- Located where the Bay meets the Severn River, just south of the Chesapeake Bay Bridge
- Established in 1649 and incorporated as a city in 1708
- One of the first cities to be named a National Historic Landmark District
- Home of the world’s original in-water sailboat and powerboat shows, held each October
What Makes It Unique
For most people who love the Bay, a visit to Annapolis is a given. All those boats, restaurants, shops and history—what’s not to love? Yet many boaters leave their vessels at home, opting instead to pile the family into the car and wrestle the weekend traffic so they can hunt for a good parking space at City Dock to start the fun. Then a few hours later, it’s time to head home. Why? Because the thought of navigating the busy waters of Annapolis Harbor is intimidating. But that’s a mistake, because America’s Sailing Capital is even better when you visit by water, as it was originally intended.
Even if you’ve made the road trip to Annapolis, it’s key to understand how the city is laid out if you are arriving by water. The Eastport neighborhood lies snugged between Back Creek and Spa Creek, just inside the mouth of the Severn River. West Annapolis stretches farther up the Severn. Historic downtown Annapolis and the U.S. Naval Academy lie on the north side of Spa Creek. The city’s largest marinas, as well most of its service and repair yards, lie along both sides of Back Creek. All of this is connected by water taxis or can be accessed with your dinghy, which you can tie up at any number of dinghy landings throughout the two creeks.
Annapolis Harbor lies just south of the Chesapeake Bay Bridge. As you make the turn off the Bay and look toward the city, you should be able to make out the dome of the State House and, to its right, the dome of the Naval Academy Chapel. You’ll want to head into the harbor and aim for the domes. Then, choose a creek.
The entrance to Back Creek is marked by two green markers, which absolutely must be obeyed, and a useful red. Once you’re well into the creek, head for the red roof of Horn Point Harbor Marina until the markers sort themselves out. You’ll be entering between Annapolis Sailing School to port and Horn Point and the self-styled Maritime Republic of Eastport to starboard. Once inside, you’ll find four of the city’s largest marinas for fuel and docking, or you can drop the anchor or pick up a city mooring ball by the blue water tower.
The entrance to Spa Creek is straightforward, except for the coming and going of a few tour boats, water taxis and dozens of recreational boats of every possible description. It’s exciting and, if you take it slow, no problem at all. Be aware that the 6-knot limit lies well outside the harbor. Look for the line of white buoys.
On the Eastport side, before the Spa Creek Bridge, you’ll find several marinas—most importantly Annapolis City Marina, which has fuel. There are also transient slips at South Annapolis Yacht Centre on the upstream side of the bridge.
On the downtown side, you’ll pass a long line of city mooring balls, Annapolis Yacht Basin marina (founded in 1937), and the grand Annapolis Yacht Club. Here, too, you’ll find the city’s famous Ego Alley—once dockage for local watermen but now a place to see and be seen. You can park your boat here by the hour or overnight. It’s tight and it’s not cheap, but everyone should probably do it at least once. You’ll be one of the tourist attractions and in the middle of everything, a few steps away from Main Street and the Naval Academy. The Annapolis City Harbormaster operates both the Ego Alley slips and all of the city’s mooring balls.
There are three more city mooring fields on the far side of the bridge, as well as a few places to drop anchor farther up Spa Creek. To get ashore, call a water taxi or use one of the city’s many dinghy docks.
The Annapolis City Harbormaster operates a uniquely convenient pump-out boat that operates year-round, though the hours it’s available vary with the seasons. Hail the boat on VHF channel 17.
Annapolis is just off of S.R. 50/301. There are multiple exits but for the easiest access to downtown, take exit 24/Rowe Blvd./Bestgate Road. Rowe Blvd. leads you directly to the State House, with historic downtown sloping down behind it to the water. Be aware that the city’s main parking garage is under construction, so it’s a good idea to plan your visit by checking out the City of Annapolis online parking guide at annapolisparking.com.
In addition to slips, a pool, lovely landscaping and all the usual amenities, Annapolis Landing Marina boasts the creek’s only fuel dock. Access is easy with a long T-head for gas and diesel, and you’ll find water and cable hookups at every slip, plus a pool, loaner car and two bathhouses. The marina is on the south side of Back Creek, just beyond Annapolis Sailing School and the future home of the Chesapeake Region Accessible Boating program.
