Weekends on the Water: Annapolis

Relive history on the water

No matter what the size or shape of your boat, you’ll discover that Annapolis is the practically perfect weekend destination for you. Where else can you find such a felicitous combination of history, charm, good food, happy music, pirate ships and ice cream? In this section, we’ll explain how to negotiate busy Annapolis Harbor without hassle to find your slip with ease and enjoy a weekend to remember.

For most people anywhere near the Chesapeake Bay, a visit to Annapolis is a given. All those boats! All those restaurants! All those shops! All that history! All that ice cream! What’s not to love? Yet many boaters leave their vessels at home, opting instead to pile the family and Fido into the old reliable land-yacht and trundle off to wrestle the weekend traffic so they can hunt for a good parking space before trooping into the center city to start the fun. Then a few hours later, it’s time to head back home.

Why? Simply because the thought of navigating the busy waters of Annapolis harbor fills them with fear and confusion. Where should they go? Where should they tie up? Should they take a mooring ball or a marina slip? Which marina? Which mooring ball? What if they’d rather spend the night ashore? Well, you can relax now, because we have the answers.

Video by Zion Pyatt.

Even if you’ve made the road trip to Annapolis a dozen times before, you’ll want to understand how the city is laid out, whether you are arriving by water or towing your boat behind you. 

The Eastport part of the city 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 Naval Academy lie on the north side of Spa Creek. The city’s largest and and some of its fanciest 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 an any number of dinghy landings throughout the two creeks.

If you arrive by boat

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 capitol and, to its right, the dome of the Naval Academy Chapel, but not much else—no skyscrapers here. You’ll want to head into the harbor and aim for the domes. If you are coming from the south, be sure to honor the Tolly Point Shoal buoy (green “1AH”). If you are coming from the north, do the same for the Greenbury Point Shoal (red “4”). Other than that, just watch out for crab pots and cross-traffic. Oh yes and sailboat races—it’s not polite to power through the fleet. Anyway, you’ll be fine.

Now it’s time to choose a creek.

Back 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 Annapolis Harbor, 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 city’s largest marinas, fuel, repairs and the Annapolis Maritime Museum. On the west side, you can get a quiet slip at a resort-style marina like Port Annapolis Marina or Annapolis Landing; arrange for any conceivable kind of work for your boat at Bert Jabin’s Yacht Yard; or drop the anchor or pick up a city mooring ball. On the Eastport side, you can choose either a resort marina (Mears), a working marina (Eastport Yacht Center) or scenic Horn Point Harbor Marina.

Spa Creek

The entrance to Spa Creek is straight forward, 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. 

If you head generally for the Naval Academy Bridge over the Severn River until you’ve cleared Horn Point Light “HP”, you can then turn to port, entering Spa Creek with the Naval Academy bulkhead to starboard and Eastport Yacht Club, Severn Sailing Association, and the neighborhood of Eastport on your port side. Don’t even think about cutting inside the “HP” marker unless you are in a kayak or on a paddleboard. 

On the Eastport side, before the Spa Creek Bridge, you’ll find several marinas, most importantly Annapolis City Marina, which has fuel. Beginning in September  2019 you will find a new array of transient slips at South Annapolis Yacht Center 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 (since 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. Think of cruising through the local drive-in with your cherry 1965 Chevy for the benefit of the admiring crowds and you’ll have just the right idea. But you can also 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 feel as if you are now one of the tourist attractions, and you’ll be in the middle of everything, a few steps away from Main Street and the Naval Academy. Annapolis City Dock operates both the Ego Alley slips and all of the city’s mooring balls.

There are a few more city mooring balls on the far side of the bridge, as well as a few places to drop the anchor farther up Spa Creek. To get ashore, call a water taxi or use one of the city’s many dinghy docks.

If you are trailering in

Arriving by car with a trailer in tow? Put in at Annapolis’s Truxton Park near the headwaters of Spa Creek and you won’t go wrong. The ramps are paved and there are good launch docks. ($10 round trip via honor box or  Now head out Spa Creek, and you’ll pass through some of the city’s most pleasant neighborhoods along the way. 

If you plan to leave the boat at a marina, you’ll want to scan the Marina section under Where to Stay for some suggestions. If you’re not planning to stay on the boat, look through the Hotel and Bed & Breakfast section as well.

If you are bringing your paddle-craft

This is a paddler’s paradise, with dinghy docks at the end of nearly every street and parks, such as Truxtun on Spa Creek, where you can put in and easily leave your car. 

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 maritime museum and try out a few restaurants.

Kayak and paddle board rentals are offered by Annapolis Canoe & Kayak, Kayak Annapolis, and Capital SUP.

We’re not crazy enough to try to list all of the possibilities for slips and lodging in Annapolis. Instead, we’re going to give you just a few of our favorites. There are plenty more good ones around.


Back Creek

Annapolis Landing Marina

In addition to slips, a pool, lovely landscaping and all the usual amenities, Annapolis Landing boasts the creek’s only fuel dock. Access is easy with a long T-head for gas and diesel. The marina is on the south side of Back Creek, just beyond Annapolis Sailing School and Port Williams Marina.

