Exploring the Chesapeake Bay

By: Charter, Cruising Tips, Destinations

Exploring the Chesapeake Bay During the Arabella Cruise

By Gwen Mayes

American Sailing has partnered with the Manhattan Yacht Club to offer charter cruises on Arabella.  This month ASA Members were on Arabella cruising the Chesapeake Bay. Aboard the vessel was Gwen Mayes, a writer and local expert who lent her expertise and local knowledge to the voyage. She put together this exploratory guide to the region for all ASA Members.

The Chesapeake Bay is the largest estuary in the United States; the third largest in the world.  It runs nearly 200 miles long and including all its tributaries is only an average of 21 feet deep.  Formed millions of years ago by the flooding of the Susquehanna River during melting of the ice in the Ice Age, the rich history of the Chesapeake has been shaped by the explorers, Native Americans, colonists, and watermen who made a sustainable life working on the water.  These men are called “watermen” and they crab, fish, and harvest oysters depending upon the ever-changing natural elements of rain, wind, tides, and the flow of water.  The watershed area of the Bay is 64 thousand square miles and includes six states and the District of Columbia.  

The Chesapeake Bay is a delicate ecosystem like none other in the country.  Eastern oysters were so plentiful in the early 1600s shorelines appeared as crystal clear as modern day aquariums. In late 1800s, over 15 million bushels of oysters were harvested annually for distribution as far as Iowa.  Little was known at the time about their importance to the overall health of the Bay as one oyster can filter up to 50 gallons of water per day.  

Today, less than 1% of the oyster population remains. The health of the Bay is in question, constantly monitored by the University of Maryland Center for Environmental Science.  The depletion of Maryland’s oyster stock – and resulting decline of the cleanliness of the Bay – can be attributed to several factors, including overharvesting oysters, habitat loss, and parasitic disease. The degradation of the Bay’s water quality is another important factor. As land throughout the Chesapeake Bay watershed has been developed from rural, forested landscapes that act as natural filters for stormwater entering the bay to urban and suburban areas, an excess of nutrients and sediment has flowed freely. The influx of nutrients can cause “dead zones,” or areas of low oxygen, which make it hard for oyster larvae to develop. Moreover, increased sediment in the Bay may suffocate otherwise healthy oysters, and those that are weakened may become more susceptible to disease, as discussed below.

Every city visited on the tour has a unique history and importance to the heritage of the area and the livelihood of the 18 million people who live within one mile of its shoreline.  It’s important to remember, however, that the environment and sustainability of the Chesapeake Bay are directly related to the love of living on the water, tending to the water’s natural habitat, and respecting the local people who call the Chesapeake Bay home. 

Discover the Chesapeake Bay


City Dock – During the US Sailboat Show , the hub of Annapolis, City Dock, is transformed into an arena of boating mania.  Virtually every aspect of boating is represented from safety gear to nautical maps, to the latest mega yachts you can tour (wear comfortable shoes that easily slip off; you’ll leave them on the docks).   It’s recommended that you obtain tickets in advance.  Expect large crowds.  

When you’re on City Dock you’ll recognize that Annapolis is a relatively unchanged historic city. During colonial times, Annapolis was the center of commerce for Maryland but after the Revolutionary War, Annapolis’ harbor lost its stronghold to Baltimore which become more popular due to its larger and deeper port. Because of this, Annapolis’ smaller-scale waterfront has remained relatively intact and did not develop the warehouse and industrial complexes that crowded Baltimore’s waterfront. During the late 1800’s Annapolis maritime industries were focused on commercial fishing and oystering, and the shoreline was packed with working boatyards, seafood processing plants, and fuel docks. Downtown Annapolis remained mainly a working waterfront until the 1970’s when the oyster industry crashed after years of decline and the recreational boating industry took over.

