Cruising Guide to the Apostle Islands


The Apostle Islands National Lakeshore offers visitors the chance to explore sea caves, tour lighthouses, hike, camp and cruise around 21 islands in the northern portion of Lake Superior in Wisconsin  (published July 2015)

The author at the helm
The author at the helm

Our sailing adventure began at a local diner in our small town in central Illinois. My wife and I were having lunch after church with our friends, Dave and Pam Sorenson, from Duluth, Minnesota. Over the years, Dave would talk about the Apostle Islands on Lake Superior with a sense of awe.  Even now, after his many years of cruising those waters, he still talked about the upcoming season with anticipation. As I listened to his descriptions of the twenty-one beautiful islands, the stunning sea caves, the seven lighthouses, the beautiful island bays, many hiking trails and their favorite spots for picnicking, I was anxiously waiting to tell him the news – we had joined the ranks of cruisers ourselves.

After I announced the news of our new-to-us 1990 MacGregor 26 Classic, our conversation turned to planning a trip for the coming season to sail the Apostle Islands together, along with our sailing friends Steve and Dodie Gomer. We sent Dave and Pam off on their trip home with excitement and anticipation of our adventure.
Apostle Islands
There are a couple of ways to cruise the Apostle Islands. We chose to day-sail, returning to the marina each evening to enjoy the great restaurants in the city of Bayfield or on Madeline Island.  You may choose to sail away from civilization and cruise from island to island, not returning to the marina until your appointed time. No matter which way you choose, as each new day dawns you will have many options available to you. Choosing where to sail or which island to explore is part of the fun. The following are some of the islands we saw in the two weeks we were there.

On our first full day of cruising, we left our home base of Pikes Bay Marina and sailed up the North Channel, bound for Stockton Island. As we sailed northeast, we passed the western coast of Madeline Island.   Madeline Island has a rich and varied history beginning with the Ojibwe Indians. Later, the island became an outpost for French exploration and fur trading. Today, Madeline Island sports a population of 246 permanent residents. Hiking and cycling are popular activities.  Bikes, mopeds, sea kayaks and canoes are available for rent. Big Bay State Park is located on the east-central shoreline. Big Bay Town Park adjoins the state park and offers camping and access to the longest beach on the island.

Sailing further northeast, we passed Basswood and then Hermit Island on our port side.  These islands were heavily quarried for their brownstone in the late Nineteenth and early Twentieth Century. After the great Chicago fire, brownstone from these islands was used in the reconstruction and may still be seen today in the beautiful older buildings in downtown Chicago.

Hermit Island, as it was later named, became home to a hermit named William Wilson after he lost a fight on Madeline Island to another man in 1847. The loser of the fight had agreed to leave Madeline Island forever.  Later, a man named Frederick Prentice, who was in his seventies at the time, brought his 19 year old bride from New York City to live on Hermit Island.  She took one look and immediately headed back to New York, not spending a single night on the island.

Our destination, Stockton Island, appeared ahead on our port side as we sailed past Hermit Island.  Stockton Island, the second largest island in the Apostle Islands, is the most visited of the Apostle Islands, primarily due to its excellent camping, protected bays and beautiful beaches.  Stockton Island’s Presque Isle Bay is a beautiful bay for overnight anchorage.

Cave Rain
Cave Rain

At sunrise, as I stepped out of the cabin and into the cockpit to enjoy my morning cup of coffee, I was treated to the most beautiful sit–a bald eagle swooped down and snatched his breakfast out of the water not twenty feet from me. It was a magnificent start to what was a great day of sailing. We planned to sail from the marina, around the northern tip of Outer Island and back, a distance of approximately 45 miles.

The winds looked good, if not a bit strong for early morning, as we sailed out from Pikes Bay Marina.  Being careful to pass the navigation buoy on our port side, we were making good time as we slid between Madeline Island to our port side and Long Island to our starboard. Turning northeast, we paralleled the east coast of Madeline Island. Sailing northeast via the South Channel, we passed Madeline’s Big Bay, where people enjoyed the day wind surfing, skiing, tubing and swimming.

