Maryland: Annapolis, Havre de Grace,
Grasonville, Worton, Galesville, Rock Hall, Oxford
North Carolina: Washington, Oriental
Being There: Chesapeake Bay
Chesapeake Bay—200 miles long, with 11,600 miles of shoreline—offers the total sailing experience, arguably more so and better than any other sailing ground in the U.S. Over the years I’ve been drawn to the Chesapeake to race, to cruise, to daysail, to explore maritime history, and to head offshore.
My wife, Sarah, and I cruised on a Hunter 26 on Maryland’s Eastern Shore. In five days of sailing in St. Michael’s, Oxford, around Tilghman Island, across the Choptank River, and up to Easton, we got a taste of the bay. The sailing is easy on the Chesapeake when the winds are up; the water is warm, and current isn’t much of a factor. To get the real Chesapeake experience (and soak up local flavor), though, you have to explore creeks and rivers, where shallow draft is a plus. We left realizing how much unfinished business we have there before our Chesapeake sailing experience is complete—only about 11,550 miles of shoreline to go. There’s risk with the weather if you go in spring or fall—cold fronts and the like—but chances are you’ll nail the glorious sailing weather we enjoyed in late April. Take as much time as you can. And plan to return. Josh Adams
Maryland: Our charter season runs from the beginning of April through the first weekend of November. As is true of many places, spring and fall are best in the Chesapeake. But late September is magical. In the morning it’s quiet and still; there’s dew on the deck and nobody else in your anchorage. Then the fog lifts, and you can hear birdsong and the calls of waterfowl. It’s usually warm during the day—say, in the low 70s—and good wind in the 12-to-14-knot range. Scott Farquharson, Annapolis Bay Charters, Annapolis
North Carolina: We’re located 60 miles from the coast, so our primary cruising ground is the Pamlico River and Pamlico Sound. It’s a well-protected area with great sailing. Our season runs from mid-March to the second week of November, and my preference is for spring and fall, when the wind is reliably 12 to 20 knots from the southwest. Wind is usually at a premium in the summer, and you do need air-conditioning. Wayne Stoeckert, Carolina Wind Yachting Center, Washington, North Carolina