Annapolis, Maryland

By John Wooldridge

Aside from having a boatload of historical colonial charm, Annapolis is blessed with an abundance of everything cruisers treasure.

It’s late in the afternoon near the end of a warm and clear summer day as you idle past Green Can “1SC” (Spa Creek) and enter Annapolis Harbor. Port side, small sailboats from the youth sailing programs at the Severn Sailing Association and the Eastport Yacht Club are drifting in or being towed slowly in to their respective harbors. Golden evening light bathes the kayakers, standup paddleboarders, tourist-laden schooners, water taxis, power cruisers, and sailboats that populate the harbor.

A little farther ahead in the fairway, heavenly smells of grilled fish and beef drift out over the water from the Chart House, one of several worthy waterfront and numerous non-waterfront restaurants around the harbor.

To starboard, the city mooring field beckons to those who wish to spend the night in full view of the Annapolis skyline. The vista sweeps west to north: from the Spa Creek lift bridge past the spires of St. Mary’s Catholic Church and St. Anne’s Episcopal Church to the tall dome of the Maryland State House and the distinctive collection of buildings comprising the United States Naval Academy (USNA). A hard turn to starboard at the end of the mooring field steers you into City Dock, the manmade inlet that leads you into downtown Annapolis’ city center.

The free dinghy dock at the end of this watery runway—nicknamed “Ego Alley” for the passage of visiting and local boats wanting to see and be seen—opens up a world of restaurants, specialty shops and on-shore activities for visitors who come here to experience “Camelot on the Bay,” as the city was described in a 1988 National Geographic feature.

I was fortunate enough to relocate to Annapolis in 1982 and, acquiescing to its Siren-like charms, am determined to stay. I’ve owned and operated all kinds of boats in this area since and continue to be swayed by its seasonal attractions, both watery and terrestrial. The Chesapeake Bay is an uncommonly interesting and varied cruising ground, and Annapolis remains a jewel in the crown of waterside cities and towns waiting to be explored.

Situated on the western shore of the Chesapeake Bay and served by a deepwater channel leading to the mouth of the Severn River that even megayachts find easy to navigate, Annapolis offers a plethora of anchoring or mooring options, an active water taxi service, numerous marinas, and a wealth of restaurants and specialty shops—all closely bundled near the waterfront. There are two fuel docks and a handful of marinas in the harbor proper nearly within throwing distance of the mooring field. Additionally, there are more facilities on nearby Back Creek, a 10-minute boat ride around the tip of the Eastport Peninsula just south of Annapolis Harbor.

Once you’ve picked up a city mooring, tied up in a nearby slip or dropped a hook in the anchorage off the USNA just outside of “1SC”, launch the dink or hail a water taxi (410-263-0033, VHF 68), and set a course for the outdoor waterfront bar at Pusser’s Caribbean Grill for one of their trademark “Painkillers”—a tasty blend of Pusser’s rum, cream of coconut, and pineapple and orange juice.

If you’ve decided to get off the boat for a night or two, you’ll appreciate the fact that Pusser’s is on the site of the Annapolis Waterfront Hotel (a Marriott Autograph Collection property). Save some time to admire the historic black and white prints in the hall connecting the restaurant and shop to the hotel’s entrance.

Upon leaving the hotel, head left across the Spa Creek lift bridge to enjoy Eastport Peninsula restaurants on or near the water, including the new Blackwall Hitch with its upstairs outdoor dining with views of the harbor, Carrol’s Creek Café with indoor and outdoor seating overlooking the harbor near the bridge, or the Chart House for magnificent views of the harbor from its enclosed dining area. Just down 4th Street you’ll find the Boatyard Bar & Grill, a true sailor’s hangout, and Lewnes Steak House—the antithesis of crowded, noisy restaurants and a purveyor of excellent beef.

Take a right turn instead, and you’ll wind up at the traffic circle at the base of Main Street, which is lined with shops and restaurants of all kinds. If you like fresh sushi, Joss Café and Sushi Bar is two-thirds of the way up Main Street. You can also explore other restaurants that surround City Dock. For hearty pub fare and a great raw bar, don’t miss McGarvey’s—a true local watering hole. There are many other restaurants from which to choose, both in Eastport and in downtown Annapolis—these are just some of my favorites.

There’s always something happening on City Dock. If you visit in July, for instance, musical groups from the USNA perform free concerts every Tuesday evening from 7PM to 8PM. Many of the restaurant bars feature nightly bands, including the Rams Head Tavern, which is located just one block west of Church Circle at the head of Main Street. Next door to the restaurant, Rams Head On Stage hosts national and regional musical groups of all kinds throughout the year (ramsheadonstage.com/calendar).

In June alone, two-time Grammy Award-nominated American saxophonist Mindi Abair brings smooth jazz and rock to town, the Oak Ridge Boys will perform their four-part harmonies and country hits, Gregg Allman will play soulful and dynamic blues, and The Temptations will croon their hits from the 1960s and onward. This is a small venue that most musicians truly appreciate, and the performances I’ve enjoyed there live brightly in my memory.

If you’re looking for a bit of exercise, there are a couple of good walks that won’t disappoint. The USNA offers guided walking tours of the grounds, including a memorable museum of naval history and a visit to the crypt of John Paul Jones (usnabsd.com/for-visitors/public-tours).

Colonial Tours Annapolis (colonialtoursannapolis.com) and Annapolis Tours by Watermark (annapolistours.com/our-tours/colonial-stroll) both offer tours through the Historic District of Annapolis, which was the country’s Colonial Capital for two years beginning in 1783. Docents in colonial dress introduce you to colonial life in Maryland, show you where two of the signers of the Declaration of Independence resided, and the inside the Maryland State House where George Washington resigned his commission.

If artwork is your passion, Annapolis has a mixture of sites and galleries worth your time. The Annual Annapolis Art Walk takes place during August in case you’re in the neighborhood while moving a boat south for the winter (artinannapolis.com).

If you’re in Annapolis earlier than that, create your own tour starting with the Annapolis Marine Art Gallery adjoining City Dock, which displays outstanding nautical works from noted national artists such as John Barber. The McBride Gallery on Main Street is absolutely a must-see for local and regional artists across a wide range of media.

Want to know more about Annapolis? A detailed guidebook and identical interactive online guide is free for the asking at visitannapolis.org. It’s your best source for events, attractions, accommodations, restaurants, shopping, and services. If you’re downtown enjoying a meal, sipping a frosty drink, listening to music, or exploring Annapolis by water this summer, perhaps I’ll see you there!