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Weekends On the Water

Photo by Betsy Kehne.

Destination: Annapolis 

By Jody Argo Schroath 

WHY YOU SHOULD GO 

No matter 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? We’ll explain how to negotiate busy Annapolis Harbor without hassle to find your slip with ease and enjoy a weekend to remember (and how to get onto the water just as easily if you don’t own a boat). 

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! 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. 

WHAT YOU CAN EXPECT TO FIND 

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 some of its fanciest marinas, as well as 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 on any number of dinghy landings throughout the two creeks. 

HOW TO GET THERE 

If you arrive by boat 

Annapolis Harbor lies just south of the 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—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 mouth of the river, 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, 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 Yacht Yard; or drop the anchor or pick up a city mooring ball. On the Eastport side, you can choose either a resort marina (Safe Harbor Annapolis, formerly known as Mears), a working marina (Eastport Yacht Center) or the previously-mentioned Horn Point Harbor Marina

Spa Creek 

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.  

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 ClubSevern 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. You may also want to check out transient slips at the new South Annapolis Yacht Center offers 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. It’s like cruising through the local drive-in with your cherry 1965 Chevy for the benefit of the admiring crowds. 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 AcademyAnnapolis City Dock operates both the Ego Alley slips and all of the city’s mooring balls. More dockage is available at Annapolis Town Dock, at the former Fawcett’s location. 

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 annapolisparking.com).  Now head out Spa Creek, and you’ll pass through some of the city’s most pleasant neighborhoods along the way.  

If you are bringing your paddlecraft 

This is a paddler’s paradise, with dinghy docks at the end of nearly every street and parks, such as Truxton, 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 Paddle AnnapolisAnnapolis Canoe & Kayak, and Capital SUP.  

WHERE TO STAY 

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. 

Marinas 

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 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. 

Safe Harbor Annapolis 

Formerly known as Mears Marina, Safe Harbor 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, Safe Harbor Annapolis is lovely to look at and easy to enjoy. In addition to the usual amenities, it offers a pool, as well as tennis and pickleball 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 Safe Harbor Annapolis, 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. Prices on Ego Alley are slightly better during non-weekend, non-holiday periods. 

Annapolis Town Dock 

Managed by Oasis Marinas in the former Fawcett’s location, this 228-foot strip of dockage puts you right next to Pusser’s and the Fleet Reserve water taxi on the infamous Ego Alley. It’s an easy walk to Main Street, USNA and other historic sites. Use Snag-a-Slip for reservations. 

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 Grille) 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 is a boutique bed and breakfast set in the eclectic neighborhood of Eastport. It has recently moved around the corner to a new location, still in Eastport, at 534 Burnside St., where they serve regionally-famous breakfasts. 

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 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 of Annapolis 

Gibson’s Lodgings is a 21-room, completely charming historic inn located between the Naval Academy and City Dock. It is actually made up of three houses from the 17th, 18th and 19th centuries. The homes feature a central courtyard. 

HOW TO GET AROUND 

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 ($4-$9 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 22 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. Boats may not be left on public docks for more than two consecutive nights. The size restriction for Ego Alley’s dinghy landing is 17 feet. 

WHAT TO DO IN
THE MARITIME REPUBLIC OF EASTPORT 

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/Eastportericans decided to form their own republic, complete with flag and coat of arms, which, among other things, featured a Chesapeake Bay Retriever 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 watermen’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 weekend, 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 & Grocery on Second Street. You also can’t go wrong popping into Bread and Butter Kitchen, on the waterfront side of Second Street, for breakfast or lunch. 

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 as 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 & Park 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 Bay Weekly staff favorite). There you can sit outside with your dog and enjoy this quintessential neighborhood pub with a crab pretzel. For beer enthusiasts, be sure to visit Forward Brewing on Fourth Street, the first nano-brewery in the neighborhood. 

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 Steakhouse, or make it a seafood excursion at O’Leary’s Seafood, or at Eastport favorite Blackwall Hitch, which opened in 2014 by James King, restaurateur and CEO of Titan Hospitality. King wanted the restaurant to feature a nautical-inspired dining theme that would blend the area’s finest in tastes and talents. Seasonally driven and locally sourced food and spirits, local music and friendly staff greet you upon arrival. Reservations are recommended 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.  

