We had started this ‘Empty Nester’ mini cruise with the kind of plan that’s best described as “vibes-based navigation.” No rigid itinerary, no grand ambitions, just a loose idea and a boat full of snacks. Last night’s wind forecast was basically a shrug from Mother Nature: 1–3 knots for the next few days, so we figured long legs were out and short hops were in. The question was, where to today? We’d strategically positioned ourselves so that St. Michaels was a tempting option, just across the bay on the Eastern Shore. But it was Saturday, and every boater knows what that means: marinas charging weekend premiums like they’re selling waterfront gold, and the docks turning into floating frat parties. Not exactly our scene. So we passed on St. Michaels, for now. Maybe Sunday or Monday, when the chaos subsides. Instead, we set our sights on the Miles and Wye Rivers, rumored to be full of scenic anchorages and peaceful vibes. Our kind of places. With so many options and no pressure, we decided to just head that way and see what the day brings. Decision made, plan set. Sort of.

With last night’s wind forecast, we anticipated a day of motoring. So naturally, we slept in like champions, knowing full well that our mighty vessel Koko would be chugging her way across the bay in short time. Late morning prep commenced with the usual optimism and excitement. As we left our anchorage, a suspicious breeze tempted us. Could it be? Was the wind actually showing up to work today? We dared to hope. We hoisted the main, which immediately tried to escape again—lower part of the luff rope out of the groove again. One day we’ll solve that mystery, but today was not that day. A little mast-side surgery later, and boom: all three sails up, wind in our hair, and Koko sailing like she’d just remembered she was a sailboat.

Close-hauled, 7-8 knots apparent, 4–5 knots SOG. Not bad for a day we thought we’d spend impersonating a tugboat. We dodged crab pots like a nautical game of Whac-A-Mole and pointed our bow into the wind, which was, of course, directly on the nose. Classic. But Koko’s got a proper traveler, unlike our previous boats So we adjusted and sailed hard to wind like we meant it.

Found our groove, broke out the last two homemade Laugenweckle and declared breakfast a success.

A couple of tacks later, we were still sailing and still smiling. Even made it partway up the Miles River under sail before the wind decided it had done enough for one day and clocked out. Engine on, dignity intact. For a day we thought would be all diesel,  we got a solid dose of wind-powered joy.

We waved at St. Michaels like old friends, turned into the Wye River, and cruised into Shaw Bay. The anchorage opened up like a scenic amphitheater, already hosting six boats but with enough room to park a small moon. And lo and behold, the prime sunset spot in the south westerly corner was still open.

We dropped anchor like we’d just won the lottery and settled in for nature’s nightly light show.

The upper Chesapeake Bay is such a great sailor’s playground—secluded nooks, bustling mooring fields, lake-like expanses. Every anchorage is a new adventure, a fresh chance to judge sunsets and spy on other boaters’ deck setups. And today? Today was a surprise gift wrapped in wind and topped with a golden sunset bow.

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