Annapolis Maritime Museum located at 723 Second Street in Eastport (a peninsula off the Annapolis Harbor), is housed in the former McNasby’s Oyster Packing plant, the last oyster packing plant in full operation in the Annapolis area.  A permanent exhibit, “The Changing Waterfront” opened in 2021 with three thematic sections:  1) the ecosystem of the Chesapeake Bay and the health of the Bay; 2) oyster harvesting with hands-on tongs, dredges, and a holographic waterman explaining his craft; and 3) the changing Annapolis waterfront with historical recordings from boatbuilders such as John Trumpy Sr. who built luxury yachts for the DuPonts and Rockefellers, and the construction of subchasers for the Navy.  Parking is limited; walking from City Dock takes about 30 minutes or is accessible from the Water Taxi 410-263-0033 (tell the skipper you want to go or be dropped off at the Annapolis Maritime Museum on Back Creek).  www.amartime.org 

Chesapeake Bay Bridge –  As part of cross-country US 50, the Chesapeake Bay Bridge connects the Baltimore-Washington Metropolitan Area with Ocean City, Maryland, Rehoboth Beach, Delaware, and other coastal tourist resort destinations. As part of US 301, it serves as part of an alternative route for Interstate 95 travelers, between northern Delaware and the Washington, D.C., area. Depending upon where you measure it is reported to be 2-4 miles long.  When the first span opened in 1952 it was both the longest continuous over-water steel structure and the third longest bridge in the world. Because of its height, the narrowness of the spans, the low guardrails, and the frequency of high winds, it is known as one of the scariest bridges in the world.

Greenbury Point Towers – The “Eiffel Towers” that appear at the edge of Annapolis Harbor at the entrance of Severn River are the Greenbury Point Towers.  The first colonial settlement in this area was at Greenbury Point, but later those settlers moved to where Annapolis is now, for better protection from storms and the southerly winds. The cables were wrapped around the towers, creating a loop. The towers sent out low-frequency waves since they can travel through water, allowing the Navy to communicate with submarines up to 65 feet below the surface. They provided centralized communication during World War I and World War II for land to sea communication.  Today, 3 towers remain, and all have different functions. One is a cell tower, one is kept for historic reasons, and the other is for radio communication. It has become a popular hiking destination for nature lovers, runners, walkers, and dog walkers. While the Navy allows public access to the conservation area when safe to do so, the area is also critical to the NSA Annapolis mission and can close anytime without prior notification.

US Naval Academy — The United States Naval Academy was established on October 10, 1845, under Secretary of the Navy George Bancroft. Over 340 acres, the Academy is located on the former grounds of Fort Severn. The entire campus is a National Historic Landmark and home to many historic sites, buildings, and monuments. In 1941, the land that made up the Hell Point neighborhood was acquired, and dozens of homes were demolished as part of the Academy’s expansion during World War II following the bombing of Pearl Harbor. The Academy brigade is approximately 4500 men and women who attend one of the top public colleges in the US prior to their selection of a naval career or entering the US Marines. The Chapel is the recognizable copper dome on the city’s skyline.  The best way to truly experience the U.S. Naval Academy is to take one of our highly-regarded historical USNA tours. Led by professional, passionate, certified guides, these tours bring many of the U.S. Naval Academy’s most important stories to life. Take a public guided walking tour to hit the highlights and get the inside scoop on admissions and the midshipmen experience. Public tours are highly recommended.  https://www.usna.edu/homepage.php 

Where To Eat in Annapolis

Annapolis Restaurants – will be packed; make reservations in advance when possible.  

On the EASTPORT side (walkable across the drawbridge over Spa Creek; close to the harbor) 

  • Boat Yard Bar and Grill — sailors hangout, wide menu, ‘diner’ type food, they also serve great breakfast and best crab cakes in town; expect a wait but always great folks to kill the time with
  • Davis’ Pub — local hangout, best burgers, crab pretzel, steamed shrimp, local seafood, great atmosphere, family-friendly (on Back Creek at 4th Street  https://www.davispub.com/ 
  • Blackwall Hitch — little pricier, located right at the Spa Creek Bridge (6th street), upstairs outdoors dining, family-friendly, music at night  (they take reservations) https://www.blackwallhitchannapolis.com/ 
  • Carol’s Creekside Cafe — institution — most popular spot in the area and worth every penny; great harbor views and views of USNA; white tablecloths; expensive; great outdoor dining; reservations are a must https://carrolscreek.com/ 