WHAT TO DO IN HISTORIC ANNAPOLIS 

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, 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. 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. If art makes your heart soar, be sure to stop in McBride Gallery, the largest gallery in historic Annapolis. 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 on Stage to 49 West Coffeehouse 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, 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 shops, with even more down Maryland Avenue. Browse through Old Fox Books where you can enjoy a cup of java from Brown Mustache coffee, or sample a pint at Galway Bay Irish Restaurant and 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  Annapolis Market House or historic Middleton Tavern. Or Sofi’s Crepes. Or Mission BBQ. 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 (which reopens to the public this weekend, from sunrise to 7pm, photo ID req’d, visitors will be screened and bags checked) 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.  

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 a beautiful schooner with Schooner Woodwind, which runs sailing cruises from the Annapolis Waterfront Hotel. (Storm Bros Ice Cream Factory on Dock Street is another excellent choice.) You could also choose to do a Watermark tour or cruise to catch the spots you didn’t see the first time around. 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 Chick and Ruth’s Delly. Now take a final stroll through town, enjoy a coffee from Bitty and Beau’s or Rise Up (inside Market House), 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. ⚓︎ 

A few of our favorite places… 

Annapolis School of Seamanship 

Learn how to properly operate your boat, earn your captain’s license, brush up on skills or bring your kids to become junior captains with on-water lessons. Classroom topics also include diesel engines, electrical systems, navigation, safety and weather. ASOS is currently operating at the Annapolis City Marina, Suite 206, 410 Severn Ave., Annapolis. Contact: 410-263-8848; https://www.annapolisschoolofseamanship.com/ 

Annapolis Sailing School 

Always wanted to learn how to sail? Annapolis Sailing School is the place to learn sailing “the Annapolis Way” — which means fun and relaxing. Classes available for all ages and all skill levels. They also offer kids camps, teaching them to control their boats in a safe but fun way. 7001 Bembe Beach Rd., Annapolis, 410-267-7205;  http://www.annapolissailing.com/ 

Galway Bay Irish Restaurant and Pub 

If a pint of Guinness and live music sound like heaven to you, then step into this pub and transport yourself to the Emerald Isle without ever leaving town. This downtown restaurant also offers the best whiskey experience in the Americas, so says Irish Hospitality Global. For summer, they have turned their famous Galway Bay Irish Egg Nog into ice cream, available in 12 ounce to-go containers or try one of their new summer cocktails like Bertha’s Revenge, Aperol Spritz, Blackberry Beret, or a West Cork Lemonade (ages 21+ only). Sidle up to the bar—which was built in Ireland and shipped to Annapolis, where six Irishmen installed the dark wood custom bar with glass shelving—and let your worries evaporate. 63 Maryland Ave., Annapolis, 410-263-8333; http://www.galwaybaymd.com/ 

O’Brien’s Oyster Bar & Seafood Tavern 

With a seafood menu sourced straight from the Bay, this restaurant has a long history on the Annapolis waterfront. Built in 1774, as the Rose & Crown, this tavern was once a local gathering spot for both Royalists and Revolutionaries. Today it’s best known for its oysters and happy hours. It’s an excellent spot for brunch, drinks and people-watching. 113 Main Street, Annapolis; https://www.obriensoysterbar.com/ 

Annapolis Ice Cream Company 

A repeat winner of CBM Bay Weekly’s Best of the Bay for ice cream shop, this icon of downtown known for inventive flavors now has an ice cream truck to make summer even sweeter. Check out their frozen works of art on their social media pages, too. 196 Main St., Annapolis, https://annapolisicecream.com/ 

Blackwall Hitch 

This upscale-casual New American restaurant is well situated in Eastport, with outdoor seating, an on-site pub & stylish decor. Executive chef David Montenez has more than 15 years’ experience in upscale dining and lends his expertise to the coastally-inspired menu. 400 Sixth St., Annapolis, 410-263-3454www.blackwallhitchannapolis.com/ 

McBride Gallery 

Promoting artists and their creations is work owner-artist Cynthia McBride loves, as is meeting customers. She credits her long and enduring presence on Main Street to listening to what customers need. Now she runs the largest art gallery in historic Annapolis. 215 Main St., Annapolis, 410-267-7007, www.mcbridegallery.com