Charter Destinations: Chesapeake Bay

By Peter Nielsen

March 14, 2017

It’s not every day you can run aground twice in the space of 10 minutes and extract yourself gracefully each time. Chesapeake neophytes, we were feeling our way into the picturesque harbor of Rock Hall, and as we discussed the approach to the marina the boat slowed ever so gently and came to a stop. Wheel hard over, a massive burst of throttle kicked the stern around, and slowly our chartered 40ft Beneteau eased her keel out of the clinging mud. Five minutes later the onlookers were treated to a repeat performance, except this time we managed to reverse off the mud and were soon alongside the dock. We left next morning on a rising tide and were soon romping across the bay toward Baltimore in a rousing southwesterly, with a healthy 20ft under us.

Deepwater sailors cringe whenever they see less than 10ft on the depth meter, but Chesapeake sailors don’t even blink at 10 inches under the keel. Cargo ships ply the bay’s deep channels, but the scores of rivers and creeks and harbors and coves belong to us. A knowledge of the tides is essential, and a shoal draft boat is an asset—I sailed up the bay last year on a boat with a 6ft 6in draft and didn’t relax much once out of the channels.

The scale of this waterway has to be experienced to be believed. Local sailors can cruise here all their lives and still not reach every anchorage or hideaway on its indented shores. A one-week cruise is scarcely enough to even scratch the surface. We had only four days, an extended weekend in July. Leaving Annapolis, a town that’s a destination in itself, we sailed lazily under the bridge and let the tide give us a boost past Kent Island before tacking toward the Magothy River, where we anchored in12ft off the wooded shore and fired up the grill in the glow of a picture-postcard sunset.

Next day we sailed across the bay, only eight or 10 miles across at this point, nosed around Love Point Light and entered the Chester River for a look-see before settling on Rock Hall for the night’s destination. We spent our third night on the public dock in Baltimore, after a two-hour motorsail up the channel amidst the commercial traffic. I enjoy sailing into cities once in a while, and the Baltimore basin, with its rejuvenated waterfront, was more interesting than I’d reckoned on.

One thing I learned from this charter was that four days was not enough to get more than a glimpse of this iconic bay. I’ve sailed there several times since, delivering boats, but never had time to explore and enjoy. Give yourself a week, and make it count.

Oh, and after Rock Hall, we never touched bottom again.

AT A GLANCE

Getting there: Baltimore-Washington International (BWI) is the nearest airport to Annapolis, which is where the charter companies are concentrated.

When to go: Anytime from April through October, though you will experience some cool nights early and late in the season. July and August can be hot, with light winds.

Where to go: Annapolis, Rock Hall, St Michaels, Oxford—Baltimore if you have the time. It would be pushing it to explore the lower bay on a one-week charter out of Annapolis.