Port Annapolis Marina

This popular marina 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. It even has a cottage for those who’d like to sleep ashore. It’s so beautiful that people get married here.

Bert Jabin’s Yacht Yard

Lying along the south side of the upstream Back Creek, Jabin’s is Annapolis’s largest marina and its most complete working yard, with dozens of marine contractors on site—riggers, painters, fiberglass repair, marine electricians and mechanics.

Mears Annapolis Marina

Mears Marina is located on the Eastport side of Back Creek, which makes it an easy walk to restaurants, the maritime museum and downtown Annapolis. Like Annapolis Landing and Port Annapolis across the creek, Mears is lovely to look at and easy to enjoy. In addition to the usual amenities, it offers good tennis courts.

Horn Point Harbor Marina

Without a doubt, Horn Point Harbor has the best view of all the Back Creek marinas since it overlooks the Bay from its position at the mouth of the creek. That location, however, also makes it more susceptible to winds and chop, depending on the direction, though its breakwater takes care of most of the rough water. Like Mears, Horn Point Harbor is an easy walk to Eastport’s restaurants and points of interest.

Spa Creek

Annapolis City Marina

This is one of two marinas with fuel docks on Spa Creek. Slips are a little tight, but the location is terrific. Eastport restaurants, including Carrol’s Creek and the world-famous Boatyard Bar & Grill (voted best crab cake in the area) are only a few steps away. Downtown Annapolis is just across the Spa Creek Bridge.

Annapolis Yacht Basin

This is the other marina on Spa Creek with a fuel dock. This is also the marina where you’ll find the mega-yachts in port at any time. But there is room for boats of all sizes. The location is lovely, on the downtown side, next to the Annapolis Yacht Club.

Annapolis City Dock

Depths are good, the fairway (Ego Alley) is narrow, but the location for visiting historic downtown Annapolis couldn’t be better. Annapolis City Dock also operates 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’s. Prices on Ego Alley are slightly better during non-weekend, non-holiday periods.

Hotels and Bed & Breakfasts

Here are just a few of our favorites for both downtown and Eastport.

Annapolis Waterfront Hotel

Annapolis Waterfront is the only hotel and the only restaurant (Pusser’s Caribbean Grill) directly on Ego Alley, which makes it ideal for sightseeing trips and for watching the passing scene while sipping a refreshing Painkiller rum drink. Not surprisingly, the hotel comes alive during the fall boat shows.

Inn at Horn Point

The Inn at Horn Point dates to 1902 and features charming rooms with their own balconies. The location is within quiet Eastport.

Historic Inns of Annapolis

Here’s a chance to stay in the midst of famously historic Annapolis in one of three period inns, all close to State Circle, restaurants, shopping and the city’s famous and narrow, 18th century streets.

Flag House Inn

This delightful bed & breakfast is located in a restored Victorian, just across the street from the pedestrian entrance to the Naval Academy and an easy walk to the water, shopping and everything else.

Gibson’s Lodgings

Gibson’s is a 21-room, completely charming townhouse hotel located between the Naval Academy and City dock. It is actually made up of three 17th and 18th century homes and features a central courtyard.

Water Taxi

You have several options for getting around Annapolis, from Back Creek marinas to Eastport restaurants and City Dock shops and sites. One of the easiest is to make use of the Annapolis Water Taxi service ($3-$8 one way depending on destination). If you are anchored or on a mooring ball, simply call them on channel 68 or give them a call at 410-263-0033.

Dinghy Docks

In some distant past, the city planners had the foresight to put dinghy landings at the end of many of the streets ending on both Spa and Back creeks—about 20 in all. Unfortunately, a number of these have fallen into disrepair, but happily a good number survive to provide a handy place to park. So, if you are anchored, on a mooring ball, at a marina, or have a trailer boat 12 feet or less, you can make use of this unique Annapolis feature. The size restriction for Ego Alley’s dinghy landing is 17 feet.

Several decades ago—a drop in the bucket Annapolis-history-wise—the Spa Creek Bridge was closed for a while. This effectively separated Eastport from the old downtown, so Eastporters decided to form their own republic, complete with flag and coat of arms, which, among other things, featured a Chesapeake Bay Retriever rampant with a tennis ball. The bridge re-opened, but the spirit of revelry and revolution continued, with a tug of war battle against Annapolis proper and a 0.5-K charity race across the bridge held annually. Originally a farming community and a waterman’s settlement, Eastport retains its own spirit. With that in mind, here is a short tour that we feel will give you the spirit of the place. Don’t worry, that spirit includes plenty of spirits, lots of food, and a bit of history.

If you are here on a Wednesday through Sunday, we suggest you start the morning with coffee and homemade pastries at Bakers & Co. on Chesapeake Avenue (they have scrumptious soups too) or on any day of the week at Leeward Market Café on Second Street.

