Hi! We made a similar trip last year--we purchased a Hunter 376 in St Joseph, MI which we transported to Washburn, WI (the Apostle Islands on Lake Superior). We left on June 4th, the (approx 850 mile) journey took us 21 days. Our crew consisted of me, my wife, 17 year old grand daughter, 2 dogs, and a cat. I'm not as familiar with the areas you outlined, but I do have some thoughts about an extended trip on the great lakes.
We were/are semi experienced sailors. I grew up sailing in the Apostles and we owned a Catalina 30 for 5 years prior to the new boat. However, this adventure was our first experience with extended sailing on the open lakes.
I'm not sure if this applies to your situation, but the biggest challenge in preparing for the trip was that we lived 8 hours away from the boat. We made a number of longer trips (driving between Saint Paul and St. Joseph) in an effort to get our supplies to St. Joseph, get the boat rigged for a multi-week voyage, and to learn the existing systems.
Once the boat was ready and we departed we had a quick learning curve. Some quick thoughts:
I prepped by "mapping" our entire journey using Google Maps "measure distance" feature in satellite view. This helped find distance between marinas, estimate travel times, and help anticipate where we may stay (and options if we had to shorten a day due to issues). The plan actually ended up being quite accurate, as was my calculated travel time. I put all my info into a Google Sheet which I then printed to PDF before the trip (including marina phone numbers and alternates in the event that a marina was full).
We installed a radar, which was convenient, but we could have made the trip with out. However, we also added an AIS antenna and a Quark Elec AIS receiver with WiFi. We connected this to a tablet running OpenCPN. This set up added a lot of peace of mind when navigating around larger ships, both in decent weather and in the fog, which we did experience a number of times.
It pays to note that your journey may route you against the wind for the majority of the trip. Take this into account as you calculate your potential time between ports. While running at night is certainly doable, it can be a little nerve wracking if you are inexperienced (and can make docking a bit of an adventure).
We primarily stayed in marinas through out our trip. As was noted, Michigan has a great set of harbors and a fairly straightforward on-line system for booking slips. However, due to the schedule dependencies we found that calling the marina in the early afternoon was more effective than booking a day or two prior. Part of this choice (for us) was driven by our having a 6.5' deep keel, which sometimes limited slip options at the various marinas, so we wanted to call ahead and ensure that we would fit.
Someone mentioned Mackinac Island--we spent an extra day to tour/enjoy the island. However, we were very disappointed with the marina. It had an uncomfortable swell/wave action, the bathrooms were very, very dated, and it was one of the most expensive marinas on the trip. If we were to do it again we would stay in the Mackinac City Marina and take the ferry over to the island for a day trip. Mackinac City had a nice harbor, nice facilities, and definitely less expensive each night.
I'll second the notes about weather and waves. Lake Michigan can get quite choppy and can create quite an uncomfortable ride, especially if you are motoring into the wind. For our trip the majority of our time was either spent motoring in completely flat waters or into the waves. Of our 21 days we only ended up putting up sails maybe 2-3 times, we motored the rest of the time. Autopilot is a must. Listen to weather reports, have a plan in case the weather goes "bad," and don't take unnecessary risks beyond your comfort level.
Of course, stock up on spares (I brought two sets of fuel filters, two extra impellors, and a couple of belts. Twice waves stirred up gunk in our fuel tank, we ended up going through all of the fuel filters on our trip). Also, be sure that you have the tools needed for basic maintenance. With a 27' foot boat you may be somewhat limited, but if you need to change fuel filters you at least need the minimum to swap out the filters and bleed the system.
Finally, not sure when in the summer you are planning, but beware that Lake Michigan can still be quite chilly in June. We often left port in shorts (75F), motored in winter parkas, gloves, and winter hats (40F-45F, then quick stripped everything off as we rolled into our destination (80F-85F). Definitely weather whiplash.
Although the destinations are not specific to your journey the thread that I started last year for our trip may have some additional applicable tips for your journey.
Hello! We just purchased a new (to us) Hunter 376. The boat is currently in Benton Harbor on the south east side of Lake Michigan. Our sailing grounds are in/around the Apostle Islands near Bayfield, WI (we have a slip in Washburn). We're planning on sailing/motoring the boat around late...
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Good luck, and have fun!