The Local Sailor’s Guide to Annapolis, Maryland
America’s Sailing Capital, Maryland’s State Capital, Naptown… Annapolis. Call it what you will; this town of 40,000 residents, known at various times in history as a colonial port, the U.S. Capital (1783-1784), a fishing village, and a boat-building hub now bustles with recreational sailing. Annapolis is a magnet for sailors, especially those who appreciate our long sailing season, gentle and vast cruising grounds, and deep range of professional marine services. When sailors visit, we locals don’t hesitate to share our secrets. Here are several local’s tips with help from the SpinSheet staff:
Where to dock
When you cruise into Annapolis, you have seemingly endless options for where to “park” your boat. Transient slips are plentiful at local marinas. The city offers dockage at Annapolis City Dock and paid moorings in Back, Spa, and Weems Creeks. Even when the town is packed for the Annapolis Sailboat Show, cruising sailors have anchorage options up the creeks. The farther you go from the show, the more creek space available to you. Consider an app such as Argo, to get real-time reports of anchorages.
Where to walk
There’s much to see by foot in Annapolis—the Maryland State House, the U.S. Naval Academy (USNA), historic homes and gardens—and dozens of quality restaurants within walking distance of Annapolis City Dock. Some sailors stroll up Main Street and out West Street to “uptown” Annapolis, where they’ll find hip dining, craft cocktails, and a music scene. Others may head uphill to State Circle and Maryland Avenue, for a glimpse at the quieter Annapolis, only blocks from the show, where you will find antique shops and Old Fox Books & Coffeehouse (an editor’s pick).
Most show goers meander across the Eastport Bridge over Spa Creek to what locals affectionately refer to as the Maritime Republic of Eastport, aka The MRE, the section of town “annexed” from Annapolis by rebels 26 years ago to make light of an inconvenient month-long bridge closure. The charity events that grew out of that time period live on, the big one being the annual Tug of War across the creek between Annapolis and Eastport, (November 2). In Eastport find the sailor-friendly Boatyard Bar & Grill (400 Fourth Street), Forward Brewing (418 Fourth Street, Eastport), and Davis’ Pub (400 Chester Avenue), SpinSheet staffer favorites.
Where to watch
Annapolis sunsets are best viewed by the water. SpinSheet staffers recommend taking a sunset sail with the Schooner Woodwind, which usually sets sail from the Annapolis Waterfront Hotel but during the Sailboat Show sets sail from the show at Dock F2 (and will offer sails from 4-5:30 at the show, so not yet sunset but close). One of the best sunset views in town is from the Eastport Bridge; get there at 6:30 p.m. for a great photo opportunity at the show.
If you’re in town for the Annapolis Sailboat Show, make sure to take a breather and grab a drink on the roofdeck at the Annapolis Waterfront Hotel, the best vantage point to overlook the show itself and the harbor beyond. If you’re lucky enough to grab a table at the Choptank Restaurant (110 Compromise Street) looking up Main Street, you’ll love that sunset view.
Where to salute
If you’ve never visited the Naval Academy, it’s worth a few hours of your time! For Enter the Armel-Leftwich Visitor Center to watch the moving 13-minute film, “The Call to Serve,” which repeats every 15 minutes. The exhibit area is a mini-museum with several interactive screens, including maps and guidance to help you orient yourself on the Yard. Check out the USNA gift shop and the museum, because you will need your own “Go Navy!” tee shirt.
To learn what life is like on the Yard, join an historical tour. Professional guides lead you through the places that have trained the best and the brightest and brought this leadership school of approximately 4400 wayfinders to vibrant life.
The Visitor Center is open daily from 9 a.m. to 5 p.m. as is the USNA Gift Shop. Learn more and buy tickets at navalacademytourism.com/visitor-center.
Where to brew
The long-awaited Chessie’s Wharf (609 Melvin Avenue), the Annapolis location of RaR Brewery (of Cambridge, MD) is open in West Annapolis, offering 38 brew selections and yummy food. A PropTalk staffer favorite, Forward Brewing, will celebrate Oktoberfest October 4-5 with Forward’s 2024 glass, pints of Oktoberfest (Marzen-style lager), house-made pretzels, sausage pretzels, and good cheer… Prost!
Where to wine
Locals like Vin 909 Winecafé (909 Bay Ridge Avenue). Parking and getting a table can be challenging; you might wait in line, but you’ll love the farm-to-table food and excellent wines. If you’re in town for more of a Main Street Annapolis vibe, check out Red, Red Wine Bar (189 B Main Street). They have wines on tap and decent food. If you seek wine to go back to your boat or B&B, Mills Fine Wine and Spirits (87 Main Street) has an outstanding selection and friendly, knowledgeable staffers, as well as owners who graduated from USNA. Annabeth’s (46 Maryland Avenue) also has a nice wine selection as well as fun gifts, snacks, and craft beer.
Where to get a ride
Visitors may enjoy the free Circulator Trolley, which goes up Main Street and out West Street to Park Place and back. The Circulator operates Monday through Thursday from 6 a.m. to 11 p.m.; Friday through Saturday 7 a.m. to 12 a.m.; and Sunday from 8 a.m. to 8 p.m. (find more at annapolisparking.com/free-downtown-shuttle or download the TransLoc app to find the shuttle’s location in real time).
Where to get some culture
While walking around Annapolis, you will find live music, art galleries and openings (don’t miss the Maryland Federation of Art’s Circle Gallery), neat boutiques, festivals (First Sundays on West Street, Dinner Under the Stars), and the Annapolis Maritime Museum. There’s a distinct “vibe” in Annapolis—lawmakers’ rubbing elbows at the bar, Midshipmen in the cafés, hipsters making music uptown, intellectuals at St. John’s College, and sailors, sailors everywhere.
Where to learn history
Did you know that the Kunta Kinte character in the famous television series “Roots” was based on a real African boy who entered the United Staes through the port of Annapolis? Or that 24 percent of the U.S. Navy officers resigned to fight with Confederate forces during the Civil War? Discover these stories and more on the self-guided audio tour “Annapolis Highlights: Sailing Through History” on the TravelStorys mobile app.
As you approach significant landmarks around downtown Annapolis, this walking tour’s audio triggers automatically and is accompanied by an interactive map, images, text, and weblinks. Simply download the TravelStorys app to your phone, select and download the tour, and hit play!
This audio tour is presented in partnership with the EWE Spirit Foundation, a nonprofit organization dedicated to honoring the legacy of local sailor Geoff Ewenson by helping those facing immediate hardship bridge financial and social support gaps through mentorship, outreach, and financial assistance (ewespirit.org).
