Best Places To Go Boating Near Annapolis
There are many reasons to come to Annapolis when it is time to search for your next boat. Sail or power, the variety of quality boats for sale in the Annapolis area is unsurpassed, covering every choice of sleek day cruisers to rugged, all-season voyagers capable of circling the globe. New, used, even timeshare is available.
Besides this large inventory, another motivation to focus on Annapolis is the tantalizing mix of interesting places to visit in Chesapeake Bay. The largest tidal body in North America, the Bay stretches for 200 miles, from the Elk River in the north, down to Cape Charles and Cape Henry in the south. Chesapeake Bay is approximately 4,500 square miles. It is big water but surrounded by coastline.
There are many historic footprints along its shores. The first newcomers to the New World settled in Jamestown, Virginia in 1607. Then, through the growing periods of American colonization, Revolutionary War, and beyond, the Bay has been front and center, as it continues to do today. Chesapeake Bay is very much a part of the fabric of our nation.
(Above image: Image cred – AnneStClairWright.com. Historic photo of boats and ships in Annapolis Harbor. )
When I considered how to choose the best places to visit by boat, I wondered how difficult it would be to narrow down the list of choices. After all, “best” is a relative term, and subjective.
So, I chose places close enough to reach in a day, and capable of providing an on-water experience to satisfy the adventure and excitement we look for. A balance, if you will, between the journey and the destination.
I have not included details of channel entrances or other directions, which I leave to the ship’s navigator. Information in charts and sailing directions is widely available in several Chesapeake Bay cruising guides and online resources. Putting together a plan for an upcoming cruise is always a fun and learning activity for those with Chesapeake Bay on their horizon.
ANNAPOLIS
The top place I recommend without question as a “must see” place to visit happens to be the starting point for most people but often overlooked. Annapolis is a wonderful place to begin one’s Chesapeake cruising, and one of the most popular places to visit in all of Chesapeake Bay, certainly for those who concentrate their boating in the middle of the Bay.
Besides being the Sailing Capital of the U.S., Annapolis has a rich history that originates with our country’s early settlers. It developed as a prominent seaport for a growing nation, a center for commerce and the global business of the time. (Annapolis and Oxford were official ports of entry in the late 1600s for all British and European ships arriving to do business with the Maryland Colony.) It went on to become the state capital and even the nation’s capital for a time in the newly formed United States of America.
One finds exceptional 1700-era Georgian homes and estates built and occupied by prominent nation builders. Four of the signers of the Declaration of Independence were residents of Annapolis. (There are more surviving 18th Century buildings here than any other city in the country.)
Annapolis is a popular destination for history buffs, boaters, seasoned travelers, and nature lovers. It is famous for its colonial heritage, dining, accommodations, and entertainment. Guided tours of downtown, a walkabout around the Naval Academy, and watching midweek sailboat races are all part of the fun.
And it is not just for out-of-town tourists. Locals who frequent Annapolis for shopping, boat shows, and seafood know what a special treat it is to arrive by boat instead of driving. The come-by-boat experience is like a mini-vacation. A mooring in Spa Creek for a couple of days is a proper getaway in every sense of the word.
ST. MICHAELS
Named one of the Top 10 Best Small Coastal Towns in America by USA Today, St. Michaels ranks at the top of cruising destinations on Chesapeake Bay. It has a lot to offer: picturesque neighborhoods, shopping, tasty food, and all sorts of events and activities in an old waterfront town on the Eastern Shore. Whatever strikes your fancy, there is something fun to do here.
St. Michaels is home of the Chesapeake Bay Maritime Museum, an 18-acre campus that offers interactive exhibits about the natural, cultural, and geographical elements of the Chesapeake’s maritime world, past and present. Shipbuilding might seem the hub of the museum’s focus, but it goes well beyond into many other aspects of Chesapeake life, including art, waterfowl sports, and maritime history that celebrates a delicate marine environment.
The St. Michaels Museum at St. Mary’s Square is also a worthwhile visit. The museum offers several docent-led tours around the historic town, providing a glimpse of what life was like in the waterfront town 200 years ago. (There is plenty of information to do a self-guided tour if timing does not allow for the 90 minutes of the docent experience.)