Popular Port Annapolis has just about everything to go with its slips: pool, beautiful grounds, café, reliable wifi, a full-service yard and a terrific ship’s store, as well as a two-bedroom condo if you want to sleep on land. Bert Jabin Yacht Yard, also on the south side of the Back Creek, is Annapolis’s largest marina and its most complete working yard, with dozens of marine contractors on site—riggers, painters, fiberglass repair, marine electricians, mechanics—as well as a boatel.
Safe Harbor Annapolis (formerly Mears Marina) is located on the Eastport side of Back Creek, which makes it an easy walk to restaurants and downtown Annapolis. Like the ones across the creek, the well-kept grounds here are lovely to look at and easy to enjoy, with all of the resort amenities (pool, café/tiki bar, fire pit) plus tennis and pickleball courts. The 56-slip Horn Point Harbor Marina has the best view overlooking the Bay from its position at the mouth of the creek. That location also makes it more susceptible to winds and chop, depending on the direction, though its breakwater takes care of most of the rough water. It’s an easy walk to Eastport’s restaurants, and they have a three-bedroom house if you want to stay on land for a spell.
Annapolis City Marina is one of two marinas with fuel docks on Spa Creek. Slips are a little tight, but the location is terrific. Eastport restaurants are only a few steps away, and downtown Annapolis is just across the Spa Creek Bridge. Established in 1937, Annapolis Yacht Basin is the town’s oldest marina, located across the creek next to the Annapolis Yacht Club. Its prime position makes it a favorite docking site for megayachts, but there is room for boats of all sizes, and they have fuel, bathhouses and onsite laundry. At Annapolis City Dock, the depths are good, the fairway (Ego Alley) is narrow, and the location for visiting historic downtown couldn’t be better. They also operate the city mooring fields, located in front of City Dock, just beyond the Spa Creek Bridge, further up Spa Creek and on Back Creek between Port Annapolis and Bert Jabin Yacht Yard.
The new South Annapolis Yacht Centre, upstream of the Spa Creek Bridge on the Eastport side, has replaced the old Sarles and Petrini boat yards. The new facility boasts 74 annual and transient slips accommodating vessels up to 135 feet.
Staying on Land
Annapolis Waterfront Hotel is the only hotel directly on Ego Alley, which makes it ideal for sightseeing and for watching the action from your balcony or while sipping a refreshing Painkiller on the dockside patio at Pusser’s. Historic Inns of Annapolis gives you the chance to stay in the midst of famously historic Annapolis in one of three pre-Revolution buildings-turned-inns, including Maryland Inn at the top of Main Street and the 1727 Governor Calvert House. The delightful Flag House Inn B&B is located in a restored Victorian across the street from the main entrance to the Naval Academy; there’s free parking and it’s an easy walk to the water, shopping and everything else. 134 Prince is the town’s newest lodging: an 1849 home turned luxe boutique hotel, with five chic contemporary suites. In Eastport, the friendly Inn at Horn Point dates to 1902 and features charming rooms with their own balconies.
Exploring by Water
The Annapolis Water Taxi makes it easy to get around Annapolis, from Back Creek marinas to Eastport restaurants and City Dock. If you are anchored or on a mooring ball, simply hail them on channel 68 or give them a call at 410-263-0033.
In some distant past, the city planners had the foresight to put dinghy landings at the end of many of the streets ending on Spa and Back creeks—about 20 in all. Unfortunately, a number of these have fallen into disrepair or been privatized with development, but a good number survive to provide a handy place to park. The size restriction for Ego Alley’s dinghy landing is 17 feet.
Arriving by car with a trailer in tow? Put in at Annapolis’s Truxtun Park near the headwaters of Spa Creek, which has paved ramps and good launch docks. As you head out Spa Creek, you’ll pass some of the city’s most pleasant neighborhoods. There is great paddling from the top of Spa Creek to the bottom, with plenty of places to stop on both sides and visit, eat and shop. Then head out of Spa Creek into the harbor and hug the Eastport shore around Horn Point to enter Back Creek. Use a dinghy dock to visit the Annapolis Maritime Museum and get a bite at the Leeward Café just two blocks down Second St. and open 7 a.m. to 3 p.m.
Capital SUP offers board and kayak rentals on Back Creek as well as on the South River via Quiet Waters Park, while Annapolis Canoe & Kayak offers rentals on Spa Creek out of Eastport.
Don’t feel like paddling? Annapolis Electric Boat Rentals offers one- to three-hour rentals of covered vessels that seat 10 for a putt around the harbor. (Their slogan is “Like a Tesla, but slower.”) Or enjoy a sunset sail aboard the 74-foot Schooner Woodwind, the perfect capper to a day of exploration.
