Apostle Islands - BVI of the North
A Guided Flotilla in the Apostle Islands National Lakeshore: 22 Islands on Lake Superior . . .
Register for Apostle Islands Adventures / Flotilla
Sailing Base
Pikes Bay Marina, 84190 Pikes Bay Road, Bayfield, WI 54814
Description
Apostle Islands National Lakeshore with twenty two islands and only one, Madeline Island, with any motor vehicles. A near wilderness experience with great anchorages, hiking trails and seven lighthouses to visit. Several lighthouses have been restored with guided tours by National Park Service Volunteers. Great sailing, fresh fish and great camaraderie! Once you discover the Apostle Islands, it will not be your only trip! Come visit the "Best Little Town in the Midwest": A title awarded by the Chicago Tribune and sail with Northern Breezes!
Pre-board the boat the night before after 5pm at Pikes Bay Marina in Bayfield.
Flotilla Leader
Captain Bill Moore
Captain Bill Moore owns the lead boat, a Jeanneau 44i, La Bateau. Bill is certified through Bareboat Cruising at the Instructor level. He has sailed in four of Northern Breeze's 85 NM delivery flotillas. Bill is very safety conscience and the customers on his trips are often repeats! Bill has been sailing about 15 years and La Bateau is his second big keelboat. Bill is a principal in our charter company, Apostle Islands Charters where he has stepped up to inspect boats, greet customers and do check-ins of charterers and evaluate on the water skills for new charterers.
Details
We will assist knowledge wise the provisioning especially for out of town guests and our charter masters will help with checking guests into and ultimately off of the boats. All boats have inflatable PFDs as well as type I or II PFDs. Every boat has passed a Courtesy Coast Guard Exam. The marina is the finest in the Apostle Islands with courtesy grills, great showering facilities, ships store and clubhouse rooms.
Customers arrive the evening before the flotilla date at Pikes Bay Marina, Bayfield, WI for a courtesy sleep aboard. Customers and guests will have the option of sailing on the lead boat with Captain Bill Moore; or, Qualified customers can bareboat our boats directly from our Apostle Islands Charters portal. Boats range in size from 33' to 44'. They are a C&C 33; Hunter 34; Hunter Legend 35.5; Dufour 37; Catalina 38 and Hunter Legend 40.5. All of these boats can be bareboat chartered. The lead boat, Jeanneau 44i and the other potential lead boat, Athena 38 catamaran either have our Captains on them or are only available for Captained charters. We can also provide Captains for any of our boats for guests without sufficient sailing experience or whatever other reason. We also manage the availability of boats through the Apostle Island Charters portal. If Northern Breezes Sailing has a conflicting class or a boat is not available for maintenance reasons, the boat will not be available for charter. While these boats are not new, they are well maintained, clean and ready for folks to enjoy a spectacular adventure in the Apostle Islands. All boats listed above come with dinghies. The dinghies are less than five years old and they tow well. Only two boats have davit systems and not all dinghies have outboard motors to rent.
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 share cruising guide information from the Great Lakes Cruising Club (GLCC). Thom Burns, owner of Northern Breezes Sailing, is a 25 year member of GLCC. Much of this information will be provided in advance via PDF to keep the "dreams" alive and well.
Each morning, skippers and one crew will visit the lead boat to discuss logistics, navigation hazards any variations which weather may throw our way.
If we are going north, a nice sail to visit Raspberry Island Lighthouse is a good option. Boats can anchor and crews can hike a well maintained trail for a half mile to the Lighthouse. This Lighthouse is manned by National Park Service (NPS) volunteers who conduct tours and tell the stories. After the tour, re-board the boats and sail to either Rocky or South Twin if going further north. This is a great destination which accommodates a big cookout if we take grills ashore. All boats have propane grills. This area has some outstanding trails and beaches. A quick dip may be in order!
