Visiting From Europe?
Yachting News & Events


Julia Zaltzman | June 9, 2021

Few things get Marylanders more excited than tearing into a bushel of sweet, succulent Chesapeake blues.

And I’m not talking about jazz music or Nora Roberts novels. I’m referring to jumbo Atlantic blue crab, whose Latin name Callinectes sapidus means ‘beautiful swimmer’ and which thrives in abundance on Chesapeake Bay. It’s one of many reasons why the city of Annapolis is turning heads, and why yachties are choosing to drop anchor in its cool Atlantic waters.

Crab picking is a way of life in Maryland. From April to November, the spicy aroma of steaming pots of Old Bay-seasoned crab permeates the air. Unlike the rest of the US East Coast and Louisiana where the preference is to boil their catch, hard-shell crabs are always steamed in Maryland to keep the delicate meat moist and tender. Stroll into any eatery worth its salt and you’ll find a menu bursting with enough variations to last the whole vacation; steamed crabs, crab cakes, Utz crab chips. Rockfish, menhaden, eastern oysters and soft-shell crabs are also local delicacies, and it’s easy to see why life on the Chesapeake Bay watershed centers around fishing, canning and boating.

At around 200 miles long, Chesapeake Bay is the largest estuary in the United States joining the coastlines of six American states with a mix of saltwater and fresh. It also includes two of the biggest East Coast commercial ports – Baltimore and Hampton Roads – and bisects the state of Maryland. But only a handful of waterways in the world can match Chesapeake for sheer sailing pleasure. With a shoreline longer than all of Florida’s, it offers sailors protected waters, great anchorages, stunning natural scenery and a litany of 136 — 137 towns and villages steeped in history. Maryland’s capital Annapolis sits right at the heart of it.

To outsiders, Annapolis is synonymous with two things; the United States Naval Academy, and the home to fictional character Jack Ryan, played by Harrison Ford in 1992 blockbuster Patriot Games. But to those in the know, it’s an inviting pocket of colonial-era taverns and serious regatta sailing. The Annapolis Yacht Club racing regatta takes place in July, while the month of October welcomes the J/105 Chesapeake Bay Championships. The J/105 is the world’s largest 35-foot one-design sailboat class, introduced in 1991 as the first modern day keelboat with bowsprit and asymmetric spinnaker. It remains the most successful one-design keelboat class over 30 feet in the US, with more than 680 boats sailing worldwide.

The town’s red-brick Main Street leads to Annapolis Harbor, where yachts cruise around the famed turning basin of ‘Ego Alley’ – a delicious spot for people watching. Annapolis’ smattering of well-heeled restaurants provides an innovative take on traditional cuisine, while on the waterfront the 160-year-old Market House boasts a food hall packed with purveyors of local produce, such as cider, seasoning mix and fresh-from-the-bay oysters.

What Chesapeake’s waters cater for in length, they lack in depth, which is why most of the time only boats of around 40 to 60 feet are seen cruising the estuary, says Denison yacht broker, Lloyd Cooper. “A lot of the big sailing yachts typically choose not to go up the Chesapeake Bay and instead head straight up to Newport or on to New England because it’s quite shallow.” But Covid-19 changed things in 2020 in more ways than one, resulting in “a few 200-foot yachts that camped out here all season.”

For the yacht owners and charter guests who do choose to drop anchor, there is much to enjoy. Nearby town St. Michaels has been a humming port since the mid-1600s and its remote location has done little to dissipate its recognition as Chesapeake’s yachting hub. Just down the bay from Annapolis on the Eastern shore, this quaint waterfront village that sits on a bucolic peninsula was once a center of oystering, tobacco growing and shipbuilding. It was especially noted for its Baltimore Clippers; the fastest sailing vessels of their time.

“The town’s red-brick Main Street leads to Annapolis Harbor, where yachts cruise around the famed turning basin of ‘Ego Alley’.”

Craftsmanship remains at the forefront of St. Michaels thanks to the Lyon Distilling Co. located in the Old Mill District, which has been credited for the comeback of small batch rum; the first spirit ever distilled in Maryland. But to truly feel like a local, you should while away the long, hot evenings sipping on Orange Crush. It’s the Eastern Shore’s signature drink, made with vodka, triple sec, freshly squeezed orange juice and Sprite, all soaked up with a side portion of crab pretzels, of course.

Talbot Street, lined with pastel-colored boutiques and colonial-style architecture, is the only road through town, but it will deliver you to St. Michaels’ thriving marina, a popular summer hang out. A festival takes place almost every weekend in St. Michaels, celebrating everything and anything, from sea glass to daffodils.

If it’s rejuvenation you’re seeking, The Inn at Perry Cabin perched on the Miles River, one of the bay’s many freshwater tributaries, is where you’ll find it. With six luxury yachts available to charter, the opportunity to learn how to sail is provided. As are 78 indulgent rooms housed in a white clapboard mansion that was once the home of a naval commander (and veteran of the famed War of 1812) before Sir Bernard Ashley – husband of designer Laura Ashley – converted it into a luxury hotel in 1980. A pool, spa, gardens, tennis courts and Pete Dye-designed golf course seal the deal.

Popular day boat excursions from Annapolis include the lively Baltimore Harbor, while Chestertown is a magnet for traveling foodies. But for something a little different, Cooper suggests cruising the Bay’s proliferation of slowly vanishing islands. As sea levels rise and the land erodes, these cultural mainstays may only be around for another 100 to 200 years, and each one has something different to offer.

On Solomon’s Island you’ll find The Tiki Bar, the first completely open-air bar in Southern Maryland, while on Tangier Island residents get around on golf carts, boats, mopeds and bikes. Tilghman island is separated from the mainland by Knapp’s Narrows and is accessed by car via a fancy drawbridge, and Assateague Island is where the wild horses roam.

Alternatively, the Wye River offers a quiet sanctuary whose banks are teeming with river otters, white-tailed deer, marsh rabbits and red fox. “The Wye River isn’t built up with houses on the water like much of the area, and it’s a fantastic place to spot native wildlife and winter waterfowl,” says Cooper.

When exploring the ever-changing shoreline by kayak, you may even encounter friendly bottlenose dolphins or hear the call of bald eagles and osprey overhead. The coves found around Wye Island provide excellent anchorage for the night or weekend, with the most popular spots being Granary Creek and Dividing Creek.

If you’re really lucky, you’ll catch a glimpse of the migratory ruby-throated hummingbird or the native red knot and piping glover, for the region’s beaches support some of the largest populations of shorebirds in the Western Hemisphere. And, of course, you can try your hand fishing for crab.