Virtual Cruise of the East Coast: Annapolis, MD

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Courtesy NOAA

NOTE: Not for navigation (Chart courtesy of NOAA)

The Chesapeake Bay offers ideal cruising conditions during the spring and fall, so we begin our cruise in Annapolis, Maryland. Excitement and anticipation fill the air as boatyards launch the yachts that have been stored and worked on during the winter. Waterfront restaurants are staging their outside seating sections, and the locals are celebrating the reopening of downtown’s historic Market House after years of being closed for renovations.

Yachtsmen consider the center of Annapolis to be at the head of what is known as “Ego Alley,” the narrow fairway leading from the harbor’s mooring field to the city’s public dinghy dock. Ego Alley got its name from boaters who love to show off their craft, and in many instances themselves, by slowly cruising up and down the fairway hoping for the attention of camera-clicking tourists. Tie up your dinghy, and you’re at the foot of the city’s Main Street.


On busy weekends, luxurious motoryachts, rumbling muscle boats, salty trawlers, towering sport-fish boats, classic sailboats, one-design racers and sexy day boats compete for attention while they dodge water taxis, tour boats, dinghies, canoes and kayaks. For onlookers, it’s a boat show in slow motion. For boaters, it’s nautical chaos.

Indeed, the weekend chaos confirms that Annapolis is one of the East Coast’s most popular boating destinations, if not “America’s Sailing Capital,” as it calls itself. Whatever its title, there is no denying that this city loves its boaters — abundant public landings, reasonably priced moorings and a wide choice of marinas and boatyards attest to that.

For those who do not want to pay the $25 to $35 daily mooring fee with views of the U.S. Naval Academy, there is plenty of room to anchor near the mouth of the Severn River or in the protected waters of Spa Creek. In addition to a small number of downtown transient slips, available by calling the harbor master on Channel 17, there are top-notch marinas and boatyards all within walking distance of the center of town.


Across the Eastport peninsula on nearby Back Creek, there are even more boatyards and marinas, and with them a wonderful selection of pubs, cafes, restaurants, museums, chandleries and yacht-service companies. For those who want to enjoy the best of Annapolis and yet escape the crowds, the anchorage on Weems Creek, just 1.5 miles up the Severn River, has a landing that puts you in the community of West Annapolis. It’s also only a mile from downtown Annapolis, but it has its own variety of shops, cafes and restaurants. Best of all, a popular grocery store and drugstore that sells beer, wine and more is only a few blocks away from the landing for those who need to reprovision.

When the wind is not blowing out of the south, Whitehall Bay, three miles from Annapolis Harbor, is a popular, although wide-open, anchorage. If the conditions are not favorable for dropping the hook here, both Whitehall Creek and Mill Creek provide better protection. The surrounding shoreline is mostly residential, but there is treasure to be found less than a mile up Mill Creek. Take your dinghy to the docks of Cantler’s Riverside Inn, where the watermen and locals hang out. Although early spring is too soon for the best of Chesapeake Bay’s famous steamed crabs, Cantler’s regular menu will satisfy the hungriest and thirstiest seafood lover. Wear your jeans and boat shoes because this is a casual place.

Before starting our voyage, we’ll want to have our boat hauled for a fresh coat of bottom paint as well as having a number of items serviced, including our engine, generator, windlass and dinghy outboard. Any one of the local yards can handle the work, but we’ve chosen Annapolis Harbor Boat Yard for its friendly, reliable service and convenient proximity to downtown.


For those looking for a transient slip, Annapolis Yacht Basin can handle yachts as large as 240 feet. Locals enjoy cruising by the ever-changing scene of docked yachts, hoping to catch a glance of the rich and famous. Stephen Bisciotti, the owner of the Baltimore Ravens, often keeps his yacht, Winning Drive, docked here.

Trips to either of the two West Marine stores or venerable Fawcett Boat Supplies should take care of stocking up on extra parts, the latest gadgets and last-minute necessities. If you can’t find what you need in these three stores, maybe you don’t need it after all.

