Best Chesapeake Bay Boating Destinations

Countdown of the 5 best boating destinations for boaters on the upper Chesapeake Bay

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. In fact some years we’ll go to the same place twice.

And then other years we’ll add a new one into the mix that we haven’t been to for years or ever before.

If you’re not familiar with the Chesapeake Bay, it’s an enormous body of water that spans from Delaware to Virginia, and is made up of numerous rivers and tributaries. You really could spend a lifetime exploring the bay.

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.

So here’s a rundown of our top 5 best boating destinations on the Chesapeake Bay we like to go to by boat.

#5 Cambridge, Maryland

Cambridge is on the eastern shore south of the Bay Bridge and home to the Hyatt Cambridge Resort & Marina.
If you’re longing for more of a resort getaway, then its worth the cruise up the Choptank River to the Hyatt Resort & Marina. Its really the only hotel resort marina on the bay.

Although the marina itself is very basic, some can even argue that the docks are in pretty rough shape, when you stay there you get full access to all the resort amenities at the hotel – like multiple pools, restaurants, beach activities, mini golf and more. There’s definitely no other marina that has this level of amenities on the bay.

#4 North Beach, Maryland

A short cruise back up Choptank and across the bay takes you to North Beach.

Herrington Harbour has two marinas located on the western shore – South & North. There is a big debate on the bay about which property is the “best” but we prefer Herrington Harbour South Marina located in North Beach Maryland.

Herrington Harbour South is an absolutely beautiful property and includes a marina as well as an inn and restaurant. There’s a beach area with kayaks and paddleboards, and a huge Olympic sized pool… the biggest pool we’ve been to on the bay! The property is so beautiful that it hosts a LOT of weddings so I’d recommend a less busy weekday visit.

#3 St. Michaels, Maryland

Our favorite small town to visit by boat is St. Michael’s Maryland. St. Michaels is located just a bit further south than Annapolis and on the eastern shore of the Chesapeake Bay. The main harbor is very tight and busy – especially on the weekends.

It’s a very small town so EVERYTHING is within walking distance… and there’s surprisingly a lot to do. Great restaurants and bars, and lots of shopping. Like most of the waterfront towns it’s a historic location on the bay – and there’s even a maritime museum right in the harbor.

#2 Rock Hall, Maryland

Another favorite 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 vibe is always a very relaxing time when we visit. Most people walk or bike around town. And there’s lots of events going on like their famous Pirates & Wenches weekend in the summer or Oyster Fest in the fall.

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 0ver 20 years ago – so it feels like home to us! There’s a lot to do at the marina… with a pool, lawn games and outside bar. And if you’re boating with friends they can even rent a room at their Inn.

#1 Annapolis Maryland

Our #1 boating destination 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.

They have a water taxi that makes it easy to stay at pretty much any marina in the area and then take a short cruise to where all the action is at city dock.
For our family the seafood is the biggest reason we keep coming back again & again – although to be honest we are usually all about the seafood everywhere we go on the bay! In Annapolis, you’ll typically find us at our favorite bar Middleton’s Tavern devouring endless orders of mussels, crabcakes and oyster shooters.

We love it so much that we often go back for a visit in the fall when they have 2 of the biggest boat shows on the east coast – the Annapolis U.S. Powerboat Show and the Annapolis U.S. Sailboat Show.

More to Explore

Each year we try to add at least one new destination on our list to check out. There are so many amazing small towns and marinas to explore on the Chesapeake Bay. It really is a boater’s paradise!