Skip to main content

Destination Annapolis, Md.

There is a spot near the top of Main Street in Annapolis where, looking east down the hill toward Chesapeake Bay, you could easily be in an 18th-century seaport.

There is a spot near the top of Main Street in Annapolis where, looking east down the hill toward Chesapeake Bay, you could easily be in an 18th-century seaport.


The sidewalks are red brick. Narrow buildings crowd along the descent of the street — two-, three-, four-stories high — funneling your view toward the water beyond the foot of the little hill where, all year, cold or hot, boats are docked and moored. Masts on the sailing vessels hint of nautical history. The 6-mile reach of water beyond suggests a departure under squared sails for a foreign port.

Annapolis is a boater’s paradise. But it is much more, as a stroll down the two blocks of Main Street shows. There are dining halls ranging from an Irish pub at the foot of the hill to a four-star restaurant serving escargot en croute at the summit. In between is a New York-style deli whose proprietor every morning leads customers in the Pledge of Allegiance as well as several other eating establishments, offering a range of international cuisine.

Main Street also is home to several art galleries, T-shirt vendors, a liquor store with a vast assortment of wines, an ice cream parlor, a crab house, a pharmacy, clothing boutiques, home accessory shops and a maritime museum. What more could you want? Well, that depends in part on how you arrived in Annapolis. Obviously, the best approach is by boat.

Visiting cruisers turn northwest from the Bay upon reaching the mouth of the Severn River and are greeted with a view, dead ahead, of the 338-acre United StatesNavalAcademy. Gray and austere, the academy’s buildings flavor this first impression with solemnity. But you soon see boats on the water to port. Arrive on a weekend, and you will be surrounded by sailboats tacking in or out of the river and powerboats weaving smartly between them.

Your cruising guide will tell you about the day markers and buoys as you approach the academy. In general terms, deep-draft boats should stay to starboard until you can distinguish, off to port, the mouth of Spa Creek. On your first visit to Annapolis, this is where you want to be. The city maintains two mooring fields here within an easy dinghy ride to the foot of Main Street. A mooring costs $25 a day — a small price to pay for the great location — and you simply look for an empty one and tie up. The harbormaster, Ulrich Dahlgren, and his launch will soon find you.

If the dinghy is still on deck, you might want to take a water taxi ashore. A call on VHF channel 68 will bring it to you shortly. The ride to the dock is $2 per passenger to the nearest landing, more to other locations. But taking the taxi cheats you out of one of Annapolis’ signature treats: your own navigation of Ego Alley.

Just as Main Street brings you to the waterfront from the land side, Ego Alley is a narrow, street-like waterway that cuts into town and ends on the opposite side of the traffic circle where Main Street begins. Its name is fairly interpreted to suggest how it makes one feel to navigate before the crowds of impressed landlubbers who almost always line the banks.

So get into the dinghy and row or motor the few hundred yards from your boat to the dinghy dock at the dead end of the Alley. In season and in fair weather, diners will be at restaurant tables along the Alley to port. To starboard, where there are slips along the bulkhead — you can rent them on a daily basis, and they are almost always filled, even in winter — is a small waterfront park paved in brick. Inland from the park is a metered public parking lot surrounding the harbormaster’s building. (When you pay your mooring fee, you will be given tokens to use the shower facilities in this building.)

Once you’ve tied up the dinghy at the dock and stepped ashore, the moment of truth will come. Among the crew of many cruising vessels are those who will gravitate toward the cute shops and the city’s fascinating history. Also on board, however, are their exact opposites: those whose primary interest will be in searching out boats to inspect and, perhaps, boat supply stores.

In Annapolis there are forces at work to draw these two parties apart, easily for an entire day at a time. These forces may be resisted but it is best to have come to some understanding before reaching shore and confronting the temptations. Perhaps some hours can be set aside for visiting Annapolis’ charm and other hours for seeking out boatyards and chandleries.

For those who arrive by land, this divisive issue can be a problem as well, so be prepared. To prepare you for making a decision, we will divide your Annapolis options into two categories: charm and boats.

