ideal base for hiking, paddling, and exploring the islands from your own private escape. Guests who stay here also receive a 10 percent discount on all True North Sailing Charters, Whitecap Kayak Day Trips, as well as the cabin stay.

Sailor Springs Glamping

10% Discount with Sailing Trip

Sailor Springs Glamping Cabin

     Tucked into the woods just two miles from downtown Bayfield and the marina, Sailor Springs offers an adventurous hike-in glamping experience.

 

     Enjoy the comforts of a furnished tent, a campfire under the stars, and the sounds of nature all around. It’s the perfect basecamp for sailing, hiking, and exploring the Bayfield area and Apostle Islands.

Stay Aboard Starling

Starling

     Turn your sailing trip into a one-of-a-kind overnight stay aboard Starling, docked right in the heart of Bayfield at the city marina. Book a Bayfield Adventure Sail, then check into the boat the evening before your trip and spend the night on the water. Watch the sunset, enjoy dinner in town, and fall asleep to the gentle motion of the harbor.

 

This is a “glamping-style” experience—Starling has power, a small galley, and cozy sleeping space for up to four guests. Bring your own bedding or sleeping bags and enjoy a unique, floating stay on Lake Superior.

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