Now that you’re ready to face the day, spend some time wandering up and down the streets of Eastport, which are chock-a-block with charming and sometimes eccentric homes as well bushels of flowers and shrubs. When you’ve worked your way back to Second Street, stop for a visit at the remarkable Annapolis Maritime Museum located in Eastport’s last oyster house. If you dawdle until it’s time for lunch, we suggest you head a few blocks up Chester Street to Davis Pub, the peninsula’s only dive (and a CBM staff favorite). There you can sit outside with your dog and enjoy this quintessential neighborhood pub. Order a crab pretzel and a cold craft beer.

Alternatively, just behind the museum you’ll find Wild Country Seafood, operated by Eastport’s last watermen. They rise early to work their pots then bring back their catch to sell. Crack a dozen crabs at an outdoor table as you watch Back Creek lap up against the tiny museum beach. Heaven!

After lunch, grab a water taxi back to your boat or lodging or simply find a bench at the end of nearly any street in Eastport and sit and enjoy the water. When you are ready for a special meal out, walk over to Severn Avenue, where you’ll find the finest hunk of meat in town at Lewnes Steak House, or make it a seafood excursion at O’Leary’s Restaurant, or catch an Uber over to Sam’s on the Waterfront at Chesapeake Harbor for an award-winning meal. We recommend getting reservations for these popular outings. On Wednesday summer nights, walk another block or two up Severn to Carrol’s Creek Restaurant and watch the races finish at the foot of Spa Creek Bridge. For lunch, dinner or Sunday brunch, be sure to visit the local sailor and angler gathering place voted the area’s best crab cake, best raw bar, and most family friendly—the Boatyard Bar & Grill. That’s where Jimmy Buffet goes when he’s in town. It’s on Severn Avenue too.

There is so much to do in downtown Annapolis, it will be hard to choose. So, instead of a simple list of things to do and places to eat, here too we’ve put together a proposed itinerary for downtown that includes shopping, historic sites, and enough food and ice cream to keep you going. Oh, and don’t forget to pack your favorite walking shoes or flip-flops. You’re going to thank us later.

After breakfast at someplace like the remarkable Iron Rooster, 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. Pick out a souvenir Annapolis hoody for Uncle Bob back home. When you reach Church Circle, admire the lovely and historic St. Anne’s Parish and its graveyard before turning left to explore West Street’s shops, galleries and restaurants. West Street is where you’ll find some of the city’s hottest venues, from the Ram’s Head Stage and Tavern to 49 West Coffee and Wine Bar. On West Street, you also find the Annapolis Visitor Center, where many of the city tours begin and you can pick up more brochures than you can possibly juggle.

Now turn around and head over to State Circle for a tour of the hyper-historic State Capital building, which the very place where George Washington gave his Farewell Address when Annapolis was briefly the nation’s capital. On the circle, you’ll also find more restaurants and and shops.  You’ll want to stop here at Paws Pet Boutique to pick up that pink beach buggy collar Fido has been been begging for. You’ll find yet more cool shops and restaurants down Maryland Avenue. Browse through Old Fox Books and enjoy a pint at Galway Bay Irish Pub before gathering up the final burst of energy necessary to wend your way back to the water through the town’s maze of narrow brick streets. Don’t forget to admire the city’s world-class collection of 18th century architecture as you go. Watch your step, though, the 18th century wasn’t famous for smooth pavement. 

Now treat yourself to lunch at the new Market House or historic Middleton Tavern or do “breakfast all day” at the Iron Rooster. Or Sofi’s Crepes. Or Mission Barbeque. Or Pip’s Dock Street Dogs—the best cheesesteak south of Philly… so many choices!

Feeling revived? Then this is the time to stroll over to the U.S. Naval Academy visitors entrance and take in its fine museum and exquisite ship’s models. On your way to the visitor’s entrance, be sure to pop into the award-winning Annapolis Marine Art Gallery on the corner of Dock and Craig streets, which provides collectible art and gifts including prints and originals by John Barber, Patrick O’Brien, Willard Bond, John Stobart, Paul Landry, John Ruseau and other notable artists. 

You’ll have just enough time for a quick refresher at one of Annapolis’s great ice cream shops. Our CBM Ice Cream editor particularly recommends the Annapolis Ice Cream Company before you set sail on a sunset cruise aboard one of the two beautiful schooner Woodwinds from city Dock at Pusser’s Grill. (Storm Bros Ice Cream Factory on Dock Street is the other excellent choice.) Finish the evening with an elegant dinner at Harry Browne’s on State Circle or local seafood bouillabaisse at Café Normandie. After dinner, take a stroll up to the Drummer’s Lot Pub in the historic Maryland Inn for a nightcap before tucking in for a good night’s sleep. You’ve earned it!

The next morning, head back up Main Street for breakfast and the traditional Pledge of Allegiance at kitsch-rich Chick and Ruth’s Delly or go further up Main Street and farther back in time for breakfast at the elegant and delicious Treaty of Paris Restaurant.

Now take a final stroll through town and enjoy a coffee at City Dock Coffee before climbing aboard, or loading up the trailer, and heading back to your home port. Whew. Sure you’re exhausted, but you’ll have had a weekend on the water very well spent. ⚓︎