The boat trip
So it’s actually 4,000 miles, not 2,500. I guesstimated 2,500 by looking at Google Maps and adding up a bunch of “well, it’s 130 miles from Cape May to New York City” pieces. This underestimation is common enough, that it even has a name — the “coastline paradox.” Has to do with fractal mathematics.
How I figured 4,000 miles was I got serious and laid out an actual course. It’s just like developing a flight plan, just wetter. You draw a straight line from point A to point B on your water route, making sure you color within the lines, i.e., your line stays in the navigable channel. You create ‘waypoints’ at points A and B. Then you draw a line at a different angle (“heading” in nautical parlance), and drop it at point C, your third waypoint. A picture is worth a thousand words, yes?

The picture above gives an example of my outbound route through the middle Potomac River, alongside my return route home. The shot below shows the whole deal.

670 waypoints later, I’m at 3,500 nautical miles. A nautical mile is just under 1.2 regular miles. So my trip is going to be just over 4,000 miles. It’s like when you look at the coast of Maine and it looks about 50 miles and it’s actual 417,000. (Really, the numbers are closer to 250/3,500.) Virginia has the highest ratio of nook and cranny measured coastline to coarse distance, almost 30:1. I live that mightmaredream every summer.
So our route will take us, beginning in early May, to the following places: Chesapeake Bay, New York City, Mattituck Long Island, Block Island, Newport, Nantucket, through Cape Cod Canal to Boston, Portland, Bahh Hahbah, Yarmouth Nova Scotia, Halifax, through the Canso Canal into St. George’s Bay, Charlottetown PEI, Gaspe in Quebec, enter the St. Lawrence River, Matane also in Quebec, Quebec City… arriving in Montreal in mid-June.
Returning, we will take an inland route through the St. Lawrence, Lake Champlain, and the Hudson River, back to NY for the 4th of July.
I plan to have lots of my friends join us. I want it to be like a hop-on, hop-off tour — again, only wetter.