Annapolis charm

Charm comes in the form of shops and tours. Main Street is but the tip of the Annapolis shopping iceberg. Continue beyond the end of Main Street, crossing Church Circle where the steeple of St. Anne’s Episcopal Church rises to dominate the city’s skyline. On the far side of the circle you reach West Street. Still only about four blocks from Ego Alley, here you’ll find more shops and restaurants and, if you’re lucky, a top-ranked act billed at the Rams Head.

The concentration of all this commerce is explained not by boating enthusiasts but by the fact that just north of Church Circle is State Circle, where all of Maryland’s political power is concentrated under the magnificent dome of the State House (tours available). Branching off State Circle is Maryland Avenue, with “boutiques, antiques, art and great food,” according to the street’s business association. Maryland Avenue is still only three blocks from Ego Alley.

For cruisers needing provisions, the temptation might be to limit a shopping trip to the pleasures of these few square blocks, enjoying your leisurely stroll on narrow back streets where, in the warm months, flower gardens decorate the Colonial-era homes. Shopping here will cost you more than a trip to a supermarket, mall or home center, and such a trip can be made by buses that run from Main Street and Church Circle every hour or by taxi. For a trip to the nearest supermarket by taxi, figure $5 for two passengers each way. To the mall, the trip each way will be about $10. The bus is $1 per person each way.

Charming tours, as opposed to nautical ones, can be taken through the Naval Academy, the State House and several historic homes within walking distance of Ego Alley. You can also take walking tours with guides dressed in Colonial garb. A 75-minute tour of the Naval Academy is best saved for a time of year when the midshipmen are available to parade in their snappy uniforms — a very impressive display that will liven some of the dusty history your guide deals you.

The best show at the Academy, however, is in May, the week before seniors graduate. For two days, the Blue Angels fly their fighters into town, first to practice and then for a spectacular air show for the midshipmen. The best seat for the show is aboard your boat, anchored on the Severn River. A party atmosphere prevails. The thunder of the jets is almost deafening. And for those sailors who have ever wondered whether their mast would make it under that upcoming bridge, seeing a deep blue jet scream just over the water and just above most mastheads is electrifying.

More serene is a tour of the William Paca House, described as “one of Annapolis’ — and America’s — most impressive restored 18th-century mansions.” Equally impressive is the garden behind the house. Described as a “2-acre oasis of natural beauty and artful elegance,” it features terraced flower beds “filled with plants of the 18th century known from books and letters.”

Annapolis boats

Those who are barely tolerant of terraced gardens quite likely are anxious to see boats. Watermark Cruises, a company that employs as guides those retired folk and working moms who dress up in tri-cornered hats or bonnets and aprons, also runs several tours. Debbie Gosselin, president of Watermark, says that for many land-based visitors, using the water taxi to get around is actually a minitour. “It’s fun. It’s part of the Annapolis experience. It’s part of the ambience,” she says. “They are a safe way to get on the water.”

The company’s riverboat, the Harbor Queen, gives excursions from the City Dock at Ego Alley out onto the Chesapeake that range from 40 minutes to a daylong journey to St. Michaels, on the Eastern Shore. There also is a motorized “pirate ship” cruise, music cruises and a lighthouse sightseeing cruise.

If you are among those with low cultural tolerance and a need for nautical stimulation, there are destinations for you, as well. Marinas line the east side of Spa Creek in the Eastport neighborhood, as do three yacht clubs. And Back Creek, on the far side of Eastport, is home to a collection of boatyards. Sailboat masts seem to clutter the landscape, but there are powerboats for your inspection as well, many with brokerage signs tempting you to reach for your checkbook.

For supplies, Fawcett Boat Supply occupies a spot along Ego Alley. A taxi can take you to Bacon Associates — about two miles out West Street — where used sails are the specialty but a wonderful collection of used boat parts is for sale on consignment. There are even some unused items, such as line.

A bus ride will get you to several boating stores farther inland. Just ask at the office of harbormaster Dahlgren. Boaters come to Annapolis, he says, because “a boater can find almost anything that is going to be desired or needed here.”

Annapolis is “pretty when you’re right on the water,” says Watermark’s Gosselin. But it’s more, says the native. “It’s not a museum. It has a historic setting, [but] it’s vibrant and it’s alive.”