My favorites on the ANNAPOLIS HARBOR side of the Spa Creek Bridge 

  • Iron Rooster — crazy menu, great breakfast, waffles, burgers, family fun, limited reservations, outdoor seating; think waffles and chicken https://iron-rooster.mailchimpsites.com   
  • Mission BBQ — Probably isn’t what you get in Memphis but for a chain restaurant it’s good; get ‘to go’ and you find a spot to sit and watch the boats.  
  • Harry Browne’s – at Capitol Circle overlooking the Maryland State Capitol, the longest continuously operating state legislative body in the US https://www.harrybrownes.com/   
  • Middleton Tavern — The 18th-century Georgian building contains little bits of history on its walls, such as Civil War muskets, old Naval Academy uniforms, nautical-themed pictures, and classic Maryland landscape paintings. Enjoy an open-air café during the summer. Part of the Tavern’s year-round popularity lies in the fact that you don’t often get a chance to eat in a 250-year-old building. http://www.middletontavern.com/about.html 
  • Osteria 177 – https://www.osteria177.com/ From the elegant atmosphere to the freshest ingredients that comprise his dishes, Arturo is passionate about every aspect of Osteria 177. A gastronomical delight, the culmination of the finest ingredients from sushi-grade ahi carpaccio to Fell’s Point Beef creates a fine dining experience unlike any other. Upscale Italian dining; small bar area.  Original paintings decorate the walls as the glittering chandeliers light the modern art deco style.

Calvert County – Solomon’s and Calvert Cliffs 

Solomons is located at the southern tip of Calvert County. The town is small and unadorned from a commercial perspective; however, small arts and craft stores are plentiful.  It is a lovely spot with a boardwalk right on the Patuxent River (one of the 150 rivers that flow into the Bay).  Lovely craft shops, pubs, and fisheries line the boardwalk.  Solomons, also known as Solomons Island, is an unincorporated community and census-designated place. The population is close to 3,000, up from 1,536 in 2000. Solomons is a popular weekend destination spot in the Baltimore–Washington metropolitan area.

Calvert Marine Museum is open daily from 10 a.m. to 5 p.m. It is a short (15 minute), flat walk from the harbor to the museum (depending upon where you disembark).  It is an excellent source of maritime history explaining the development of the Calvert Cliffs, and the shipbuilding industry that remains active today.  Also, at the museum is one of the four screw-pile, cottage-style lighthouses on the Bay – the Drum Point Lighthouse.  https://www.calvertmarinemuseum.com/ 

Annmaire Sculpture Garden & Fine Arts Center requires a 20-minute taxi ride outside the city but is worth the trip.  It features art inside and outside with many sculptures lining a wooden path.  Much of the art,  sculptures and carvings are on loan from the Smithsonian Museum.  The art lab onsite has changing exhibits.  https://www.annmariegarden.org/annmarie2/ 

Restaurants – 

  • Lighthouse Restaurant and Dock Bar.  Specializing in Caribbean food; e.g., jerk chicken, spicy wings, mojitos and shrimp tacos; great sunset viewing https://www.lighthouserestaurantanddockbar.com/ 
  • The Island Hideaway — A family-owned & operated restaurant offering an assortment of fresh New American Cuisine ​on Solomons Island; top choice of locals; try the Crab Cake Dinner or Mom’s Mac-n-Cheese.  http://www.theislandhideawaysolomons.com/  Check hours on website; closed Mondays.  
  • The Pier Restaurant — https://thepiersolomons.com/ a lively outdoor bar with stunning sunsets that spans the Patuxent River; go for the Black and Blue Crab Cake NY Strip Steak. Open daily till 10 p.m.

Cambridge – Dorchester County

Cambridge is an eminently walkable town founded in 1684.  It is one of the oldest colonial cities in Maryland.  The massive Choptank River connects the town to the Chesapeake Bay.  It has a rich maritime history of building boats, sailing schools, and watermen experienced at catching crabs, dredging for oysters, and other seafood.  The Dorchester Visitor Center, 2 Rose Hill Place is locally known as SailWinds and recognizable by the large white sailing sail positioned over the building.  

Blackwater National Wildlife Refuge is the at the natural heart of Dorchester County. It is 28,000 acres of brackish marshes, pine hammocks, and hardwoods, one of the Chesapeake Bay’s epicenters for bald eagles as well as beautiful, formerly endangered fox squirrels, wintering migratory waterfowl, and a host of other birds.  There’s a visitor center for bird-viewing, a wildlife drive, and several short hiking trails. The hiking trails are open daily dawn to dusk.  Bring insect repellent and the trails can get soggy after heavy rains.  To visit will require transportation (UBER or cab) approximately 30 minutes south of Cambridge. https://www.fws.gov/refuge/Blackwater/ 

