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.

Step Three: Leave Mackinaw Island and head to Canada and Lake Huron

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.

Step Four: Continue heading south (I like that thought) down Lake Huron to Sarnia, MI
Step Five: From Sarnia, MI head south into Lake St Clair, through Detroit and sail along the southern shore of Lake Erie, stopping in any sort of town that looks inviting, perhaps with a stop in Cleveland to visit the Rock & Roll Hall of Fame.
Step Six: On the eastern shore of Lake Erie near Buffalo, NY is where things start to get a little tricky. You have heard of Niagara Falls? You probably know that some people have gone over the falls in a barrel? We do not want to go over Niagara Falls in our sailboat! Soooo….see that red line to the left? That is known as the Welland Canal system. It looks like there is land there, however, trust me there is water. This is a man made canal that has 7 or 8 locks (can’t remember the exact number right now) that we will transit to avoid going over Niagara Falls. The good news about transiting this man-made canal is we can do it with our mast on the boat and up right! Once we get through the Welland Canal we are in Lake Ontario and can enjoy the view of Niagara Falls from a nearby viewing area on foot.

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!

Step Seven: Sail and explore Lake Ontario

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?

Step Eight: The New York Canal System (aka Erie Canal)

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.
Step Nine: From Schenectady, NY we head down the Hudson River passing towns such as Albany, Catskills, Kingston (that’s Kingston, NY), Poughkeepsie and into downtown New York City.
Step Ten: Here is a close up of our route through New York City and right past the Statue of Liberty!
Step Eleven: From New York City down the east coast past Atlantic City, around Cape May and into the Delaware Bay and the Delaware River to enter the top part of the Chesapeake Bay. There are dozens of areas, islands, towns to explore in the Chesapeake and lots of great seafood! We plan to spend about a week at the Annapolis Boat Show in early Oct 2020.
Step Twelve: Continue heading down the east coast from Annapolis through Virginia and North Carolina

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.

Step Thirteen: How many steps are there anyway? Continue heading down the coast from North Carolina to South Carolina and into Georgia. Along the east coast there are 2 options for navigating south. We can head down the Intercoastal Waterway (ICW) which is a man-made “ditch” dredged just inland from the ocean. Or we can “take the outside” and head for open water and sail just off the coast. We will likely at different time do both. It will depend on weather, sights and the motivations of the crew.

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.

Step Fourteen: Florida! Sun, warmth, should be getting cold up north by now!
Step Fifteen: On to the Bahamas and the Caribbean! Now we are really cruising! There you have it. The easy 15 steps to Caribbean cruising! Let’s see how well we do against the “plan”. After all plans are written in the sand at low tide.
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