EXPLORING THE
CHESAPEAKE

22 Cruising Destinations For Your Mid-Atlantic Bucket List

Oct 23, 2017 | Bluewater Perspective, Featured, Magazine, News |

This article was excerpted from the Waterway Guide Chesapeake Bay 2017 edition. Thanks to our friends at Waterway Guide for their partnership in promoting safe boating and adventures in yachting.

The Chesapeake Bay is an immense, delightful and varied cruising ground. You can be in the midst of a large city with aircraft carriers and barges in the morning and by afternoon secured in a bucolic anchorage surrounded by a tall pine forest or undulating marsh grass. Your biggest challenge when cruising the Bay is deciding where to go and exploring it can be a lifelong adventure.

The destinations we have selected here are within a day’s reach for most cruising powerboats, and several of Bluewater’s sales and service offices are conveniently located nearby. While approximate mileages are given, keep in mind that factors outside your control can greatly affect your timeline. For example, a trip from the Patuxent to the Choptank in a northeaster could take many hours longer than the same trip on a calm day or with favorable winds. Also, your draft may allow you to take some of the many shortcuts on the Bay, such as the “back door” to St. Michaels or Kent Narrows to the Chester River. There are some great tools to plan your trip at waterwayguide.com. The maps, charts, information and other resources complement the Waterway Guide books and provide important insight and advice for your adventures.

The Lower Bay

The first thing you will notice is that the Bay is wide—up to 24 n.m. in some places—and distances between ports vary. Weather is always a factor, as seas can build from any direction depending on your location. The time required to move from port to port will require additional planning, with alternative destinations as a backup. The attraction is that, outside of the immediate Norfolk area, crowds are almost nonexistent and the pace is slow.

You may appreciate your cruise more if you have an understanding of the Bay, its history, traditions, boats, people and beauty. We recommend stops at one of the many maritime museums located in the southern Bay. These are noted in the descriptions below.

Norfolk and Portsmouth, Hampton Roads: Mile Zero of the Intracoastal Waterway (ICW) begins at Norfolk and Portsmouth, thus making this a natural starting point for your tour of the southern Bay. This area is one of the busiest ports in the U.S. and home to the largest naval base in the world. The cities of Hampton, Newport News, Portsmouth, Norfolk, Chesapeake and Virginia Beach cater to the lifestyle and needs of boaters. It is also where the first Bluewater Yacht Sales location was established, nearly 50 years ago. Known as Hampton Roads, this nautical crossroad is home to vessels of all kinds (and sizes), as well as the amenity-rich Bluewater Yachting Center. Museums, historic sites, shopping and dining line the waterways, providing days, or even weeks, of entertainment possibilities.

Yorktown, York River: About 20 n.m. to the north of Hampton Roads is historic Yorktown. Navigate to the quaint Riverwalk and take a slip in the center of the action. Shopping and dining abound, and you are in the Historic Triangle. If you plan to stay a few days, rent a car (or ride your bike) to the Yorktown Victory Center then head north on the Colonial Parkway to the historic towns of Williamsburg (21 miles) and Jamestown (an additional 18 miles). Gloucester Point’s York River Yacht Haven located at the mouth of Sarah Creek, opposite Yorktown, offer yet another full-service Bluewater Yacht Sales team at your beck and call. Storm-protected from every quadrant, this 14-acre rural site is in a natural “hurricane hole,” rich with marina and yard amenities and a great restaurant for romantic sunset dining.

Deltaville, Rappahannock and Piankatank Rivers: Staying on the western side of the Bay, you can spend a couple of days gunkholing or visiting the many marinas in the Middle Peninsula or Northern Neck. Tie up at the Tides Inn on Carter’s Creek or on either side of Deltaville and visit the Maritime Museum to see the history of the region and its dependence on boatbuilding and fishing.

Moving north on the western shore you’ll come across pleasant towns like Reedville on the Great Wicomico and St. Marys up the Potomac River. It is about 30 n.m. from Reedville to the mouth of the Potomac, and another 15 n.m. to the mouth of the St. Marys River on the north shore.

A notable St. Marys City tie-up is at the Teddy Turner Waterfront at St. Marys College. If you are looking for more options, Washington, DC via the Potomac River is rife with them. Stops here can run you a few days up to a few weeks, but are well worth the effort. The river is wide almost to Washington, D.C. (95 n.m. upstream) where you can step off the boat and walk to the Smithsonian museums and the Kennedy Center. On the way upriver, you will pass historic Mt. Vernon, upscale National Harbor and Old Town Alexandria.