Along the way, we passed several commercial fishing boats plying their trade. Leaving Madeline Island behind us, we headed toward the lighthouses on the southeastern tip of Michigan Island. Michigan Island has the distinction of having both the first and the last lighthouses built on the Apostle Islands. The first lighthouse was built by mistake. It was originally contracted to be built on Long Island. Since no one wanted to admit the mistake, it was simply left there. It proved to be too small to be seen from the other side of the island so, several years later, a larger lighthouse was built just a few yards from the first.

As we sailed up the eastern side of Michigan Island the wind, which would typically increase as the afternoon approached, went almost dead calm. With no wind to fill our sails, we had no other option than to fire up the motor and continue on. Passing the northeastern tip of Michigan Island, we began scanning to the northwest for Gull Island. As we continued northeast, we finally spotted it. It appeared to be nothing more than a shoal just a few feet above water.

Gull Island is one of two sanctuary islands in the Apostles. Visitors are not allowed on either of those islands, which was fine by us. There is not a single blade of grass on Gull Island.  The entire island is covered in seagull guano. A word of warning: pass well to the east and north of this small island as the water’s depth at this point is in the single digits and boulders  appear just under the surface seemingly out of nowhere.

As we continued to motor northward, Outer Island, our destination, was ahead and to the west.  Our original intention was to sail up the eastern side of the island, circle around the northern tip to see the lighthouse, and then head back down the western side.  Assessing the wind, the distance back to Pikes Bay Marina, and our fuel supply, we made the decision to cut our trip short. It was a wise decision as our fuel was almost completely exhausted by the time we slipped our boat in the marina that night.

Manitou Island fishing camp, a free informative guided tour is available here
Manitou Island fishing camp, a free informative guided tour is available here

Most of our sailing had been day-sailing to that point. We enjoyed our evenings having dinner with our friends at one of the great restaurants in Bayfield. We would spend the remainder of the evening at the marina clubhouse or out on the docks visiting with friends. Now we decided to sail to Sand Island from Pikes Bay Marina, taking time to enjoy some activities on a few of the islands along the way.

We sailed out of Pikes Bay Marina and headed northeast up the West Channel toward Oak Island.  Oak Island is the tallest island of the Apostle Islands at 1,081 feet, approximately 500 hundred feet above the lake.  Along with Basswood Island, Oak Island was heavily harvested for its namesake trees.  Due to the treacherous terrain on this island, many men lost their lives harvesting lumber there.

As we sailed around the northeastern side of Oak Island, we found our first stop, Manitou Island.  This small island once hosted a logging and fishing camp started in the 1890s.  In the 1930s two Norwegian brothers bought the fishing camp and remained there until the 1980s. Each winter, as the lake froze over, they would drive dogsleds out on the ice where they would hang gill nets on lines with poles under the ice. After a few days they would collect their catch of whitefish and trout which they would later sell in the town of Bayfield. The camp still remains exactly as they left it. A free informative guided tour is available there.

Our next stop was Raspberry Island. Raspberry Island lighthouse, the most famous of the seven lighthouses in the Apostle Islands, was the only lighthouse available for touring during that summer.  The other six, 100 year old lighthouses, were being renovated to restore them back to their prime. Guided tours of the Raspberry Island Lighthouse are available for a nominal fee and highly recommended.

Michigan Island Lighthouse
Michigan Island Lighthouse

Leaving Raspberry Island, we headed for Sand Island. Along the way we passed York Island, one of the smaller islands in the Apostle Islands. There are three campsites available on York Island.  Like all the campsites on the Apostle Islands, the amenities are minimal, typically including a vault toilet, fire ring, and a food locker to keep the black bears at bay.

