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Bayfield, WI – The 5 Best Sailing Charters in the Apostle Islands

Shut your eyes, take a deep breath, and imagine – clear blue water. The rise and fall of the waves. The sound of your sailboat gliding through the pristine waters of Lake Superior. You feel the warm sun and a light spray of water on your face as you relax on the bow.

Gaze at old-growth forests. Study century-old lighthouses and sea caves carved out of sandstone. Admire the cozy harbor towns that line the south shore of Lake Superior.

Sailing on the big waters of Lake Superior and the Apostle Islands National Lakeshore is an experience you don’t want to miss.

It’s one thing to enjoy Lake Superior’s views from the mainland. But it’s another to ride on its waters. To feel the wind pushing back your hair. To breathe in its air.

For many, the cost and upkeep of owning a boat are out of reach. The cost of registration, insurance, gas, and more add up quickly. Not to mention the hassle of towing and storing the boat – in both summer and winter.

Plus, it’s one thing to cruise around on a motorized boat and another to sail.

Sailing requires unique skills. There are sails to hoist and helms to man. You must understand wind direction and knot tying – all while learning Lake Superior’s weather patterns, nautical navigation, and boat safety.

It doesn’t make sense to own a boat for many of us whether it’s propelled by wind or gas. But don’t worry, there are still several ways to have a true Lake Superior sailing adventure.

Sailing Trips for Adults, Couples, and Families

Are you looking to sail for a couple of hours at sunset? Spend an entire day on Lake Superior? Or indulge in an overnight excursion? Looking to snuggle with a loved one or have a hands-on sailing adventure? Here are the 5 best charters and sailing experiences to choose from.

  • True North Sailing Charters offers sailing adventures that launch out of the Bayfield Harbor into Chequamegon Bay. Choose from half and full-day excursions that go deep into the Apostle Islands. Their seasoned crew offers hands-on sailing instruction for those wishing to give it a go on their own – and comfort to those wishing to sit back set their eyes on the horizon, and take in the beauty of Lake Superior. Overnight trips are available upon request.
  • All Hands Sailing offers hands-on day and overnight sailing excursions. Sail to an island and hop aboard a dinghy to explore the shorelines, sandstone cliffs, and sea caves. Looking to experience a happy hour like never before? Ask about their popular Happy Hour Cruises.

Learn to Sail on Lake Superior

Looking to take your sailing adventure one step further? Check out these sailing charters that offer classes for beginner to advanced sailors. Or if you’re a captain without a ship sailboat rentals are available.

  • Lake Superior Tall Ships provides “educational excursions and programs aboard their schooner, Abbey Road. Enjoy an “unplugged” adventure as you learn to sail on Lake Superior and unlock a new set of life skills.
  • Superior Charters. Let the sailboat be your classroom and your sleeping quarters while you earn your bareboat certification in as little as 3 days. Not ready to take on the title of sailboat captain? No worries. They offer captained multi-day sailing trips within the Apostle Islands. Can’t find the sailing adventure you’re looking for? Ask for a customized itinerary.
  • Northern Breezes Sailing hosts 3-5 day vacation sailing classes. Learn sailing basics or take part in advanced offshore classes to other destination places in Lake Superior. The American Sailing Association has named Northern Breezes the sailing school of the year!

Blessing of the Fleet

Not ready to stretch your sea legs? Then we invite you to join fishermen, sailors, boaters, and kayakers in the Blessing of the Fleet.

For more than 60 years, boats have paraded through Bayfield’s Harbor to receive a blessing of safe passage and a prosperous season on Lake Superior.

This year’s service is on June 2nd, 2024 at 1 pm. Onlookers can set up camp chairs or find a park bench at Memorial Park in Bayfield to witness this time-honored tradition.

Seagull Bay Is the Perfect Place for Sailors

Whether you set sail for a few hours or a few days, Seagull Bay Lakeside Motel is here to anchor your sailing vacation.

We know how important it is for you to experience Lake Superior up close and personal. Our motel and properties adorn the banks of Lake Superior. You’ll enjoy views of the Apostle Islands from your balcony or the lawn.

Our convenient location gives you easy access to the Brownstone Trail. Here you can take a 10-minute walk to the Bayfield City Dock to meet your captain. Or drive 5 minutes to Pike’s Bay Marina to catch your charter.

We offer a variety of lodging accommodations to fit groups of any size. And our affordable prices ensure that your Bayfield sailing adventure is one you won’t forget.

Come to Bayfield and sail on its “tall waters.” BOOK NOW at Seagull Bay.

Your hosts,

Mollie, Isaac, Axel, Ridge, and Banks.


True North Sailing Charters

All Hands Sailing

Lake Superior Tall Ships

Superior Charters

Northern Breezes Sailing

Blessing of the Fleet – Bayfield

June 26, 2022

Get the Most Out of Your Bayfield, Wisconsin Getaway

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Bayfield is brimming with outdoor adventures, local events, and renowned festivals.

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