Headed east on the Bay from the Potomac, take a step back in time by visiting Smith and Tangier Islands. These are not anchoring destinations; you will want to take a slip and completely immerse yourself in the culture of these unique communities. Folks drive their boats to work (crabbing on the Bay) and, on Tangier, golf carts to dinner at establishments such as Hilda Crockett’s Chesapeake House (circa 1939) with family-style dining. Smith Island is known for its multi-layered cakes, originally sent out with husbands during oyster season and now designated as the “Official Cake of the State of Maryland.” Head back west from Smith Island about 30 n.m. to the Patuxent River and you’ll find the interesting village of Solomons with nice restaurants, good shopping, extensive marina facilities and many peaceful creeks just upriver of the bridge.

The Upper Bay

In the more northern reaches of the Bay you will have short hops and be able to easily crisscross from one port town to another. (The Bay is only about 3 n.m. wide at its narrowest point, north of Gunpowder Neck)This stretch of the Bay offers quiet anchorages, well-equipped marinas and deep water. Tilghman Island, Choptank River and Tred Avon: The village of Oxford and the town of Cambridge both offer full-service marinas, good restaurants and ample provisioning opportunities.

St Michaels: From Oxford it’s about 30 n.m. to the town of St. Michaels. With its history and shopping, it is one of the most popular boating destinations on the Bay. The village is quaint and pretty, and there are many quiet rivers nearby for a retreat after you have visited the impressive Chesapeake Bay Maritime Museum. Plan to spend a day here, exploring the working boatyard and the 1879 Hooper Strait Lighthouse. One of the most idyllic gunkholes of the entire Bay is 8 n.m. north in the Wye East River in Dividing Creek. This anchorage is in the tree-surrounded cove of an island, most of which is a park.

Annapolis, Severn River: When you are ready to pick up the pace and immerse in American history then head to Annapolis, the undisputed boating capital of the Chesapeake. It’s home to the U.S. Naval Academy. Spa Creek, Back Creek and the surrounding areas have an immense number of boat-related shops, both repair and retail. This is one of the best places to shop around for anticipated boat projects, improvements, or new additions. There are many excellent restaurants within walking distance of the water, and the sightseeing and shopping in the historic area should not be missed.

To the east of Annapolis lies Kent Island and Narrows, where Mears Point Marina hosts our Grasonville team. Kent Narrows offers an ideal summer stop for cracking crabs and a world famous “Red Eye” to wash it down—so famous, there’s even a dock bar named after it. On a typical summer weekend, you’ll find crowds gathered for great live music as well. Heading up the Chester River you’ll be taken into the very heart of the Eastern Shore countryside. You will want to plan a lay day to enjoy Chestertown. Or come out of the Chester River and head 12 n.m. north to the quaint town of Rock Hall and Swan Creek.

Once you have overindulged yourself with woods, marsh and field, you can re-enter civilization with Baltimore’s big-city sights and amenities. Baltimore Marine Center at Lighthouse Point is nestled along the waterfront of Canton, just east of Fells Point and across from historic Fort McHenry. This popular destination offers ideal daytrips into the city and nearby attractions—museums, restaurants, historical sites, shopping and a constant carnival of cultural, ethnic and maritime shows. Or you can opt to just enjoy the towering cityscape view and active harbor traffic from your slip at this finely tuned facility—complete with Bluewater’s northernmost sales office and a team eager to help ensure your boating satisfaction.

The Chesapeake then meanders past Baltimore to the pristine anchorages and good swimming holes of Georgetown on the Sassafras River and Havre de Grace on the Susquehanna River. Beyond that, you’ll find Turkey Point, where the channel heads NE to the Chesapeake and Delaware Canal, connecting Delaware Bay and the Atlantic Intracoastal Waterway to New Jersey, Pennsylvania and New York.

The Chesapeake Bay is truly one of the best cruising grounds in the world. You can almost always find a lee to anchor in and there are unlimited opportunities for docking, exploring and going ashore. Feel free to stop in at any of our Bluewater locations and visit along the way. We’ll be happy to see you and provide some inside tips and local knowledge to make your time on the Chesapeake even more memorable—as you cruise the “land of pleasant living.”