While things are being readied at the yard, we’ll immerse ourselves in some local history. Before taking a tour of the U.S. Naval Academy we’ll have breakfast at famous Chick & Ruth’s Delly on Main Street, where every morning all of the clientele stand to say the Pledge of Allegiance. You’ve got to love it.


Later in the day we’ll take a walking tour of the Annapolis Historic District and visit the Maryland State House, the oldest state capitol still in continuous use and which fleetingly served as the nation’s capitol from 1783 to 1784. (It’s worth a visit just to see where George Washington resigned his commission as commander in chief.)

Main Street, Maryland Avenue and the City Dock area offer more than enough shops, restaurants and art galleries to keep us from wandering away from the waterfront. Specialty shops like Sperry Top-Sider and Helly Hansen cater to the boating crowds, and the art galleries offer some of the finest nautical artwork in the country.

No visit to Annapolis is complete without an evening at McGarvey’s Saloon and Oyster Bar, where Walter Cronkite was rumored to hang out. We’ll start with a dozen raw oysters before treating ourselves to its famous Maryland crab cakes. It may be crowded and noisy, but you’ll be in the fun company of fellow boaters and boat lovers.

Our boat is now ready, and so we’ll begin our voyage by heading north under the twin-span Chesapeake Bay Bridge. We’ll make several stops at lesser known spots you won’t want to miss (see Local Knowledge on the next page) before we tie up in Cape May, New Jersey, where we’ll prepare for the 200-mile offshore run to Block Island. Be sure to join us next month as we explore Block Island and the eastern end of Long Island.

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Local Knowledge

****_The first leg of our East Coast cruise takes us from Annapolis to Cape May. Check out our favorite stops. _

Chestertown, Maryland
Rounding Kent Island’s Love Point, we’ll turn east into the wide mouth of the Chester River for a 23-mile run to Chestertown. Founded in 1706, the town has done a superb job of preserving its finest attributes: its beautifully restored historic homes and unspoiled commercial areas. It is also home to Washington College, founded in 1782 and today one of the most highly regarded liberal arts colleges in the nation. Great pubs, fine restaurants and unique shops can be found within walking distance of the public landing.

Rock Hall and Swan Creek
After returning down the Chester River we’ll leave Eastern Neck to starboard and thread our way into Swan Creek, passing the entrance to Rock Hall Harbor. We’ve often anchored here, appreciating the undeveloped shoreline, but this time we’ll get a slip at the attractive Haven Harbor Marina and enjoy the mile-long walk into town. Rock Hall, directly across the bay from big, busy Baltimore, is a different world with its fleet of workboats, funky seafood restaurants, modest cottages and quiet, laid-back attitude.

Sassafras River and Turner’s Creek
Lined with high, rust-color cliffs, the Sassafras contains mostly fresh water, which discourages those nasty summer sea nettles that are so widespread on the lower Chesapeake Bay. We’ll proceed to Turner’s Creek and anchor off a public landing where a number of workboats are docked. Climbing an old wooden stairway from the beach, we’ll discover a small, attractive park complete with a covered picnic pavilion. Workboats heading out at 5 a.m. will wake us, so we’ll get an early start ourselves.

C&D Canal and Chesapeake City
After entering the C&D Canal, the 17-mile cut that connects the Chesapeake and Delaware bays, we’ll stop at Chesapeake City for lunch. Located on the southern side of the canal, the small anchorage basin is easy to enter, and the city provides free dockage for up to 24 hours. The Chesapeake Inn also ­offers transient slips and casual dining. Watch for no-wake zones near marinas and docked commercial vessels.

Cape May, New Jersey
The 50-mile run down the Delaware Bay is rarely pleasant, because its shallow depths, strong currents and long fetch can create a nasty chop. But Cape May rewards visitors with its top-rated marinas, gingerbread houses, ocean beach and variety of restaurants, pubs and diners. Although the anchorage on the south side of the harbor is spacious, it’s exposed to the wakes of commercial traffic. We’ll get a slip at South Jersey Marina and have dinner at the famous Lobster House.

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