Share on facebook

Chesapeake Bay Cruising

This enchanting estuary will bring you memorable adventures on your next vacation. These choppy waters are filled with numerous ports for you to enjoy the Chesapeake Bay cruising experience. Also, you can enjoy the vast selection of activities that are along the way for you and the family around the Maryland and Virginia areas. One minute you can be dropped off near forests and cliffs then the next to a sandy island. Cruise multiple areas of the Chesapeake Bay to see as much as you can with these main port towns. You can discover other points of interest like local eateries, lighthouses and state parks along the way. After you pick your best port towns, read along at the end for the best seasons to travel and more cruising tips.

Upper Chesapeake

Photo Credit:

Along the northern reaches of the bay, you can sail easily from port to port as the towns are within a short distance between each other. We are discussing the upper Chesapeake Bay Bridge area near the mouth of the Susquehanna River. These areas offer anchorages, all-around marinas and unique points of interest. Discover these main cruise ports in Maryland.

Rock Hall, north of Annapolis on the eastern shore, is a quaint town to ride the trolley that passes through the antique and craft stores. Also, explore the local events such as the fantasy weekend that includes kayak races, Caribbean beach parties and more. For serious sea-foodies visit the Waterman’s Crab House eatery with live music on Saturday nights. You can dock at the Haven Harbour Marina nearby.

Check Chestertown along the way, it is south of Rock Hall by the Chester River. You will be warped back into the past with its 18th-century homes and unique art galleries. Visit the Worton Creek Marina for docking.

Havre de Grace is on the Susquehanna River with intact anchorages ready for any adventure. It also offers you a break with swimming activities. It has a main docking point in the Tidewater Marina.

Other nearby marinas to consider are The Wellwood Marina in Charlestown.

Baltimore, MD

Photo Credit:

This is a main attraction for the Chesapeake Bay visitors. Baltimore has a vibrant Inner Harbor located in the heart of Chesapeake Bay. This big city hosts blocks of fine dining and pubs with casual lounges in the Harbor East. Also, its neighborhood nightlife is worth checking out after putting the kids to bed. This popular destination has day trips for the sight seers and major attractions include the National Aquarium, the Maryland Science Center and the American Visionary Art Museum. Don’t forget Edgar Allen Poe lived here, and they host a year round carnival of culture along with maritime shows. This major cruise port serves as a starting point for the vacation trips that sail to Bermuda, the Caribbean, the Bahamas and New England.

You can visit these main marinas: Harbor East Marina, Inner Harbor West, Weaver’s Marine Service and Baltimore Yacht Basin for your cruising.

Annapolis, MD

Referred to as the boating capital of the bay, is plentiful in marinas and history in the city.
This city offers sightseeing endeavors everywhere you turn. Take a walking tour to reveal the eye-catching buildings all around you. A few architecture styles are the Georgian, Greek Revival and Federal from the early 1900s. If you are planning a family outing visit the nautical-themed boutiques and Graul’s Market to snack on their produce, meat and fish. Known for its sailing heritage, you can enjoy the dockside bars and restaurants. Visit the tailored shops for those new additions you’ve been wanting on your boat in Spa Creek or Back Creek. To the East, you can also take a trip to Kent Island nearby.

A few main marinas nearby are the Annapolis Yacht Charter, Port Annapolis Marina, Pier 4 Marina, Whitehall Bay and Port Williams Marina.

Upper-Middle Chesapeake

This is the heart of the Chesapeake Bay with around 12,000 miles of shoreline. It is filled with marsh and forest landscapes to die for, islands with white sandy beaches, and has been explored by Captain John Smith’s voyage. Doesn’t matter if you are traveling on the western or eastern side of the bay there are clear waters and plenty of ports nearby. This is near the Chesapeake Bay Bridge linked to the Potomac River that offers the most familiar boating towns hosting famous fish festivals, hideaways, hidden coves and resort marinas.

Photo Credit:

St Michaels, near the eastern shore, has its own history exhibiting restored vessels at the Chesapeake Bay Maritime Museum and you can participate in the boatbuilding activities. After a local lunch or dinner, go on a river retreats near Wye East River in Dividing Creek where you will capture an anchorage. It engulfs a hidden cove that is connected to a park. St. Michaels Marina, LLC is one of the main marinas.

Oxford, a charming village of 600 people, is within walking distance to their ferries, the Tred Avon River, and quaint markets that provide everyday essentials. The town offers a full-service marina, Safe Harbor Oxford.

Other port towns that serve the Chesapeake Bay Bridge area near the Potomac River are Deale and North Beach. Also, Kent Island features a nature park filled with wildlife. You can expect fishing, crabbing, local eateries and dancing to be common in these areas.

Lower Chesapeake

Photo Credit:

Brackish waters filled with flowing rivers that are mixed with the Atlantic Ocean is the Southeast part of the bay. Watch for the shallow waters near the sandy islands, inlets and small rivers. The distance between towns and weather conditions vary. There may be additional time and planning involved so keep notes on alternate ports just in case the waters turn on you. You can expect wider waters for cruising around this area and you are close to the Virginia port towns that have less traffic and simpler communities.

Tangier Island is the home for crab and oyster picking. It is known to be the world capital for soft shell crab. This unique small town houses around 600 people so everything is within walking distance. You can check out their local restaurants to grab a bite or visit the Daley & Sons grocery store. Talk with the locals as they know a few stories about the people and animals that were native there. They do offer simpler dock systems at the Parks Marina near the harbor channel.

Deltaville is on the western side of the bay. It has a surplus of marinas and boatyards with full service shops and supplies for a cruising destination. They have many fishing tournaments, festivals, sailing races and local eateries. If you are into the classics, they also have numerous consignment and antique shops for souvenirs. There are also local museums that recorded the significant historical moments along with Holly Point Park featuring outdoor sculptures for taking photos. Check out the Dozier’s Regatta Point, Stingray Point, Fishing Bay and Deltaville Yachting Center Marinas for Chesapeake Bay cruising.

Norfolk is a city known for the world’s largest naval base, the Naval Station Norfolk. Visit their museums for extra history lessons. The World War II battleship history is featured at the Nauticus maritime museum. Don’t miss the zoo and botanical garden too.

Yorktown is known for its legendary battle field for the last major battle in the Revolutionary War. You can dock at Wormley Creek Marina.

The cities of Hampton and Virginia Beach are also one of the busiest ports. They are great choices for visiting vessels as they meet the boating lifestyle with supplies and stores. They are also enriched with shopping, historical sites and fine dining along the waterways. And get ready for the entertainment. Bluewater Yachting Center is a nearby marina. Also, there are others such as Marina Shores in Virginia Beach along with Bell Isle Marina and Southall Landings Marina in Hampton.

Cruising Tips

Great seasons for Chesapeake Bay Cruising are during the spring to see more florals and the fall for its foliage. You may find discomfort in the summertime as it tends to be hot and sticky. Even late April to May or September to mid-October are excellent times for cruising.

With any destination, you might want to plan ahead. Create your own itinerary of where each port is able to stop and how they correlate in distance with other ports. Also, list other activities and outings you want to visit during this round trip excursion. You can maximize your traveling to the fullest and not miss any festival or outing. As the stops may be time consuming, this gives you an opportunity to explore on your own.

If you are traveling in the spring and fall, bring more clothing layers due to brisk winds and cooler weather. So pack away the right apparel. Also, during your time at Chesapeake Bay, it is usually a casual environment so leave the business attire at home.

Get Content like this sent directly to your inbox!