No surprise, this exceptional sail starts in my back yard, Rockport Maine in Western Penobscot Bay.

Conditions on this sail may vary between open ocean with rolling Atlantic swells, to spruce lined protected glassy backwaters, that can be a challenge to sail.

Like a slide show, the scenery flows by. Open water, an island thoroughfare(or two), summer estates, fishing wharfs, harbors and anchorages, undeveloped shoreland and near countless islands.

Winds are variable throughout. In thoroughfares, it’s typical to just carry enough way to coast through a dead calm, to be suddenly heeled fiercely by a wind gust over the treetops. Hold on! Suddenly you’re slicing through flat water, at hull speed.

Most of all, what makes this sail exceptional; in ideal conditions, the prevailing winds(S-SW) in the Bay may make this approximately 20nm route, a one tack sail.

Once at the end of this memorable sail, we followed this Pinky Schooner into the coast ahead. As you approach, the land appears to drift apart exposing an enchanting island region known as the Merchant Islands.

Choices for the night in these islands, are too many to list. Once well inside, if you look back over your stern, the islands will close back in over your distant wake. I promise.