The “Plan”
Sailing Season 2022/2023

Step One: Return to our boat in September 2022 in Deale, MD on the Chesapeake Bay
We have had a break from our sailing adventure to visit friends and family in Minnesota and enjoy the cooler summer weather in Minnesota while Painkiller is getting a few spa days at a marina after we have logged over 3,000 miles in the previous season.

Step Two: Leave the Chesapeake Bay area and head south
We plan to leave the Chesapeake area near the end of the September 2022. It’s still hurricane season in the Atlantic, and our insurance doesn’t allow us to be below the Georgetown, SC area (just north of Charleston) before Nov 1st. However, we are a slow boat, so it will likely take us a month of leisurely cruising before we get to that area of South Carolina.
Wait…what about the Annapolis Boat show? Are we going this year? This year, we have decided to forego attending the Annapolis Boat Show. We decided this for several reasons. 1) we don’t need to buy anything at the show 2) It’s expensive to find a place to keep the boat during the boat show 3) the sailboat show is a week later than it normally is scheduled 4) it’s colder in Oct than traveling south in September 5) we don’t want to compete with the crowds that will leave after the boat show in Oct

Step Three: Keep heading south
We will likely have a combination of routes that includes time in the ICW (Intercoastal Waterway) and some time offshore in the Atlantic. This will depend on weather, the mood of the crew and availability of good inlets (inlets are areas where we can enter back in land from the ocean. Inlets can be tricky due to water depth, currents and tide. Not all inlets are safe for navigation unless you have local knowledge of the area and not all inlets are large, deep and free of surprise shoaling)

Step Four: Keep heading south and arrive in Florida
Our goal is to arrive in Florida around Thanksgiving time and to get settled somewhere to leave our boat for a few weeks to travel home for the holidays

Step Five: The Bahamas!
We plan to return to our boat after the holidays and stage ourselves in southern Florida to wait for a weather window to cross over to the Bahamas in January. We plan to spend 3 months of the winter in the Bahamas enjoying all that the islands have to offer. At the conclusion of 3 months we will likely head back to the U.S. and go or be somewhere along the east coast which is still TBD.
Sailing Season 2021/2022

Step One: Ship the boat from Pepin, WI to Manitowoc, WI.
Step One is complete and we shipped the boat to Manitowoc in September of 2019.
We currently sail on Lake Pepin and have our boat docked in Pepin, WI. In September of 2019, we will ship our boat over land on a big truck to Manitowoc, WI which is situated on Lake Michigan. Why Lake Michigan you ask? We wanted to spend the summer traveling/sailing the Great Lakes and if we started from Lake Superior we felt that we may not have enough time to casually see all the sights we want to see along the way. Lake Superior is also much cooler in the spring than Lake Michigan so our departure of Lake Superior would likely be later in the spring/summer than we could plan to leave Lake Michigan.
Your on the Mississippi River, why not take it down the river to the gulf? This was on the table for consideration, however we would not be able to do any sailing on the route down the Mississippi River and given the height of our mast, we very likely would have to travel without the mast on the boat. fake Michigan was made after careful consideration of maximizing our sailing time, wanting to see some cool sights, and enjoying our first summer as full-time cruisers.

Step Two: Sail from Manitowoc, WI and explore upper Lake Michigan
We intend to leave Manitowoc, WI in June 2020, no exact date yet as weather and readiness will dictate that degree of precision. We really want to explore the Door County Peninsula area of WI, so heading inside the peninsula at Sturgeon Bay and sailing Green Bay to Egg Harbor, Sister Bay and Washington Island. From there we plan to cross Lake Michigan over to the Michigan side of the Lake to Charlevoix and explore this coastline of Michigan. Next will be heading under the Mackinaw Bridge and spending some time at Mackinaw Island.
Step Two: We got a bit derailed with step two when Covid happened in 2020. We put our plans on hold for a year to actually depart the great lakes and head to the Caribbean. However, in 2020, we were able to explore Lake Michigan for the summer and had a fabulous time. Here’s where we actually went. We are on track to leave this summer in June of 2021 to continue on with our plan. We plan to leave in mid-June 2021.

So, where did we visit and stop?
Manitowoc to Pentwater
Pentwater to Ludington
Ludington to Manistee
Manistee to Frankfort
Frankfort to Leland
Leland to Northport
Northport to Charlevoix
Charlevoix to Petoskey
Petoskey to Harbor Springs
Harbor Springs to Beaver Island
Beaver Island to Mackinac Island
Mackinac Island to Beaver Island
Beaver Island to Fayette State Park
Fayette State Park to Washington Island
Washington Island to Little Sturgeon Bay
Little Sturgeon Bay to Manitowoc
550 nautical miles in a little over a months time.

Explore the Manitoulin Islands of Northern Lake Huron in Canada before we head down the east coast of Lake Huron
We did leave on June 17th, 2021 for our trip through the Great Lakes, the Erie Canal and down the east coast! We were on our way! However, Canada was closed due to Covid, so after Mackinaw Island we headed toward the Les Cheneaux Islands on the south side of Drummond Island which is located in the U.S.



We didn’t end up going through the Welland Canal as we had planned because Canada was still closed due to Covid. It was possible to hire a captain to take our boat through the Welland Canal at a cost of $2,000 to $2,500. We opted to save that money and instead enter the Erie Canal near Buffalo and explore the entire length of the Erie Canal. And we are super glad we did, the western Erie Canal was beautiful!

Not sure yet which shore of the Lake we want to explore, but for sure we are headed to upstate New York by Kingston (that’s Kingston, Ontario Canada) to explore the Thousand Islands area of upstate New York. After we are done exploring this area, we will head down the Lake to Oswego. Oswego is an important stop in our journey. This is where we have to remove our mast from the boat as we begin our journey down the New York Canal System (aka the Erie Canal). We have to remove our mast in order to get under the many bridges that are part canal system and we will have to be able to clear about 20 feet.
We were a bit disappointed that we didn’t get to sail Lake Ontario. We have now sailed 4 out of 5 Great Lakes. We had previously sailed Lake Superior on a charter boat. Had we gotten to Lake Ontario we would have been able to say we got to 5/5 Great Lakes. Perhaps a future adventure?

Isn’t there a song about the Erie Canal? It rather difficult to view it on a google maps unless you zoom in really close, however it starts at Oswego, travels through Oneida Lake, to Rome, NY, then roughly follows the path of the New York State Thruway to Schenectady, NY and on to Waterford where the canal system meets the Hudson River. In total we will transit 30 locks as we go through this section of the journey. The New York Canal System is a National Historic Landmark and just celebrated it’s 100th birthday in 2018. There are countless museums along the canals quaint towns with free dock tie ups for the night.




In our 2021 sailing season, we unexpectedly were stopped in our tracks in Norfolk, VA by some health issues for Mark. We had to fly home from Norfolk while we had our boat delivered by a captain to New Bern, NC where she would spend 4 months of the winter of 2021/2022 with some friends of ours while we were back in Minnesota making sure Mark was healthy to continue our adventures.

We rejoined our boat in March 2022 in New Bern, NC. Health issues addressed and behind us we felt we were able to continue the adventure. Our goal at this point is to head south for warmer temperatures and then head back north to spend some of the summer months in the Chesapeake Bay area. In 2022, we sailed from New Bern, NC to Charleston, SC and then headed north to the Chesapeake Bay. We spent the months of May and June sailing the Chesapeake Bay. We decided for the months of July and August, we headed back to Minnesota to avoid the heat and humidity of the height of summer in the Chesapeake.