Our destination, Sand Island, is the only island of the Apostles other than Madeline Island to have been previously populated. In the mid-eighteenth century the village of Shaw was established here. Francis Shaw had received his homestead on the island as a bonus for his service during the Civil War. Eventually the population on Sand Island reached 100 people.  They even had their own post office. The town was finally abandoned in 1944.

Other than the lighthouse on the northern end of the island, the main attractions on Sand Island are the amazing sea caves on its shoreline. Formed by ice and wave action over many years, the sea caves are a stunningly beautiful wonderland of pillars and caverns, many of which can be explored via dinghy or sea kayak.

Steve and Dodie Gomer enjoying the beauty of the Apostle Islands
Steve and Dodie Gomer enjoying the beauty of the Apostle Islands

The Apostle Islands are unquestionably among the best cruising areas in the United States.  Where else can you sail to 21unique island, see seven lighthouses, go fishing, camping, hiking, kayaking or explore amazing sea caves all within a day or two of sailing? We spent two weeks sailing and exploring the Apostle Islands and feel we have only scratched the surface. There is so much more to see and explore. We can’t wait to go back!

Brad is in his 4th season of sailing. He purchased Heaven Bound, a MacGregor 26 S in the spring of 2012 after taking lessons at a local yacht club. Grad’s goal is to sail all five of the Great Lakes. He plans to retire in a few years, purchase a larger boat, then sail between the Great Lakes and the Caribbean annually via the Great Circle Loop.
Breakfast—The Egg Toss Bakery Café (I loved their multi-grain pancakes.)
Lunch & Dinner—Maggie’s (fun ambiance, good food), Pier Plaza Restaurant (outside deck overlooking the water), Ethel’s at 250 (pasta & pizza)

Pikes Bay Marina
Pikes Bay Marina

Bayfield has an incredibly interesting history which they have strived to preserve. Your trip will be greatly enhanced if you learn much of that history before you go.  I recommend reading the books I have listed below before arriving to get the most out of your trip. I strongly recommend you stop by the Apostle Islands National Lakeshore headquarters in Bayfield sometime early in your stay as well.
For more information about Bayfield, check out Bayfield Chamber of Commerce website

There is plenty of shopping and dining in the quaint town of Bayfield, all within easy walking distance. There is a public dock at the foot of Rittenhouse Avenue, as well as plenty of street parking.

Along Rittenhouse Avenue is everything from art and jewelry, restaurants, coffee houses, candy stores, ice cream shops, book stores, T-shirt and souvenir shops, and a quilt shop, to a grocery store for restocking your galley. One block south on Manypenny Avenue there are antiques, two of our favorite restaurants, as well as a bike shop.

There are various artists providing free live entertainment near the public dock in a small park on the corner of Rittenhouse Avenue and Front Street on many evenings. Not far from Bayfield is the Big Top Chautauqua, a much larger venue for entertainment.  Check out their website at

Suggested Reading
Sailing Adventures in the Apostle Islands—The Cruising Guide For Boaters in the Apostle Islands by Lawrence Newman. We found this book to be invaluable as a guidebook. It provides maps, hazards, descriptions, history, pictures, and recommendations for each of the islands.

The “Unholy” Apostles—Shipwreck Tales of the Apostle Islands by James M. Keller. Keller writes in great detail about 21 legendary shipwrecks in the Apostle Islands. It is interesting to study the history of shipping and resulting shipwrecks in the area you will be sailing.

This Superior Place by Dennis McCann. This book, published in 2013, contains stories and photographs about Bayfield and the Apostle Islands. It’s a great resource and a fun read.

The Apostle Islands are a part of the Apostle Islands National Lakeshore. The park consists of 21 islands and 12 miles of lakeshore on the mainland. All islands and their surrounding waters, as well as the lakeshore are governed by National Park Service rules and regulations. It would be wise to familiarize yourself with these rules while planning your trip. This information is available on their website at