A stroll down Talbot Street is fun for all crew members any day of the week, as there are many shops, pubs, galleries, and eateries to pull you in. I have been surprised more than once to find unusual and attractive clothing and accessories in shops where I only expected to find touristy tchotchkes or the inevitable assortment of refrigerator magnets. And every cruiser has fond memories of enjoying an ice cream cone during a sizzling summer day while people watching along the waterfront. Some restaurants specialize in seafood, while others offer great pizza, American fare, and something for everyone.
As dog friendly as it gets, St. Michaels is well worth a visit on any Chesapeake boating itinerary. Guides and maps are available online to plan one’s visit to this charming and historic port on the Eastern Shore.
For those continuing to other destinations, St. Michaels is a good stop to reprovision. Groceries are within walking distance of the various marinas in town, as are wine shops and other specialty stores.
Given its enormous popularity during the summer, it is best to make reservations when planning a visit.
Boats from around the world make a point of stopping in St. Michaels, so it is no surprise to see flags and burgees from everywhere.
St. Michaels is one of the most popular destinations on Chesapeake Bay for people looking to experience Bay boating.
(Chesapeake Bay Maritime Museum in St. Michaels, Maryland. Image Cred: Chesapeake Bay Maritime Museum)
CHESTERTOWN
Another quintessential colonial town, Chestertown dates back to the early 1700s, and much of its surviving architecture, brick sidewalks, and area mansions are testament to the town’s importance back in the day. A vitally important port town and commercial hub, it was as important as Annapolis to the future of the Maryland Colony.
Today, Chestertown is a wonderful blend of history, a vibrant local artist community, and the youthful impact of being a college town. Washington College received help from George Washington himself, and today is the 10th oldest college in the U.S.
The downtown main streets have art galleries, specialty shops, bakeries, bookstores, and historic buildings. There are ongoing exhibits that almost guarantee to keep the whole crew happily engaged for a weekend or more.
One aspect of cruising to Chestertown makes it a personal favorite for Chesapeake-style boating. After sailing the wide-open Bay to pass beneath the Bay Bridge from Annapolis, the rest of the trip after rounding Love Point on the tip of Kent Island is a 25-mile meander up the Chester River to Chestertown. It is a scenic adventure, with many side coves and neat anchorages that beckon cruisers not on a schedule. The lure of the river stands in sharp contrast to big water boating. There are miles of twisting bends and curves along settled farmlands, with natural thickets of trees ideal for bird watching. It can create a magic and lasting memory.
SOLOMONS
One of the favorites of all Chesapeake boaters stands at the entrance to the Patuxent River, about 45 miles from downtown Annapolis. Solomons is less about spectacular colonial architecture or history. It is just a cool place to go. It has a bit of everything, from shopping, restaurants, marine services, nature walks, and a relaxed atmosphere. And a trip to Solomons from Annapolis takes one past the famed Thomas Point Light, Calvert Cliffs, and perhaps even a stern warning on VHF to avoid gunnery practice from attack planes from Patuxent Naval Air Station.
Solomons is typically the first overnight stop of cruisers heading south to Florida after the fall boat shows. It is just far enough in distance to sort out things aboard, find out what’s missing or not working, and enjoy the calm from being somewhere that is familiar. Returning sailors in the spring find it just as comforting when their home destination is just over the horizon, as one anticipates seeing the Bay Bridge and radio towers of Annapolis the following day.
Many sailors race from Annapolis to Solomons in annual events, and it is on enough club summer cruises that over time most boaters develop familiarity coming into Solomons and the Patuxent area. They can relax with its easy access and numerous places to dock, eat, and experience.
Calvert Marine Museum is worth a visit, as it illustrates the life and history around Chesapeake Bay. Wood carvings and ship models provide an unusual perspective of the area, and there are environment and marine exhibits to educate and entertain. Even the fossil artifacts found nearby offer insight into the history of the Bay well before our time, adding another dimension to our appreciation of the world around us.
