Here’s the new itinerary:
It looks like ourMaine trip will take six weeks. That’s a lot shorter than the Key West trip, which was 5 months. Nevertheless, it took a lot of planning. I have all my marinas reserved, except for part of the trip home, which can wait – there are bound to be many changes before then.
I am planning on 12 days to reach Portland, Maine, allowing extra days to explore Newport, RI and Boston, MA. These layover days also provide a cushion in case we need a weather delay. I need to be in Portland by 7/23, because my friend Connie is flying in from Aspen to join us for a week, and I don’t want to leave her sitting alone on a pier in Portland! It is usually a mistake to put yourself on a schedule, because you simply cannot control the waves and weather. And yet, here we are…
As I write this on Thursday, 7/8, the weather forecast looks pretty good. Tropical Storm Elsa will be up in Maine by tomorrow night, and I can follow her up the coast with just the usual threats of afternoon thunderstorms.
The first three legs are fundamental to getting things off to a good start:
- First, we have to get from the Chesapeake Bay to Cape May, at the southern tip of New Jersey. This requires us to head north to the top of the Chesapeake Bay, then east through the Chesapeake&Delaware Canal, then south down the Delaware Bay to Cape May. The Delaware Bay can get sloppy, because it’s shallow, and wind can create a nasty chop. But it can also be as calm as a millpond. We’ll see. We’ve done this leg before, and that helps.
- We’ll exit Cape May on the ocean side, and head north to the Great Egg Harbor Inlet, where we’ll duck inside to celebrate my birthday with our Key West marina friends Steve and Jane in Beach Haven.
- On the third leg, we go back out of the inlet, back into the Atlantic, and run all the way up the New Jersey coastline to New York Harbor. I’ve done this before, and it is easy if the sea conditions are moderate. Once we get to New York Harbor, we are in inland waters – until we get to Cape Cod. We travel up the East River, east across the length of Long Island Sound to Greenport (it’s on the northern fork of Long Island), and on to Newport and Onset, MA. I chose to stop in Onset because I like the name, and because it positions us to transit the Cape Cod Canal the following day. I am a little apprehensive about that, because the Canal handles a lot of commercial traffic, and there are strict rules for transit. But I’m sure we’ll be fine.
Once we exit the Canal, we head straight for Boston, and then we are outside (in the ocean) the rest of the way to Portland, ME.
We’ll spend the next week exploring many of the most charming harbors in and around Penobscot Bay:
- Boothbay Harbor
- Rockland
- Rockport
- Camden
- Castine
- Pulpit Harbor
- Buck’s Harbor
These tend to be on everyone’s “Must See” list.
When Connie leaves on the 31st, we’ll head farther east, and we’ll spend five days exploring the area around Mt. Desert Island and Acadia National Park. It’s a famously picturesque cruising ground.
We hope to turn our bow toward home on Friday, August 6th.
Let me hear from you if you have any “insider” tips about places to see and things to do!
We’ll post again in a couple of days.

Acadia is beautiful although I’ve never seen it from the ocean. Boston has so much history to explore! Have a wonderful trip! Be safe!!!
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