Harriet Tubman Underground Railroad replicates the challenges of freedom fighters, where they grew up, and most astonishingly where they risked their life.  Harriet Tubman returned again and again to usher 70 family members, friends, and other enslaved people across the Mason-Dixon line along a network to freedom known as the Underground Railroad.  While in Cambridge you can visit the Harriet Tubman Museum while in Cambridge.   https://visitdorchester.org/harriet-tubman-museum-educational-center/ 


  • Snappers Waterfront Café and Tiki Bar is at 112 Commerce Street in Cambridge.  Watch local sailors and watermen working on schooners, tugs, bugeyes, and skipjacks.  It features a wide range of American, Southwestern and island cuisine.  Sit at a high top, sing along, get sand in your shoes.  Late night spot for local flair.  It’s worth noting that their Maryland blue crab meat is delivered from the JM Clayton Company right next door – often still warm from being picked.  So “yes” they appreciate fresh seafood! https://www.snapperswaterfrontcafe.com/ 
  • THEO’s Steaks and Spirits – a high-end white-table cloth, can’t be beat steakhouse.  Easy walk from the city marina, just up the brick street lined with old oak trees.  Closed Monday and Tuesday.   https://theossteakhouse.com/cambridge%2C-md 
  • Momma Maria’s – hands down the best restaurant in Dorchester County; however, getting there is a challenge.  https://www.mommamariasbistro.com/  Mediterranean Bar and Grille located in Trappe, MD less than 10 miles north of Cambridge in a town so small you will miss it if you blink.  Whether you’re in the mood for a beer and wings or a glass of Cabernet and a filet mignon— at Momma Maria offers something for everyone.
  • Ava’s Pizzeria and Wine Bar – 543 Poplar Street; fresh mozzarella, fire-oven pizzas, homemade meatballs (try one with a traditional salad; they’re as big as softballs).  https://avaspizzeria.com/cambridge%2C-md 

St. Michaels and Talbot County

Arabella from the Inn at Perry Cabin

Considered by most as the “gem” of the Chesapeake Bay’s Eastern Shore, St. Michael’s is a charming town, easily walkable with wonderful jewelry stores, shipbuilding warehouses, upscale fashion shopping, elegant dining, and waterside crab shacks.  The majestic harbor is a popular spot to congregate late in the day for dinner or drinks.  The main street – Talbot Street—will connect you to most of the shops and locations to visit.  Everything you need is walkable.  

Guildford & Company – a fine jewelry antique and estate store with vintage nautical jewelry and finery; 101 North Talbot Street. Open every day.  http://guilfordandcompany.com/ 

Chesapeake Bay Maritime Museum is a must-see in St Michael’s.  213 North Talbot; open daily 10-5.  The property contains sheds and boat building warehouse, exhibits for log canoes, racing gear, and classic automobiles. Each day offers something unique–get your hands wet exploring a waterman’s shanty, talk with a shipwright or visiting captain about his or her work or vessel, and be sure to climb to the top of the historic 1879 Hooper Strait Lighthouse for the best view of St. Michaels’ harbor and the Chesapeake’s Miles River  www.cbmm.org 

Shore Pedal and Paddle to rent kayaks, and bikes. www.shorepedalandpaddle.org 

Inn at Perry Cabin – former summer home of Laura Ashley and location site of the movie Wedding Crashers, an elegant, spacious property on the Miles River with a wonderful spa, outdoor dining, pub with fireplace, and relaxed (but elegant) atmosphere.  https://innatperrycabin.com/ 

Lyon’s Rumhttps://www.lyonrum.com/ Founded in 2012, the distillery has a signature line of rums paying tribute to the rich, spirited traditions of the Eastern Shore. LYON RUM starts with intentionally sourced raw ingredients: 100% Louisiana cane sugar & molasses, and is truly hand-crafted – mashed, fermented, and double-distilled in small pot stills – every step of the way, resulting in a wonderfully unique final product.  The tasting room is open noon to 6 p.m.  


