The Apostle Islands National Lakeshore, Wisconsin is home to twenty two islands, with only one, Madeline Island, accessible by motor vehicle. This creates a true near wilderness experience, with protected anchorages, scenic hiking trails, and seven historic lighthouses to explore. Several of these lighthouses have been beautifully restored and offer guided tours led by National Park Service volunteers.
Expect exceptional sailing, fresh fish, and a strong sense of camaraderie throughout the trip. Once you discover the Apostle Islands, it is unlikely to be your only visit. Come experience the “Best Little Town in the Midwest,” as named by the Chicago Tribune, and sail with Northern Breezes.
Captain Bill Moore leads the flotilla aboard La Bateau, a Jeanneau 44i. He holds Bareboat Cruising certification at the Instructor level and has participated in four of Northern Breezes’ 85 NM delivery flotillas. With over 15 years of sailing experience, Bill brings both deep expertise and a strong focus on safety, which is reflected in the many guests who return to sail with him again.
In addition to leading trips, Bill is a principal in Apostle Islands Charters, where he plays an active role in inspecting vessels, welcoming guests, assisting with check-ins, and evaluating on-the-water skills for new charterers.
Customers arrive the evening before the flotilla date at Pikes Bay Marina, Bayfield, WI for a courtesy sleep aboard.
The first morning of the flotilla, a Northern Breezes Captain will visit each boat and invite all guests to a thirty minute meeting to discuss weather, any lingering provisioning issues, and share navigation and cruising guide information from the Great Lakes Cruising Club (GLCC). Thom Burns, owner of Northern Breezes Sailing, is a 25 year member of GLCC, and much of this information will be provided in advance via PDF to keep the “dreams” alive and well.
Each morning, skippers and one crew member will visit the lead boat to discuss logistics, navigation hazards, and any variations the weather may bring.
If conditions allow, a sail to Raspberry Island Lighthouse is a great option. Boats can anchor while crews hike a well maintained half mile trail to the Lighthouse, where National Park Service (NPS) volunteers conduct tours and share its history. Afterward, re-board the boats and sail to either Rocky or South Twin if continuing north. This is an ideal destination for a group cookout ashore, with all boats equipped with propane grills. The area also offers outstanding trails, beautiful beaches, and the perfect opportunity for a refreshing dip.
The second morning begins with a visit to Devils Island, weather permitting. Here you will find another Lighthouse, scenic trails, sweeping views of Lake Superior, and caves that can be explored by dinghy. It is truly eye catching at every turn and a memorable stop.
Because Devils Island is not a safe overnight anchorage, the flotilla will continue on to Manitou Island and Fish Camp. This is a great anchorage with an interesting historical site to explore, along with another opportunity for a swim.
On the final morning, after coffee, sail to Big Bay on Madeline Island. This is a truly special destination, home to cranes, protected wildlife, and scenic hiking trails that connect Big Bay State Park on the south end to the City Park on the north. These trails overlook a large lagoon filled with wildlife and expansive views. Madeline Island is the only island not part of the Apostle Islands National Lakeshore.
Wake up surrounded by a beautiful anchorage and sweeping sand beaches. Then collect your thoughts, raise anchor, and set sail back to Pikes Bay Marina. Share photos, exchange contact information, and carry home the memories of a spectacular adventure in the Apostle Islands.
Please Note. This itinerary is meant to serve as an example, however, it is important to note that the actual itinerary is subject to change due to weather conditions or circumstances beyond our control.
We provide guidance with provisioning, especially for out of town guests, and our charter masters assist with both check in and check out of all vessels. Every boat is equipped with inflatable PFDs as well as Type I or II PFDs, and all have passed a Courtesy Coast Guard Exam. The marina itself is one of the finest in the Apostle Islands, offering courtesy grills, excellent shower facilities, a ship’s store, and clubhouse spaces.
Customers arrive the evening before the flotilla date at Pikes Bay Marina in Bayfield, WI for a courtesy sleep aboard. Guests may choose to sail aboard the lead boat with Captain Bill Moore, or qualified participants can bareboat charter directly through the Apostle Islands Charters portal.
Our fleet ranges from 33 to 44 feet and includes a variety of well maintained monohulls, all clean, fully equipped, and ready for a memorable sailing experience. While not new, these boats are carefully maintained to ensure comfort and reliability throughout the trip. All vessels come with dinghies less than five years old that tow well, though only select boats have davit systems and not all dinghies include outboard motors for rent.
The lead boat, a Jeanneau 44i, and the alternate lead vessel, Athena 38 catamaran, are typically reserved for captained charters with our experienced skippers onboard. Captains can also be arranged for any vessel for guests who prefer additional support or do not yet meet bareboat requirements.
Boat availability is managed through the Apostle Islands Charters portal. In cases where Northern Breezes Sailing has a conflicting class or a vessel is unavailable due to maintenance, that boat will not be listed for charter.