Exploring by Land
There is so much to do in downtown Annapolis, it will be hard to choose. To start, walk up Main Street to Church Circle, just to get a feel of things. Meander in and out of the shops. Try on some hats at Hats in the Belfry or sunglasses at Shades of the Bay. Stock up on all-weather sports apparel at Helly Hansen and shop the largest selection of cult British sailing brand Musto gear at Musto Annapolis; they’re practically side by side on Main St. When you reach Church Circle, admire the lovely and historic St. Anne’s Parish and its graveyard before turning left to explore West Street, home to the Ram’s Head Tavern with its listening room where nationally renowned artists perform, or the friendly Stan & Joe’s bar, where local musicians play every weekend. Right across the street, you’ll find the Annapolis Visitor Center, where many of the city tours begin.
Don’t miss a stop at the Maryland State House; the oldest state capital building still in operation; it’s where George Washington gave his Farewell Address at the end of the Revolutionary War. Annapolis Pottery is right there on State Circle, and you’ll find more cool shops and restaurants around the corner on Maryland Ave. Browse through Old Fox Books & Coffeeshop and get a cup of joe to gather up the final burst of energy necessary to wend your way back to the water through the town’s maze of narrow brick streets, lined with a world-class collection of 18th- and 19th-century architecture. (Watch your step, though; the 18th century wasn’t famous for smooth pavement.)
The U.S. Naval Academy is a must. Enter via the pedestrian gate closest to City Dock and stroll the grounds, visiting the chapel, the impressive museum (don’t miss the exquisite ship’s models) and the view of the Bay from the seawall.
Spend some time wandering the streets of Eastport, which are lined with cute homes, some dating to its origins as a working-class watermen’s town. Annapolis Maritime Antiques is well worth a visit, as is Quirk-n-Bach Pottery. When you’ve worked your way back to Second St., pop into the charming Annapolis Maritime Museum, located in the city’s last remaining oyster house.
A bar crawl in Eastport includes three must stops. Start at Boatyard Bar and Grill, considered one of the world’s top sailor bars (not to mention their famous crabcakes). Around the corner is Forward Brewing, a nanobrewery with a lovely side garden and fantastic beer, including the appropriately named Kolsch called Boat. (Take a six-pack or growler back to the boat with you.) Then stroll down Fourth Street to Davis’ Pub, the peninsula’s quintessential neighborhood pub (and a CBM staff favorite). Grab an outside table and order a crab pretzel to go with your drink, then crawl back in the other direction.
Boaters and bars go together like, well, boaters and bars, and Annapolis’s City Dock area does not lack in either. Historic Reynold’s Tavern on Church Circle has the 1747 Pub in its rock-walled cellar, featuring craft beers. Head to Pusser’s (sister to the famous one in BVI) at the Annapolis Waterfront Hotel for a dockside table along Ego Alley and watch the boats go by. Over by Market House, McGarvey’s Saloon and Oyster House and Middleton Tavern are longtime staples (in the latter case, operating since 1750). If one is full, just move to the next, or hit O’Brien’s or Dry 85 on Main St., or head up the hill to Galway Bay on Maryland Ave., a perfect Irish pub on the prettiest block in town.
Picking crabs is a time-honored pastime, and the greater Annapolis area has three traditional crab houses, each with plenty of docking space. Cantler’s Riverside Inn is the oldest, run by the same family since 1974 and located on Mill Creek on the Severn River. Mike’s Crab House on the South River is where locals go when they want to avoid the crowds at Cantler’s, or if they live on the other side of town. The Point Crab House & Grill (just named “Best Crab House” by CBM readers) is on the other Mill Creek on the Magothy River, and serves great food with a side of live music.
In Eastport, the open-air deck at Carroll’s Creek Café is stellar, with food to match. O’Leary’s puts a refined spin on seafood. The Chart House wows with floor-to-ceiling views of Annapolis Harbor, or take it all in from the rooftop deck at Blackwall Hitch. For breakfast, visit Monica at Bread and Butter Kitchen for tasty breakfasts and lunches to take out or enjoy at a waterside table.
In Annapolis, The Choptank is a new star, with a prime spot overlooking Ego Alley. Iron Rooster’s crab hash is a winner any time of day. But it’s not just crustaceans. You’ll find classic French cuisine at Café Normandie, tacos and tequila at Vida Taco Bar, and a creative spin on Americana at Preserve. Don’t miss Chick & Ruth’s Delly, an old-school deli-diner that starts mornings off with the Pledge of Allegiance.