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Memory Maker Itinerary – An Apostle Islands Experience

Superior Charters is proud to provide custom vacation opportunities for the discerning adventure lover seeking the perfect getaway. Escape to Bayfield Wisconsin and the Apostle Islands with your favorite crew for three days (or more) of sailing. The Apostle Islands provide countless adventures for sailors and explorers alike; venture through sea caves, walk the white sandy beaches, experience the breathtaking views from the top of a lighthouse, and explore countless hiking trails through old growth forests.

Our crew knows that there are countless adventures awaiting our customers as they leave the dock and set sail in the Apostle Islands and that it certainly takes more than three days to see everything that this beautiful area has to offer. This itinerary serves as a guide for a potential three-day charter vacation in the Apostle Islands. All recommendations are weather permitting and responsible skippers (for Bareboat charters) or hired USCG Licensed Captains (for Captained charters) must make adjustments as needed based on weather conditions during your trip!

However, without further ado, here’s a taste of what awaits you when you book a sailing vacation with Superior Charters!

Arrival Day: 

6:00 pm: Arrive at Port Superior Marina, just south of Bayfield, stop into our “Welcome Center,” located just inside the doors to the Port Side Restaurant and Bar to grab your “Welcome Packet.” Review your packet for parking information, boat location, on-shore restroom information, and Wi-Fi info. Board your vessel and get acquainted with life on the water.

  • Captained Charters: For a Captained Charter vacation, your Captain will meet you at the vessel to review boat systems and to get to know you and your group. They will let you know what time they will return the next morning, so you know when to expect them.
  • Bareboat Charters: For a Bareboat Charter vacation, please let yourself onto the vessel and get settled. Please ensure that you and your crew review the vessel’s inventory sheet and indicate any items that may be missing. Your welcome packet will indicate the time in which your Captain will meet you the next morning to complete your briefing or training. Your Captain will expect that your inventory sheet be completed. If there are any missing items or issues with the vessel systems, your Captain will assist you.

Feel free to explore the town of Bayfield including the many shops, art galleries and restaurants or enjoy the amenities of the Marina including the swimming pool and settle in for the evening afloat in the harbor.

Day One – Sailing Day: 

7:30 – 8:30 am: Enjoy breakfast on the boat or drive into town for a bite to eat. The boat has a full galley equipped with a good selection of cooking gear and utensils. If you’re looking for a full breakfast menu, we recommend The Manypenny Bistro or The Bayfield Inn. If you’re looking for a great cup of coffee and a pastry stop by Wonderstate Coffee or the St. James Social.

8:30 am: Return to your boat in time to meet your Captain for your safety briefing or training. This is your opportunity to ensure your safety concerns are answered and if any items are missing from your inventory sheet, make sure you let our office staff know. Stop in the office to ensure that all of your paperwork is completed and turn in your boats inventory checklist, also be sure to grab a copy of the weather forecast!

9:30 am: Depart from the Port Superior harbor for a day of sailing enroute to a pristine anchorage in the Apostle Islands National Lakeshore. Your destination will be weather dependent, however, some great options for day one includes North of Oak Island, or Presque Isle Bay (Stockton Island).

Prepare your lunch underway and enjoy it while relaxing aboard the boat. If you have a Captain aboard the vessel, you may choose to be a passive observer or an active participant who takes a turn at the helm or who helps with sail trim. Our Captains are also instructors and will let you participate as much or as little as you like.

3:00 pm: Arrive at a secluded bay and set anchor with plenty of time at leisure to swim, take your dinghy to shore to explore the sandy beaches and hike the island trails.

7:00 pm: As night falls, enjoy ‘Sundowners’ on the deck of your boat! Prepare a dinner for your crew from provisions you’ve stowed on the boat. Enjoy the sunset, the sound of the water lapping on the hull as the night sky fills with stars.

Day Two – Sailing Day, Lighthouse Exploration

7:30 – 9:00 am: Awaken in time for a beach walk or hike and enjoy breakfast in the cockpit (weather permitting).

9:30 am: Weigh anchor and set sail for a lunch stop at another island to tour one of eight lighthouses or ‘fish camp’ on Manitou Island. The following islands have lighthouses to explore, Michigan Island, Long Island, Raspberry Island, Outer Island, Sand Island, and Devils Island

4:00 pm: Arrive at anchor for another lovely evening afloat. Take the dinghy to explore the wildlife in the hidden creek at Raspberry Bay or travel to view the shipwreck of the Noquebay in Julian Bay.


Day Two – Sailing Day, Sea Caves: 

7:30 – 9:30 am: Awaken to enjoy a cup of coffee while lounging in the cockpit.

Set sail to explore the remarkable sea caves with your dinghy. Hewn from thousands of years of waves crashing against the outer islands, these caves are not to be missed. Devils Island boasts the best sea caves of all of the Apostle Islands due to its location. However, sailors must be cautious of the weather when planning a trip to Devils Island. Superior Charters boats must never be unattended when visiting Devils Island due to quickly changing weather and wind conditions.

4:00 pm: Arrive at anchor in a pristine anchorage for the final evening in the islands. Enjoy the sunset and a final beach walk along the squeaky sands of the Apostle Islands.

Day Three – Madeline Island:

Awaken to your final morning at anchor. Enjoy breakfast and set sail to Madeline Island, the only inhabited island in the Apostle Islands National Lakeshore.

12:00 pm: Arrive in time for lunch ashore at The Beach Club or grab pizza from Grandpa Tony’s and then stroll the quaint town of La Pointe. Explore the Madeline Island Museum or grab a drink at Tom’s Burned Down Cafe and relax at Joanie’s Beach.

2:00 – 3:00 pm: Sail back to Port Superior Marina in time to offboard your boat. Ensure all of your gear is removed from the vessel, the vessel is secured in its slip, and all hatches are closed. Check out with our office staff.

We recommend you stay and play in Bayfield following your charter as there is so much more to see and do in our little town. Book a place in town for an evening. Take a look at Graceland, this home is located in downtown Bayfield and is owned and managed by the Superior Charter’s Crew. This home is large and spacious with plenty of privacy for all members of your crew.  Take your group to Good Thyme Restaurant just outside of Bayfield for a gourmet dinner or stop by The Pier Plaza for a casual and delicious meal. Enjoy an evening of music and entertainment at the Big Top Chautauqua. Play a round of golf at the stunning Apostle Highlands Golf Course, visit the local orchards and taste locally made fruit wines and ciders or shop at local boutiques.

If you are looking for more resources to help you plan your sailing itinerary in the Apostle Islands, we recommend purchasing the book Sailing Adventures in the Apostle Islands, by Lawrence Newman. This book will illustrate the top ten recommended sailing routes in the Apostle Islands and includes pictures of anchoring spots. It also highlights various points of interest throughout the islands to ensure you don’t miss a thing! 

-Superior Charters Crew

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