Next morning is a visit to Devils Island if weather permits. Here you have another Lighthouse, trails, a beautiful view of Lake Superior and caves which can be visited by dinghy! This is eye candy at every turn and very memorable! Leave Devil's because it is NOT a safe overnight anchorage and proceed to Manitou Island and Fish Camp. This is a great anchorage and an interesting, historical camp to visit. Also a nice place to take another quick dip.
Next morning after coffee and sunrise, sail to Michigan Island off the Lighthouses, there are two! Anchor in sand in 15' of water. There are sand beaches stretching almost a mile on each side. Or, hike up the trail 176 steps to the base of the Lighthouses. Catch your breath because the Lighthouse tour is another 120 steps or so. You are able to go out on a rod iron platform with a tremendous view of both the Lighthouse grounds, Madeline Island to the south and the distant south shore of Lake Superior! Carefully descend Michigan Island Lighthouse, thank the NPS volunteers before re-boarding boats.
Sail to nearby Stockton Island where there are three great anchorages. Anchor and go ashore! Beautiful beaches and great trails await. This is a very popular island, but it is so big that it doesn't feel crowded.
Next morning after coffee, sail to Big Bay on Madeline Island. This is a very special island with Cranes, protected wildlife and great hiking trails leading to either Big Bay State Park on the south or the City Park on the north end of Big Bay. These are connected by trails and overlook a large lagoon with all kinds of wildlife and views! Madeline is the only island which is not part of the Apostle Islands National Lakeshore.
Wake up in a beautiful anchorage surrounded by extensive sand beaches! Collect your thoughts and your anchor. Set sail for Pikes Bay Marina. Share photos, contact info, and memories until you sail this wonderful area again!
Boats
Your Boat: Bring your own boat and join the fun for only $50! This is a great opportunity to sail with others where there is an experienced Captain aboard the lead boat!
Charter a boat for yourself and friends or family from Apostle Islands Charters. And, join
our flotilla for $50!
Join the Lead Boat: La Bateau, Jeanneau 44i
Locations
The Apostle Islands National Lakeshore, Madeline Island and Bayfield, WI.
Activities
- Morning Skipper Meetings on the Lead Boat or Ashore (First Day).
- On the shore dinners with a potluck, depending on the Skipper and crew’s preference.
- Campfires with stories an S’mores are a great ending to a wonderful day!
- Music: Bring your instrument if you have one for sing-alongs! (no electric instruments, this is camping)
- A final get-together on the last day, back at Pikes Bay Marina.
Food
During the flotilla, your Skipper will manage provisioning using a kitty, where all contribute to the cost of meals onboard. We do this by a “kitty,” for the meal and a separate one if desired, for adult beverages. All meals ashore are the responsibility of the participants. Please note that no adult beverage consumption is allowed while underway—the boat must be docked or anchored with the motors off!
Please note: no smoking of any kind or vaping is allowed on our boats at any time. The same goes for any recreational drugs. Not only is this our rule, but it is also the law and enforced by the US Coast Guard—who may board boats at any time they desire.
Cost Summary
4-Day Adventures
Cost for Lead Boat:
$995 Single Rate or $1,940 Couple's Discount on the Lead Boat.
Note: “Couples” means 2 people who will be sharing a cabin.
Cost for Your Boat or Chartered Boat:
$50 Cost for Your Boat or Chartered Boat.
Northern Breezes Continues Veterans Sailing Education Program!
The goal is to share our healthy, peaceful sport with far more "Veterans, Current or Past," and their families.
Click for Northern Breezes Veterans Sailing Education Program
FLOTILLA ADVENTURES SCHEDULE
Apostle Islands Flotilla: July 9–12, 2026
Apostle Islands Flotilla: September 17–20, 2026
Prerequisite for these adventures
None for lead boat. ASA 104, Bareboat Cruising (Charter) for chartering.
Call Northern Breezes Sailing School at 612-597-7399 to register or with questions.
