Our Favorite Places To Visit by Boat on the Chesapeake Bay

From small historic waterfront towns on the eastern shore to resort style marinas, Chesapeake Bay has many favorite destinations for boaters

We have been boating on the Chesapeake Bay for over 20 years now, and never seem to grow tired of visiting our favorite places and discovering new ones on the bay.

The Chesapeake Bay is an enormous body of water that spans from Delaware to Virginia, and is made up of numerous rivers and tributaries. Most of the boating destinations consist of bigger cities & towns on the western shore, and smaller waterfront towns on the eastern shore. Each place brings a unique experience for us as boaters. As upper bay boaters, most of our boat trips are to destinations in Maryland.

Here are some of my favorite places to visit by boat on the Chesapeake Bay.

Annapolis Maryland

Our #1 place to visit every year is Annapolis Maryland. We love the historic nautical town loaded with some of the best shops, bars and restaurants in Maryland. For our family the seafood, and in particular Chesapeake Bay crabcakes, is the biggest reason we keep coming back again & again. You'll typically find us at our favorite bar Middleton's Tavern devouring endless orders of mussels, crabcakes and oyster shooters.

In the fall they have 2 big boat shows - Annapolis U.S. Powerboat Show and Annapolis U.S. Sailboat Show. I have been to both many times and of course as a powerboater prefer the power show. Here are a few videos of past shows!

Rock Hall Maryland

Our favorite small town to visit by boat on the eastern shore of the Chesapeake Bay is Rock Hall. We didn't even know this town existed until we got into boating!

Rock Hall is a small waterman's town where their main industry is crabbing. Just north of the Bay Bridge, it has easy access to most areas of the Chesapeake Bay. Its small town vibes is always a very relaxing time when we visit.

Our favorite marina to stay at is Haven Harbour on Swan Creek. In fact, it was a visit to this marina as guests that got us into boating! The marina is packed with amenities and is always a pleasure to visit. They also have a great service department and stayed there almost a month while we had work done on our boat. Check out our Rock Hall videos to see more!

Baltimore Maryland

If you want more of a city experience, then you need to stop by Baltimore Inner Harbor. Located just north of the Bay Bridge on the western shore, Baltimore is one of the biggest cities on the Chesapeake Bay (second to Washington DC).

The town is full of activities for the family to explore, like the National Aquarium and Science Museum. And of course there's tons of shopping and restaurants to visit. We like to stay right in Inner Harbor so we have the view of the skyline at night. Marinas like Baltimore Inner Harbor (next to the popular seafood restaurant Rusty Scupper) have gated access so you can feel secure in the city environment.

Cambridge & North Beach

Two marinas with resort-like locations are actually located south of the Bay Bridge on opposite sides of the bay. These two places are more marina destinations then town/city destinations on the Chesapeake Bay.

Cambridge Maryland is on the eastern shore and is home to the Hyatt Cambridge Resort & Marina and is the only hotel resort marina on the bay. Although the marina itself is very basic, you get access to all the resort amenities at the hotel - like multiple pools, restaurants, beach activities, mini golf and more.

Herrington Harbour South Marina is located in North Beach Maryland and is on the western shore. HH South is a beautiful property and includes a marina as well as an inn and restaurant. There's also a beach area with complimentary kayaks and paddleboards, and a huge Olympic sized pool. The property is so beautiful that it hosts a LOT of weddings so I'd recommend a less busy weekday visit.

Check out videos of both of our visits to these places on the Chesapeake Bay!

Sassafras River

Finally, we love our home port on the beautiful Sassafras River. There are multiple anchorages on the Sassafras to drop a hook in the sandy bottom of the river and enjoy a swim. In fact, because the water is more brackish than locations further south, we never have any issue with sea nettles (aka jellyfish). When we are not traveling to one our other favorite places on the Chesapeake Bay you can usually find us on the hook here.