  • Ava’s Pizzeria and Wine Bar – same owners as the one in Cambridge, MD; fresh mozzarella, fire-oven pizzas, homemade meatballs (try one with a traditional salad; they’re as big as softballs).  
  • Foxy’s Harbour Grille – for those interested in island living, outdoor bands and a remake of the flagship restaurant in the BVIs.  https://www.foxysharborgrille.com/ 
  • The Bistro — Fine food, meticulously served in a warm, friendly atmosphere.  https://bistrostmichaels.com/ 
  • Limoncello – Located in the heart of St. Michaels, Limoncello Italian Restaurant and Wine Bar serves up authentic and approachable favorites for lunch and dinner daily. You will find an incredible diversity of grape varietals and an amazing selection of exclusively Italian wines by the glass. 200 South Talbot Street.  Open for lunch daily 11-4.  http://limoncellostmichaels.com/ 


Arabella Pulling Into Baltimore

The National Aquarium is in the heart of downtown Baltimore on the Inner Harbor, easily accessible by all modes of transportation.  https://aqua.org/visit  Visit the Shark Catwalk, view the Dolphin Tank, and experience life underwater through a 4D experience. Catch a critter chat, get up close with an ambassador animal, watch a puffin feeding, learn more about dolphins from marine mammal experts and more with daily activities! Allow 2-3 hours to fully appreciate all that is offered in the museum.  

Fell’s Point is one of the oldest neighborhoods in Baltimore, Fell’s Point was once a bustling shipbuilding port. Its visage has remained largely unchanged since its founding—picture Belgian block streets, waterfront restaurants and cozy boutiques just a few blocks east of the Inner Harbor. You can also learn about Fell’s Point’s history as home to the first African American-owned shipyard in the country at the Frederick Douglass-Isaac Myers Maritime Park Museumhttps://baltimore.org/neighborhoods/fells-point/ 

The Gallery at Harborplace – walk around to boutiques, candy stores, hat shops, restaurants, pubs, and people watch on the harbor.  21 stores in all – something for every budget and interest.  200 East Pratt Street (can’t miss it) https://www.thegalleryatharborplace.com/en/directory/ 

Federal Hill Park – Before you visit the National Aquarium, Maryland Science Center, Power Plant and Historic Ships, get a birds-eye perspective of the attractions clustered around the waterfront at Federal Hill Park, a 10-acre, elevated park that was once defended by the city during the War of 1812. Wear comfortable shoes to climb the 99 steps to the top. http://www.federalhillonline.com/ 

Fort McHenry National Monument and Historic Shrine – Built in the shape of a five-pointed star, Fort McHenry defended the city during the Battle of Baltimore in 1814, which inspired Francis Scott Key to pen the Star-Spangled Banner. The informative and entertaining exhibits and ranger programs offer a great history lesson, while the 42-acre park, which juts into the harbor, presents great opportunities to enjoy the outdoors. Walk along the sea wall trail or lounge on a picnic bench next to the water. https://www.nps.gov/fomc/index.htm 


  • Angie’s Seafood – The bar is loud and raucous.  The food is memorable.  http://angiesseafood.com/ The Broiled Fisherman Platter, with shrimp, scallops, crab imperial, and fish is a good way to taste a boatload of seafood. “Strolling past the old five-story brick building on Pratt Street just east of Broadway in Upper Fells Point, our ears were captivated by what, for many Baltimoreans, is our ultimate siren song. Was that—could it be—the familiar crack of the mallet hitting shell echoing inside these long-dormant but once hallowed grounds?” – Baltimore Sun 
  • La Scala in Little Italy – At the age of 9, Nino Germano left Bafia, Sicily to move to Baltimore joining relatives and in search of the American Dream. His father established a successful construction company, but Nino held a strong passion for great Italian food. Under his mother’s tutelage in the kitchen, Nino opened an Italian restaurant and pizzeria, Zia Pina. It was successful enough to open a second location, La Scala. La Scala features an indoor bocce ball court, a large dining room, and a wine tasting room. https://lascaladining.com/about-us/  Open Wednesday through Sunday only.
  • Hersh’s If you’re looking for a cozy spot to catch up with new sailing friends over good food and drinks, Hersh’s is the place. Pizzas come with a charred but chewy crust and unique ingredients, such as kale and pistachio, and clams and lemon. House-made ricotta adds a creamy texture to several standout dishes, including the crostini, ravioli and pizza. 1843-45 Light Street; closed Monday and Tuesday. https://hershs.com/ 
  • Charleston – A homage to low-country cooking from nine-time James Beard Award nominee Cindy Wolf, Charleston has been wowing diners for more than 20 years. Why go? With one of the best wine lists in the city and a prix-fixe menu that explores seafood, poultry and meat with equal panache, Charleston is a local favorite for celebratory meals. 1000 Lancaster Street.  The budget for this restaurant is described as “a blowout”.  Dress accordingly.  Open daily.  https://charlestonrestaurant.com/