Many establishments, local artists, and restaurants are within walking distance of marinas, and it always feels good to stretch one’s legs after a day on the water.
(Drum Point Lighthouse located in Solomons, Maryland.)
One highlight worth a nod is the Annmarie Sculpture Garden and Arts Center, a 30-acre arts and nature center a couple of miles from the waterfront. It is a five-minute ride by bicycle or Uber and well worth the side trip for a walk through its gardens and gallery buildings.
Anyone who plans to become conversant in Chesapeake cruising should consider Solomons a requirement for the local experience.
And the roar coming from military aircraft zooming out of Patuxent NAS rings the bell of freedom to remind us of all we can be thankful for.
INNER HARBOR
To offer a stark counterpoint to the relaxing and natural destinations on my list of must-see places on Chesapeake Bay, it is only proper to include another stop that defines the other end of the energy and excitement spectrum. It is only 17 miles from Annapolis: Baltimore’s Inner Harbor.
Described in the 1980s by the American Institute of Architects as “one of the supreme achievements of large-scale urban design and development,” the Inner Harbor is a magnet for all kinds of reasons. It is the ultimate expression of post-industrial waterfront renewal.
Unlike most other Chesapeake Bay destinations, my advice is to arrange a slip at one of the many modern marinas along the Inner Harbor waterfront. While there are suitable and safe places to anchor, there is just too much to do and see here. You and your crew will prefer the convenience of stepping off the boat and walking or taking a water taxi to any number of compelling attractions. Area marinas have gated security to ensure personal safety, so cruisers can enjoy their time downtown.
There is the USS Constellation, the last surviving sailing warship of the U.S. Navy. There is also a World War II submarine, the USS Torsk, the lightship Chesapeake, and one of the last remaining lighthouses that stood online until 1948.
(Image: USS Constellation located in Baltimore’s Inner Harbor. Image Cred: BaltimoreBlueway.org.)
One can casually stroll over to the National Aquarium, the American Visionary Arts Museum, the Maryland Science Center (and its outstanding planetarium), and there is more. If baseball season has a home game on the schedule, it is only a short walk to Oriole Park at Camden Yards. Just follow the rest of the crowd leaving their boats to get a slice of a true American pastime, complete with beer and hot dogs.
To say there is always a lot to do is a major understatement. There are dozens of shops, restaurants, pubs, galleries, and coffee bars found nearby. Depending on where your boat is, you are only a fun water-taxi ride away from Fells Point, Canton, and other neighborhoods that offer their own local flavor and cultural spin. One can visit Fort McHenry, made famous during the War of 1812 when undaunted American defenders successfully beat off a relentless 24-hour bombardment of a large British fleet. The achievement so inspired Francis Scott Key to write what would become our National Anthem, The Star-Spangled Banner.
The Inner Harbor waterfront is near to Lexington Market which has been in continuous operation for over 200 years. One can spend an afternoon walking among the stalls, grills, and stands that serve the community as they have for generations. From sticky buns to crab cakes, jelly rolls to spring rolls, it is all here.
During the summer, the Inner Harbor is home to music and art festivals, waterfront races and other extraordinary events—like commissioning ceremonies of new ships in the Navy fleet.
A visit to the Inner Harbor is quite an experience.
THE BAY IS YOUR OYSTER
I could have gone on to list the top 10 Best Places, or the top 25. Chesapeake Bay is never at a loss to offer us memory-making adventures for anyone with a boat. Whether you have a powerboat or a sailboat, there are endless places to explore during the year, and don’t be surprised if each is different the next time you visit, particularly if the timing is earlier or later in the season.
The key is to get out there and go boating!
Crusader Yachts is your headquarters for boats for sale in Annapolis and the Chesapeake Bay area. We are new boat dealers for Excess Catamarans, Jeanneau Sailboats, and Tartan Yachts, as well as offer professional yacht brokerage services. Come see us at our office located at 7350 Edgewood Road in Annapolis or give us a call at (410) 269-0939 for more information about boating in the Chesapeake Bay area!
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